docs: clarify that Credentials::new takes bearer token for xoauth2

Support WASM environments by using web-time.
This was tested on a Cloudflare worker environment.

.editorconfig

@@ -0,0 +1,8 @@
+root = true
+
+[*]
+insert_final_newline = true
+
+[*.rs]
+indent_size = 4
+indent_style = space

.github/workflows/test.yml

@@ -7,20 +7,22 @@ on:
       - master
 
 env:
+  RUSTFLAGS: "--cfg lettre_ignore_tls_mismatch"
+  RUSTDOCFLAGS: "--cfg lettre_ignore_tls_mismatch"
   RUST_BACKTRACE: full
 
 jobs:
   rustfmt:
-    name: rustfmt / stable
+    name: rustfmt / nightly-2024-09-01
     runs-on: ubuntu-latest
 
     steps:
       - name: Checkout
-        uses: actions/checkout@v2
+        uses: actions/checkout@v4
 
       - name: Install rust
         run: |
-          rustup update --no-self-update stable
+          rustup default nightly-2024-09-01
           rustup component add rustfmt
 
       - name: cargo fmt
@@ -32,7 +34,7 @@ jobs:
 
     steps:
       - name: Checkout
-        uses: actions/checkout@v2
+        uses: actions/checkout@v4
 
       - name: Install rust
         run: |
@@ -48,25 +50,19 @@ jobs:
 
     steps:
       - name: Checkout
-        uses: actions/checkout@v2
-
-      - name: Setup cache
-        uses: actions/cache@v2
-        with:
-          path: |
-            ~/.cargo/registry
-            ~/.cargo/git
-            target
-          key: ${{ runner.os }}-cargo-check
+        uses: actions/checkout@v4
 
       - name: Install rust
         run: rustup update --no-self-update stable
-      
+
+      - name: Setup cache
+        uses: Swatinem/rust-cache@v2
+
       - name: Install cargo hack
         run: cargo install cargo-hack --debug
 
       - name: Check with cargo hack
-        run: cargo hack check --feature-powerset --depth 3
+        run: cargo hack check --feature-powerset --depth 3 --at-least-one-of aws-lc-rs,ring --at-least-one-of rustls-native-certs,webpki-roots
 
   test:
     name: test / ${{ matrix.name }}
@@ -79,28 +75,22 @@ jobs:
             rust: stable
           - name: beta
             rust: beta
-          - name: 1.45.2
-            rust: 1.45.2
+          - name: '1.74'
+            rust: '1.74'
 
     steps:
       - name: Checkout
-        uses: actions/checkout@v2
-
-      - name: Setup cache
-        uses: actions/cache@v2
-        with:
-          path: |
-            ~/.cargo/registry
-            ~/.cargo/git
-            target
-          key: ${{ runner.os }}-cargo-test-${{ matrix.rust }}
+        uses: actions/checkout@v4
 
       - name: Install rust
         run: |
           rustup default ${{ matrix.rust }}
           rustup update --no-self-update ${{ matrix.rust }}
 
-      - name: Install postfix  
+      - name: Setup cache
+        uses: Swatinem/rust-cache@v2
+
+      - name: Install postfix
         run: |
           DEBIAN_FRONTEND=noninteractive sudo apt-get update
           DEBIAN_FRONTEND=noninteractive sudo apt-get -y install postfix
@@ -108,20 +98,37 @@ jobs:
       - name: Run SMTP server
         run: smtp-sink 2525 1000&
 
+      - name: Install coredns
+        run: |
+          wget -q https://github.com/coredns/coredns/releases/download/v1.8.6/coredns_1.8.6_linux_amd64.tgz
+          tar xzf coredns_1.8.6_linux_amd64.tgz
+
+      - name: Start coredns
+        run: |
+          sudo ./coredns -conf testdata/coredns.conf &
+          sudo systemctl stop systemd-resolved
+          echo "nameserver 127.0.0.54" | sudo tee /etc/resolv.conf
+
+      - name: Install dkimverify
+        run: sudo apt -y install python3-dkim
+
       - name: Test with no default features
         run: cargo test --no-default-features
 
       - name: Test with default features
         run: cargo test
 
-      - name: Test with all features
-        run: cargo test --all-features
-  
+      - name: Test with all features (-native-tls)
+        run: cargo test --no-default-features --features async-std1,async-std1-rustls,aws-lc-rs,rustls-native-certs,boring-tls,builder,dkim,file-transport,file-transport-envelope,hostname,mime03,pool,rustls-native-certs,rustls,sendmail-transport,smtp-transport,tokio1,tokio1-boring-tls,tokio1-rustls,tracing
+
+      - name: Test with all features (-boring-tls)
+        run: cargo test --no-default-features --features async-std1,async-std1-rustls,aws-lc-rs,rustls-native-certs,builder,dkim,file-transport,file-transport-envelope,hostname,mime03,native-tls,pool,rustls-native-certs,rustls,sendmail-transport,smtp-transport,tokio1,tokio1-native-tls,tokio1-rustls,tracing
+
 #  coverage:
 #    name: Coverage
 #    runs-on: ubuntu-latest
 #    steps:
-#      - uses: actions/checkout@v2
+#      - uses: actions/checkout@v4
 #      - uses: actions-rs/toolchain@v1
 #        with:
 #          toolchain: nightly

.gitignore

@@ -4,4 +4,3 @@
 lettre.sublime-*
 lettre.iml
 target/
-/Cargo.lock

CHANGELOG.md

@@ -1,11 +1,451 @@
+<a name="v0.11.15"></a>
+### v0.11.15 (2025-03-10)
+
+#### Upgrade notes
+
+* MSRV is now 1.74 ([#1060])
+
+#### Features
+
+* Add controlled shutdown methods ([#1045], [#1068])
+
+#### Misc
+
+* Deny `unreachable_pub` lint ([#1058])
+* Bump minimum supported `rustls` ([#1063])
+* Bump minimum supported `serde` ([#1064])
+* Upgrade semver compatible dependencies ([#1067])
+* Upgrade `email-encoding` to v0.4 ([#1069])
+
+[#1045]: https://github.com/lettre/lettre/pull/1045
+[#1058]: https://github.com/lettre/lettre/pull/1058
+[#1060]: https://github.com/lettre/lettre/pull/1060
+[#1063]: https://github.com/lettre/lettre/pull/1063
+[#1064]: https://github.com/lettre/lettre/pull/1064
+[#1067]: https://github.com/lettre/lettre/pull/1067
+[#1068]: https://github.com/lettre/lettre/pull/1068
+[#1069]: https://github.com/lettre/lettre/pull/1069
+
+<a name="v0.11.14"></a>
+### v0.11.14 (2025-02-23)
+
+This release deprecates the `rustls-tls`, `tokio1-rustls-tls` and `async-std1-rustls-tls`
+features, which will be removed in lettre v0.12.
+
+rustls users should start migrating to the `rustls`, `tokio1-rustls` and
+`async-std1-rustls` features. Unlike the deprecated _*rustls-tls_ features,
+which automatically enabled the `ring` and `webpki-roots` backends, the new
+features do not. To complete the migration, users must either enable the
+`aws-lc-rs` or the `ring` feature. Additionally, those who rely on `webpki-roots`
+for TLS certificate verification must now explicitly enable its feature.
+Users of `rustls-native-certs` do not need to enable `webpki-roots`.
+
+Find out more about the new features via the [lettre rustls docs].
+
+#### Features
+
+* Make it possible to use different `rustls` crypto providers and TLS verifiers ([#1054])
+
+#### Bug fixes
+
+* Use the same `rustls` crypto provider everywhere ([#1055])
+
+#### Misc
+
+* Deprecate `AsyncNetworkStream` being public ([#1059])
+* Upgrade `nom` to v8 ([#1048])
+* Drop `rustls-pemfile` in favor of `rustls-pki-types` APIs ([#1050])
+* Ban direct use of `std::time::SystemTime::now` via clippy ([#1043])
+* Drop direct dependency on `rustls-pki-types` ([#1051])
+* Remove artifact from `web-time` refactor ([#1049])
+* Fix warnings with `rustls-native-certs` when `tracing` is disabled ([#1053])
+* Bump license year ([#1057])
+* Cleanup `Cargo.toml` style ([#1047])
+
+[lettre rustls docs]: https://docs.rs/lettre/0.11.14/lettre/index.html#smtp-over-tls-via-the-rustls-crate
+[#1043]: https://github.com/lettre/lettre/pull/1043
+[#1047]: https://github.com/lettre/lettre/pull/1047
+[#1048]: https://github.com/lettre/lettre/pull/1048
+[#1049]: https://github.com/lettre/lettre/pull/1049
+[#1050]: https://github.com/lettre/lettre/pull/1050
+[#1051]: https://github.com/lettre/lettre/pull/1051
+[#1053]: https://github.com/lettre/lettre/pull/1053
+[#1054]: https://github.com/lettre/lettre/pull/1054
+[#1055]: https://github.com/lettre/lettre/pull/1055
+[#1057]: https://github.com/lettre/lettre/pull/1057
+[#1059]: https://github.com/lettre/lettre/pull/1059
+
+<a name="v0.11.13"></a>
+### v0.11.13 (2025-02-17)
+
+#### Features
+
+* Add WASM support ([#1037], [#1042])
+* Add method to get the TLS verify result with BoringSSL ([#1039])
+
+#### Bug fixes
+
+* Synchronous pool shutdowns being arbitrarily delayed ([#1041])
+
+[#1037]: https://github.com/lettre/lettre/pull/1037
+[#1039]: https://github.com/lettre/lettre/pull/1039
+[#1041]: https://github.com/lettre/lettre/pull/1041
+[#1042]: https://github.com/lettre/lettre/pull/1042
+
+<a name="v0.11.12"></a>
+### v0.11.12 (2025-02-02)
+
+#### Misc
+
+* Warn against manually configuring `port` and `tls` on SMTP transport builder ([#1014])
+* Document variants of `Tls` enum ([#1015])
+* Fix rustdoc warnings ([#1016])
+* Add `ContentType::TEXT_PLAIN` to `Message` builder examples ([#1017])
+* Document `SmtpTransport` and `AsyncSmtpTransport` ([#1018])
+* Fix typo in transport builder `credentials` method ([#1019])
+* Document required system dependencies for OpenSSL ([#1030])
+* Improve docs for the `transport::smtp` module ([#1031])
+* Improve docs for smtp transport builder `from_url` ([#1032])
+* Replace `assert!` with `?` on `send` examples ([#1033])
+* Warn on more pedantic clippy lints and fix them ([#1035], [#1036])
+
+[#1014]: https://github.com/lettre/lettre/pull/1014
+[#1015]: https://github.com/lettre/lettre/pull/1015
+[#1016]: https://github.com/lettre/lettre/pull/1016
+[#1017]: https://github.com/lettre/lettre/pull/1017
+[#1018]: https://github.com/lettre/lettre/pull/1018
+[#1019]: https://github.com/lettre/lettre/pull/1019
+[#1030]: https://github.com/lettre/lettre/pull/1030
+[#1031]: https://github.com/lettre/lettre/pull/1031
+[#1032]: https://github.com/lettre/lettre/pull/1032
+[#1033]: https://github.com/lettre/lettre/pull/1033
+[#1035]: https://github.com/lettre/lettre/pull/1035
+[#1036]: https://github.com/lettre/lettre/pull/1036
+
+<a name="v0.11.11"></a>
+### v0.11.11 (2024-12-05)
+
+#### Upgrade notes
+
+* MSRV is now 1.71 ([#1008])
+
+#### Bug fixes
+
+* Fix off-by-one error reaching the minimum number of configured pooled connections ([#1012])
+
+#### Misc
+
+* Fix clippy warnings ([#1009])
+* Fix `-Zminimal-versions` build ([#1007])
+
+[#1007]: https://github.com/lettre/lettre/pull/1007
+[#1008]: https://github.com/lettre/lettre/pull/1008
+[#1009]: https://github.com/lettre/lettre/pull/1009
+[#1012]: https://github.com/lettre/lettre/pull/1012
+
+<a name="v0.11.10"></a>
+### v0.11.10 (2024-10-23)
+
+#### Bug fixes
+
+* Ignore disconnect errors when `pool` feature of SMTP transport is disabled ([#999])
+* Use case insensitive comparisons for matching login challenge requests ([#1000])
+
+[#999]: https://github.com/lettre/lettre/pull/999
+[#1000]: https://github.com/lettre/lettre/pull/1000
+
+<a name="v0.11.9"></a>
+### v0.11.9 (2024-09-13)
+
+#### Bug fixes
+
+* Fix feature gate for `accept_invalid_hostnames` for rustls ([#988])
+* Fix parsing `Mailbox` with trailing spaces ([#986])
+
+#### Misc
+
+* Bump `rustls-native-certs` to v0.8 ([#992])
+* Make getting started example in readme complete ([#990])
+
+[#988]: https://github.com/lettre/lettre/pull/988
+[#986]: https://github.com/lettre/lettre/pull/986
+[#990]: https://github.com/lettre/lettre/pull/990
+[#992]: https://github.com/lettre/lettre/pull/992
+
+<a name="v0.11.8"></a>
+### v0.11.8 (2024-09-03)
+
+#### Features
+
+* Add mTLS support ([#974])
+* Implement `accept_invalid_hostnames` for rustls ([#977])
+* Provide certificate chain for peer certificates when using `rustls` or `boring-tls` ([#976])
+
+#### Changes
+
+* Make `HeaderName` comparisons via `PartialEq` case insensitive ([#980])
+
+#### Misc
+
+* Fix clippy warnings ([#979])
+* Replace manual impl of `#[non_exhaustive]` for `InvalidHeaderName` ([#981])
+
+[#974]: https://github.com/lettre/lettre/pull/974
+[#976]: https://github.com/lettre/lettre/pull/976
+[#977]: https://github.com/lettre/lettre/pull/977
+[#980]: https://github.com/lettre/lettre/pull/980
+[#981]: https://github.com/lettre/lettre/pull/981
+
+<a name="v0.11.7"></a>
+### v0.11.7 (2024-04-23)
+
+#### Misc
+
+* Bump `hostname` to v0.4 ([#956])
+* Fix `tracing` message consistency ([#960])
+* Bump minimum required `rustls` to v0.23.5 ([#958])
+* Dropped use of `ref` syntax in the entire project ([#959])
+
+[#956]: https://github.com/lettre/lettre/pull/956
+[#958]: https://github.com/lettre/lettre/pull/958
+[#959]: https://github.com/lettre/lettre/pull/959
+[#960]: https://github.com/lettre/lettre/pull/960
+
+<a name="v0.11.6"></a>
+### v0.11.6 (2024-03-28)
+
+#### Bug fixes
+
+* Upgraded `email-encoding` to v0.3 - fixing multiple encoding bugs in the process ([#952])
+
+#### Misc
+
+* Updated copyright year in license ([#954])
+
+[#952]: https://github.com/lettre/lettre/pull/952
+[#954]: https://github.com/lettre/lettre/pull/954
+
+<a name="v0.11.5"></a>
+### v0.11.5 (2024-03-25)
+
+#### Features
+
+* Support SMTP SASL draft login challenge ([#911])
+* Add conversion from SMTP response code to integer ([#941])
+
+#### Misc
+
+* Upgrade `rustls` to v0.23 ([#950])
+* Bump `base64` to v0.22 ([#945])
+* Fix typos in documentation ([#943], [#944])
+* Add `Cargo.lock` ([#942])
+
+[#911]: https://github.com/lettre/lettre/pull/911
+[#941]: https://github.com/lettre/lettre/pull/941
+[#942]: https://github.com/lettre/lettre/pull/942
+[#943]: https://github.com/lettre/lettre/pull/943
+[#944]: https://github.com/lettre/lettre/pull/944
+[#945]: https://github.com/lettre/lettre/pull/945
+[#950]: https://github.com/lettre/lettre/pull/950
+
+<a name="v0.11.4"></a>
+### v0.11.4 (2024-01-28)
+
+#### Bug fixes
+
+* Percent decode credentials in SMTP connect URL ([#932], [#934])
+* Fix mimebody DKIM body-hash computation ([#923])
+
+[#923]: https://github.com/lettre/lettre/pull/923
+[#932]: https://github.com/lettre/lettre/pull/932
+[#934]: https://github.com/lettre/lettre/pull/934
+
+<a name="v0.11.3"></a>
+### v0.11.3 (2024-01-02)
+
+#### Features
+
+* Derive `Clone` for `FileTransport` and `AsyncFileTransport` ([#924])
+* Derive `Debug` for `SmtpTransport` ([#925])
+
+#### Misc
+
+* Upgrade `rustls` to v0.22 ([#921])
+* Drop once_cell dependency in favor of OnceLock from std ([#928])
+
+[#921]: https://github.com/lettre/lettre/pull/921
+[#924]: https://github.com/lettre/lettre/pull/924
+[#925]: https://github.com/lettre/lettre/pull/925
+[#928]: https://github.com/lettre/lettre/pull/928
+
+<a name="v0.11.2"></a>
+### v0.11.2 (2023-11-23)
+
+#### Upgrade notes
+
+* MSRV is now 1.70 ([#916])
+
+#### Misc
+
+* Bump `idna` to v0.5 ([#918])
+* Bump `boring` and `tokio-boring` to v4 ([#915])
+
+[#915]: https://github.com/lettre/lettre/pull/915
+[#916]: https://github.com/lettre/lettre/pull/916
+[#918]: https://github.com/lettre/lettre/pull/918
+
+<a name="v0.11.1"></a>
+### v0.11.1 (2023-10-24)
+
+#### Bug fixes
+
+* Fix `webpki-roots` certificate store setup ([#909])
+
+[#909]: https://github.com/lettre/lettre/pull/909
+
+<a name="v0.11.0"></a>
+### v0.11.0 (2023-10-15)
+
+While this release technically contains breaking changes, we expect most projects
+to be able to upgrade by only bumping the version in `Cargo.toml`.
+
+#### Upgrade notes
+
+* MSRV is now 1.65 ([#869] and [#881])
+* `AddressError` is now marked as `#[non_exhaustive]` ([#839])
+
+#### Features
+
+* Improve mailbox parsing ([#839])
+* Add construction of SMTP transport from URL ([#901])
+* Add `From<Address>` implementation for `Mailbox` ([#879])
+
+#### Misc
+
+* Bump `socket2` to v0.5 ([#868])
+* Bump `idna` to v0.4, `fastrand` to v2, `quoted_printable` to v0.5, `rsa` to v0.9 ([#882])
+* Bump `webpki-roots` to v0.25 ([#884] and [#890])
+* Bump `ed25519-dalek` to v2 fixing RUSTSEC-2022-0093 ([#896])
+* Bump `boring`ssl crates to v3 ([#897])
+
+[#839]: https://github.com/lettre/lettre/pull/839
+[#868]: https://github.com/lettre/lettre/pull/868
+[#869]: https://github.com/lettre/lettre/pull/869
+[#879]: https://github.com/lettre/lettre/pull/879
+[#881]: https://github.com/lettre/lettre/pull/881
+[#882]: https://github.com/lettre/lettre/pull/882
+[#884]: https://github.com/lettre/lettre/pull/884
+[#890]: https://github.com/lettre/lettre/pull/890
+[#896]: https://github.com/lettre/lettre/pull/896
+[#897]: https://github.com/lettre/lettre/pull/897
+[#901]: https://github.com/lettre/lettre/pull/901
+
+<a name="v0.10.4"></a>
+### v0.10.4 (2023-04-02)
+
+#### Misc
+
+* Bumped rustls to 0.21 and all related dependencies ([#867])
+
+[#867]: https://github.com/lettre/lettre/pull/867
+
+<a name="v0.10.3"></a>
+### v0.10.3 (2023-02-20)
+
+#### Announcements
+
+It was found that what had been used until now as a basic lettre 0.10
+`MessageBuilder::body` example failed to mention that for maximum
+compatibility with various email clients a `Content-Type` header
+should always be present in the message.
+
+##### Before
+
+```rust
+Message::builder()
+  // [...] some headers skipped for brevity
+  .body(String::from("A plaintext or html body"))?
+```
+
+##### Patch
+
+```diff
+ Message::builder()
+   // [...] some headers skipped for brevity
++  .header(ContentType::TEXT_PLAIN) // or `TEXT_HTML` if the body is html
+   .body(String::from("A plaintext or html body"))?
+```
+
+#### Features
+
+* Add support for rustls-native-certs when using rustls ([#843])
+
+[#843]: https://github.com/lettre/lettre/pull/843
+
+<a name="v0.10.2"></a>
+### v0.10.2 (2023-01-29)
+
+#### Upgrade notes
+
+* MSRV is now 1.60 ([#828])
+
+#### Features
+
+* Allow providing a custom `tokio` stream for `AsyncSmtpTransport` ([#805])
+* Return whole SMTP error message ([#821])
+
+#### Bug fixes
+
+* Mailbox displays wrongly when containing a comma and a non-ascii char in its name ([#827])
+* Require `quoted_printable` ^0.4.6 in order to fix encoding of tabs and spaces at the end of line ([#837])
+
+#### Misc
+
+* Increase tracing ([#848])
+* Bump `idna` to 0.3 ([#816])
+* Update `base64` to 0.21 ([#840] and [#851])
+* Update `rsa` to 0.8 ([#829] and [#852])
+
+[#805]: https://github.com/lettre/lettre/pull/805
+[#816]: https://github.com/lettre/lettre/pull/816
+[#821]: https://github.com/lettre/lettre/pull/821
+[#827]: https://github.com/lettre/lettre/pull/827
+[#828]: https://github.com/lettre/lettre/pull/828
+[#829]: https://github.com/lettre/lettre/pull/829
+[#837]: https://github.com/lettre/lettre/pull/837
+[#840]: https://github.com/lettre/lettre/pull/840
+[#848]: https://github.com/lettre/lettre/pull/848
+[#851]: https://github.com/lettre/lettre/pull/851
+[#852]: https://github.com/lettre/lettre/pull/852
+
+<a name="v0.10.1"></a>
+### v0.10.1 (2022-07-20)
+
+#### Features
+
+* Add `boring-tls` support for `SmtpTransport` and `AsyncSmtpTransport`. The latter is only supported with the tokio runtime. ([#797]) ([#798])
+* Make the minimum TLS version configurable. ([#799]) ([#800])
+
+#### Bug Fixes
+
+* Ensure connections are closed on abort. ([#801])
+* Fix SMTP dot stuffing. ([#803])
+
+[#797]: https://github.com/lettre/lettre/pull/797
+[#798]: https://github.com/lettre/lettre/pull/798
+[#799]: https://github.com/lettre/lettre/pull/799
+[#800]: https://github.com/lettre/lettre/pull/800
+[#801]: https://github.com/lettre/lettre/pull/801
+[#803]: https://github.com/lettre/lettre/pull/803
+
 <a name="v0.10.0"></a>
-### v0.10.0 (unreleased)
+### v0.10.0 (2022-06-29)
 
 #### Upgrade notes
 
 Several breaking changes were made between 0.9 and 0.10, but changes should be straightforward:
 
-* MSRV is now 1.45.2
+* MSRV is now 1.56.0
 * The `lettre_email` crate has been merged into `lettre`. To migrate, replace `lettre_email` with `lettre::message`
   and make sure to enable the `builder` feature (it's enabled by default).
 * `SendableEmail` has been renamed to `Email` and `EmailBuilder::build()` produces it directly. To migrate,
@@ -14,7 +454,7 @@ Several breaking changes were made between 0.9 and 0.10, but changes should be s
 
 #### Features
 
-* Add `tokio` 0.2 and 1.0 support
+* Add `tokio` 1 support
 * Add `rustls` support
 * Add `async-std` support. NOTE: native-tls isn't supported when using async-std for the smtp transport.
 * Allow enabling multiple SMTP authentication mechanisms
@@ -29,9 +469,11 @@ Several breaking changes were made between 0.9 and 0.10, but changes should be s
 * Refactor `TlsParameters` implementation to not expose the internal TLS library
 * `FileTransport` writes emails into `.eml` instead of `.json`
 * When the hostname feature is disabled or hostname cannot be fetched, `127.0.0.1` is used instead of `localhost` as EHLO parameter (for better RFC compliance and mail server compatibility)
+* The `sendmail` and `file` transports aren't enabled by default anymore.
 * The `new` method of `ClientId` is deprecated
 * Rename `serde-impls` feature to `serde`
-
+* The `SendmailTransport` now uses the `sendmail` command in current `PATH` by default instead of
+  `/usr/bin/sendmail`.
 
 #### Bug Fixes
 
@@ -52,7 +494,7 @@ Several breaking changes were made between 0.9 and 0.10, but changes should be s
 * Update `hostname` to 0.3
 * Update to `nom` 6
 * Replace `log` with `tracing`
-* Move CI to Github Actions
+* Move CI to GitHub Actions
 * Use criterion for benchmarks
 
 <a name="v0.9.2"></a>
@@ -222,6 +664,6 @@ Several breaking changes were made between 0.9 and 0.10, but changes should be s
 
 *  multipart support
 *  add non-consuming methods for Email builders
-* `add_header` does not return the builder anymore, 
+* `add_header` does not return the builder anymore,
   for consistency with other methods. Use the `header`
   method instead

CONTRIBUTING.md

@@ -1,6 +1,6 @@
 ## Contributing to Lettre
 
-The following guidelines are inspired from the [hyper project](https://github.com/hyperium/hyper/blob/master/CONTRIBUTING.md).
+The following guidelines are inspired by the [hyper project](https://github.com/hyperium/hyper/blob/master/CONTRIBUTING.md).
 
 ### Code formatting
 

Cargo.toml

@@ -1,7 +1,7 @@
 [package]
 name = "lettre"
 # remember to update html_root_url and README.md (Cargo.toml example and deps.rs badge)
-version = "0.10.0-alpha.5"
+version = "0.11.15"
 description = "Email client"
 readme = "README.md"
 homepage = "https://lettre.rs"
@@ -10,7 +10,8 @@ license = "MIT"
 authors = ["Alexis Mousset <contact@amousset.me>", "Paolo Barbolini <paolo@paolo565.org>"]
 categories = ["email", "network-programming"]
 keywords = ["email", "smtp", "mailer", "message", "sendmail"]
-edition = "2018"
+edition = "2021"
+rust-version = "1.74"
 
 [badges]
 is-it-maintained-issue-resolution = { repository = "lettre/lettre" }
@@ -18,33 +19,39 @@ is-it-maintained-open-issues = { repository = "lettre/lettre" }
 maintenance = { status = "actively-developed" }
 
 [dependencies]
-idna = "0.2"
-tracing = { version = "0.1.16", default-features = false, features = ["std"], optional = true } # feature
+email_address = { version = "0.2.1", default-features = false }
+chumsky = "0.9"
+idna = "1"
+
+## tracing support
+tracing = { version = "0.1.16", default-features = false, features = ["std"], optional = true }
 
 # builder
-hyperx = { version = "1", optional = true, features = ["headers"] }
-mime = { version = "0.3", optional = true }
-uuid = { version = "0.8", features = ["v4"] }
-rand = { version = "0.8", optional = true }
-quoted_printable = { version = "0.4", optional = true }
-base64 = { version = "0.13", optional = true }
-once_cell = "1"
-regex = { version = "1", default-features = false, features = ["std", "unicode-case"] }
+httpdate = { version = "1", optional = true }
+mime = { version = "0.3.4", optional = true }
+fastrand = { version = "2.0", optional = true }
+quoted_printable = { version = "0.5", optional = true }
+base64 = { version = "0.22", optional = true }
+email-encoding = { version = "0.4", optional = true }
 
 # file transport
-serde = { version = "1", optional = true, features = ["derive"] }
+uuid = { version = "1", features = ["v4"], optional = true }
+serde = { version = "1.0.110", features = ["derive"], optional = true }
 serde_json = { version = "1", optional = true }
 
-# smtp
-nom = { version = "6", default-features = false, features = ["alloc"], optional = true }
-r2d2 = { version = "0.8", optional = true } # feature
-hostname = { version = "0.3", optional = true } # feature
+# smtp-transport
+nom = { version = "8", optional = true }
+hostname = { version = "0.4", optional = true } # feature
+socket2 = { version = "0.5.1", optional = true }
+url = { version = "2.4", optional = true }
+percent-encoding = { version = "2.3", optional = true }
 
 ## tls
-native-tls = { version = "0.2", optional = true } # feature
-rustls = { version = "0.19", features = ["dangerous_configuration"], optional = true }
-webpki = { version = "0.21", optional = true }
-webpki-roots = { version = "0.21", optional = true }
+native-tls = { version = "0.2.9", optional = true } # feature
+rustls = { version = "0.23.18", default-features = false, features = ["logging", "std", "tls12"], optional = true }
+rustls-native-certs = { version = "0.8", optional = true }
+webpki-roots = { version = "0.26", optional = true }
+boring = { version = "4", optional = true }
 
 # async
 futures-io = { version = "0.3.7", optional = true }
@@ -52,59 +59,93 @@ futures-util = { version = "0.3.7", default-features = false, features = ["io"],
 async-trait = { version = "0.1", optional = true }
 
 ## async-std
-async-std = { version = "1.8", optional = true, features = ["unstable"] }
-#async-native-tls = { version = "0.3.3", optional = true }
-async-rustls = { version = "0.2", optional = true }
+async-std = { version = "1.8", optional = true }
+futures-rustls = { version = "0.26", default-features = false, features = ["logging", "tls12"], optional = true }
 
 ## tokio
-tokio02_crate = { package = "tokio", version = "0.2.7", features = ["fs", "process", "tcp", "dns", "io-util"], optional = true }
-tokio02_native_tls_crate = { package = "tokio-native-tls", version = "0.1", optional = true }
-tokio02_rustls = { package = "tokio-rustls", version = "0.15", optional = true }
-tokio1_crate = { package = "tokio", version = "1", features = ["fs", "process", "net", "io-util"], optional = true }
+tokio1_crate = { package = "tokio", version = "1", optional = true }
 tokio1_native_tls_crate = { package = "tokio-native-tls", version = "0.3", optional = true }
-tokio1_rustls = { package = "tokio-rustls", version = "0.22", optional = true }
+tokio1_rustls = { package = "tokio-rustls", version = "0.26", default-features = false, features = ["logging", "tls12"], optional = true }
+tokio1_boring = { package = "tokio-boring", version = "4", optional = true }
+
+## dkim
+sha2 = { version = "0.10", features = ["oid"], optional = true }
+rsa = { version = "0.9", optional = true }
+ed25519-dalek = { version = "2", optional = true }
+
+## web-time for wasm support
+web-time = { version = "1.1.0", optional = true }
 
 [dev-dependencies]
-criterion = "0.3"
-tracing-subscriber = "0.2.10"
+pretty_assertions = "1"
+criterion = "0.5"
+tracing = { version = "0.1.16", default-features = false, features = ["std"] }
+tracing-subscriber = "0.3"
 glob = "0.3"
 walkdir = "2"
-tokio02_crate = { package = "tokio", version = "0.2.7", features = ["macros", "rt-threaded"] }
 tokio1_crate = { package = "tokio", version = "1", features = ["macros", "rt-multi-thread"] }
 async-std = { version = "1.8", features = ["attributes"] }
 serde_json = "1"
-maud = "0.22.1"
+maud = "0.26"
 
 [[bench]]
 harness = false
 name = "transport_smtp"
 
+[[bench]]
+harness = false
+name = "mailbox_parsing"
+
 [features]
-default = ["file-transport", "file-transport-envelope", "smtp-transport", "native-tls", "hostname", "r2d2", "sendmail-transport", "builder"]
-builder = ["mime", "base64", "hyperx", "rand", "quoted_printable"]
+default = ["smtp-transport", "pool", "native-tls", "hostname", "builder"]
+builder = ["dep:httpdate", "dep:mime", "dep:fastrand", "dep:quoted_printable", "dep:email-encoding"]
+mime03 = ["dep:mime"]
 
 # transports
-file-transport = []
-file-transport-envelope = ["serde", "serde_json", "file-transport"]
-sendmail-transport = []
-smtp-transport = ["base64", "nom"]
+file-transport = ["dep:uuid", "tokio1_crate?/fs", "tokio1_crate?/io-util"]
+file-transport-envelope = ["serde", "dep:serde_json", "file-transport"]
+sendmail-transport = ["tokio1_crate?/process", "tokio1_crate?/io-util", "async-std?/unstable"]
+smtp-transport = ["dep:base64", "dep:nom", "dep:socket2", "dep:url", "dep:percent-encoding", "tokio1_crate?/rt", "tokio1_crate?/time", "tokio1_crate?/net"]
 
-rustls-tls = ["webpki", "webpki-roots", "rustls"]
+pool = ["dep:futures-util"]
+
+rustls = ["dep:rustls"]
+aws-lc-rs = ["rustls?/aws-lc-rs"]
+fips = ["aws-lc-rs", "rustls?/fips"]
+ring = ["rustls?/ring"]
+webpki-roots = ["dep:webpki-roots"]
+# deprecated
+rustls-tls = ["webpki-roots", "rustls", "ring"]
+
+boring-tls = ["dep:boring"]
 
 # async
-async-std1 = ["async-std", "async-trait", "futures-io", "futures-util"]
-#async-std1-native-tls = ["async-std1", "native-tls", "async-native-tls"]
-async-std1-rustls-tls = ["async-std1", "rustls-tls", "async-rustls"]
-tokio02 = ["tokio02_crate", "async-trait", "futures-io", "futures-util"]
-tokio02-native-tls = ["tokio02", "native-tls", "tokio02_native_tls_crate"]
-tokio02-rustls-tls = ["tokio02", "rustls-tls", "tokio02_rustls"]
-tokio1 = ["tokio1_crate", "async-trait", "futures-io", "futures-util"]
-tokio1-native-tls = ["tokio1", "native-tls", "tokio1_native_tls_crate"]
-tokio1-rustls-tls = ["tokio1", "rustls-tls", "tokio1_rustls"]
+async-std1 = ["dep:async-std", "dep:async-trait", "dep:futures-io", "dep:futures-util"]
+async-std1-rustls = ["async-std1", "rustls", "dep:futures-rustls"]
+# deprecated
+async-std1-rustls-tls = ["async-std1-rustls", "rustls-tls"]
+tokio1 = ["dep:tokio1_crate", "dep:async-trait", "dep:futures-io", "dep:futures-util"]
+tokio1-native-tls = ["tokio1", "native-tls", "dep:tokio1_native_tls_crate"]
+tokio1-rustls = ["tokio1", "rustls", "dep:tokio1_rustls"]
+# deprecated
+tokio1-rustls-tls = ["tokio1-rustls", "rustls-tls"]
+tokio1-boring-tls = ["tokio1", "boring-tls", "dep:tokio1_boring"]
+
+dkim = ["dep:base64", "dep:sha2", "dep:rsa", "dep:ed25519-dalek"]
+
+# wasm support
+web = ["dep:web-time"]
+
+[lints.rust]
+unexpected_cfgs = { level = "warn", check-cfg = ['cfg(lettre_ignore_tls_mismatch)'] }
 
 [package.metadata.docs.rs]
 all-features = true
-rustdoc-args = ["--cfg", "docsrs"]
+rustdoc-args = ["--cfg", "docsrs", "--cfg", "lettre_ignore_tls_mismatch"]
+
+[[example]]
+name = "autoconfigure"
+required-features = ["smtp-transport", "native-tls"]
 
 [[example]]
 name = "basic_html"
@@ -130,14 +171,6 @@ required-features = ["smtp-transport", "native-tls", "builder"]
 name = "smtp_selfsigned"
 required-features = ["smtp-transport", "native-tls", "builder"]
 
-[[example]]
-name = "tokio02_smtp_tls"
-required-features = ["smtp-transport", "tokio02", "tokio02-native-tls", "builder"]
-
-[[example]]
-name = "tokio02_smtp_starttls"
-required-features = ["smtp-transport", "tokio02", "tokio02-native-tls", "builder"]
-
 [[example]]
 name = "tokio1_smtp_tls"
 required-features = ["smtp-transport", "tokio1", "tokio1-native-tls", "builder"]

LICENSE

@@ -1,5 +1,5 @@
-Copyright (c) 2014-2020 Alexis Mousset <contact@amousset.me>
-Copyright (c) 2019-2020 Paolo Barbolini <paolo@paolo565.org>
+Copyright (c) 2014-2024 Alexis Mousset <contact@amousset.me>
+Copyright (c) 2019-2025 Paolo Barbolini <paolo@paolo565.org>
 Copyright (c) 2018 K. <kayo@illumium.org>
 
 Permission is hereby granted, free of charge, to any

README.md

@@ -28,22 +28,14 @@
 </div>
 
 <div align="center">
-  <a href="https://deps.rs/crate/lettre/0.10.0-alpha.4">
-    <img src="https://deps.rs/crate/lettre/0.10.0-alpha.4/status.svg"
+  <a href="https://deps.rs/crate/lettre/0.11.15">
+    <img src="https://deps.rs/crate/lettre/0.11.15/status.svg"
       alt="dependency status" />
   </a>
 </div>
 
 ---
 
-**NOTE**: this readme refers to the 0.10 version of lettre, which is
-still being worked on. The master branch and the alpha releases will see
-API breaking changes and some features may be missing or incomplete until
-the stable 0.10.0 release is out.
-Use the [`v0.9.x`](https://github.com/lettre/lettre/tree/v0.9.x) branch for stable releases.
-
----
-
 ## Features
 
 Lettre provides the following features:
@@ -58,50 +50,79 @@ Lettre does not provide (for now):
 
 * Email parsing
 
+## Supported Rust Versions
+
+Lettre supports all Rust versions released in the last 6 months. At the time of writing
+the minimum supported Rust version is 1.74, but this could change at any time either from
+one of our dependencies bumping their MSRV or by a new patch release of lettre.
+
 ## Example
 
-This library requires Rust 1.45 or newer.
+This library requires Rust 1.74 or newer.
 To use this library, add the following to your `Cargo.toml`:
 
-
 ```toml
 [dependencies]
-lettre = "0.10.0-alpha.4"
+lettre = "0.11"
 ```
 
 ```rust,no_run
+use lettre::message::header::ContentType;
 use lettre::transport::smtp::authentication::Credentials;
 use lettre::{Message, SmtpTransport, Transport};
 
-let email = Message::builder()
-    .from("NoBody <nobody@domain.tld>".parse().unwrap())
-    .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
-    .to("Hei <hei@domain.tld>".parse().unwrap())
-    .subject("Happy new year")
-    .body("Be happy!")
-    .unwrap();
+fn main() {
+    let email = Message::builder()
+        .from("NoBody <nobody@domain.tld>".parse().unwrap())
+        .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
+        .to("Hei <hei@domain.tld>".parse().unwrap())
+        .subject("Happy new year")
+        .header(ContentType::TEXT_PLAIN)
+        .body(String::from("Be happy!"))
+        .unwrap();
 
-let creds = Credentials::new("smtp_username".to_string(), "smtp_password".to_string());
+    let creds = Credentials::new("smtp_username".to_owned(), "smtp_password".to_owned());
 
-// Open a remote connection to gmail
-let mailer = SmtpTransport::relay("smtp.gmail.com")
-    .unwrap()
-    .credentials(creds)
-    .build();
+    // Open a remote connection to gmail
+    let mailer = SmtpTransport::relay("smtp.gmail.com")
+        .unwrap()
+        .credentials(creds)
+        .build();
 
-// Send the email
-match mailer.send(&email) {
-    Ok(_) => println!("Email sent successfully!"),
-    Err(e) => panic!("Could not send email: {:?}", e),
+    // Send the email
+    match mailer.send(&email) {
+        Ok(_) => println!("Email sent successfully!"),
+        Err(e) => panic!("Could not send email: {e:?}"),
+    }
 }
 ```
 
+## Not sure of which connect options to use?
+
+Clone the lettre git repository and run the following command (replacing `SMTP_HOST` with your SMTP server's hostname)
+
+```shell
+cargo run --example autoconfigure SMTP_HOST
+```
+
 ## Testing
 
-The `lettre` tests require an open mail server listening locally on port 2525 and the `sendmail` command.
+The `lettre` tests require an open mail server listening locally on port 2525 and the `sendmail` command. If you have python installed
+such a server can be launched with `python -m smtpd -n -c DebuggingServer 127.0.0.1:2525`
 
 Alternatively only unit tests can be run by doing `cargo test --lib`.
 
+## Troubleshooting
+
+These are general steps to be followed when troubleshooting SMTP related issues.
+
+- Ensure basic connectivity, ensure requisite ports are open and daemons are listening.
+- Confirm that your service provider allows traffic on the ports being used for mail transfer.
+- Check SMTP relay authentication and configuration.
+- Validate your DNS records. (DMARC, SPF, DKIM, MX)
+- Verify your SSL/TLS certificates are setup properly.
+- Investigate if filtering, formatting, or filesize limits are causing messages to be lost, delayed, or blocked by relays or remote hosts.
+
 ## Code of conduct
 
 Anyone who interacts with Lettre in any space, including but not limited to

SECURITY.md

@@ -2,7 +2,7 @@
 
 The lettre project team welcomes security reports and is committed to providing prompt attention to security issues.
 Security issues should be reported privately via [security@lettre.rs](mailto:security@lettre.rs). Security issues
-should not be reported via the public Github Issue tracker.
+should not be reported via the public GitHub Issue tracker.
 
 ## Security advisories
 

benches/mailbox_parsing.rs

@@ -0,0 +1,27 @@
+use criterion::{black_box, criterion_group, criterion_main, Criterion};
+use lettre::message::{Mailbox, Mailboxes};
+
+fn bench_parse_single(mailbox: &str) {
+    assert!(mailbox.parse::<Mailbox>().is_ok());
+}
+
+fn bench_parse_multiple(mailboxes: &str) {
+    assert!(mailboxes.parse::<Mailboxes>().is_ok());
+}
+
+fn criterion_benchmark(c: &mut Criterion) {
+    c.bench_function("parse single mailbox", |b| {
+        b.iter(|| bench_parse_single(black_box("\"Benchmark test\" <test@mail.local>")))
+    });
+
+    c.bench_function("parse multiple mailboxes", |b| {
+        b.iter(|| {
+            bench_parse_multiple(black_box(
+                "\"Benchmark test\" <test@mail.local>, Test <test@mail.local>, <test@mail.local>, test@mail.local",
+            ))
+        })
+    });
+}
+
+criterion_group!(benches, criterion_benchmark);
+criterion_main!(benches);

benches/transport_smtp.rs

@@ -1,5 +1,5 @@
 use criterion::{black_box, criterion_group, criterion_main, Criterion};
-use lettre::{Message, SmtpTransport, Transport};
+use lettre::{message::header::ContentType, Message, SmtpTransport, Transport};
 
 fn bench_simple_send(c: &mut Criterion) {
     let sender = SmtpTransport::builder_dangerous("127.0.0.1")
@@ -13,6 +13,7 @@ fn bench_simple_send(c: &mut Criterion) {
                 .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
                 .to("Hei <hei@domain.tld>".parse().unwrap())
                 .subject("Happy new year")
+                .header(ContentType::TEXT_PLAIN)
                 .body(String::from("Be happy!"))
                 .unwrap();
             let result = black_box(sender.send(&email));
@@ -32,6 +33,7 @@ fn bench_reuse_send(c: &mut Criterion) {
                 .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
                 .to("Hei <hei@domain.tld>".parse().unwrap())
                 .subject("Happy new year")
+                .header(ContentType::TEXT_PLAIN)
                 .body(String::from("Be happy!"))
                 .unwrap();
             let result = black_box(sender.send(&email));

clippy.toml

@@ -0,0 +1,3 @@
+disallowed-methods = [
+    { "path" = "std::time::SystemTime::now", reason = "does not work on WASM environments", replacement = "crate::time::now" }
+]

examples/README.md

@@ -14,7 +14,7 @@ This folder contains examples showing how to use lettre in your own projects.
 - [smtp_starttls.rs] - Send an email over SMTP with STARTTLS and authenticating with username and password.
 - [smtp_selfsigned.rs] - Send an email over SMTP encrypted with TLS using a self-signed certificate and authenticating with username and password.
 - The [smtp_tls.rs] and [smtp_starttls.rs] examples also feature `async`hronous implementations powered by [Tokio](https://tokio.rs/).
-  These files are prefixed with `tokio02_`, `tokio1_` or `asyncstd1_`.
+  These files are prefixed with `tokio1_` or `asyncstd1_`.
 
 [basic_html.rs]: ./basic_html.rs
 [maud_html.rs]: ./maud_html.rs

examples/asyncstd1_smtp_starttls.rs

@@ -1,6 +1,6 @@
 use lettre::{
-    transport::smtp::authentication::Credentials, AsyncSmtpTransport, AsyncStd1Connector,
-    AsyncStd1Transport, Message,
+    message::header::ContentType, transport::smtp::authentication::Credentials, AsyncSmtpTransport,
+    AsyncStd1Executor, AsyncTransport, Message,
 };
 
 #[async_std::main]
@@ -12,20 +12,22 @@ async fn main() {
         .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
         .to("Hei <hei@domain.tld>".parse().unwrap())
         .subject("Happy new async year")
+        .header(ContentType::TEXT_PLAIN)
         .body(String::from("Be happy with async!"))
         .unwrap();
 
-    let creds = Credentials::new("smtp_username".to_string(), "smtp_password".to_string());
+    let creds = Credentials::new("smtp_username".to_owned(), "smtp_password".to_owned());
 
     // Open a remote connection to gmail using STARTTLS
-    let mailer = AsyncSmtpTransport::<AsyncStd1Connector>::starttls_relay("smtp.gmail.com")
-        .unwrap()
-        .credentials(creds)
-        .build();
+    let mailer: AsyncSmtpTransport<AsyncStd1Executor> =
+        AsyncSmtpTransport::<AsyncStd1Executor>::starttls_relay("smtp.gmail.com")
+            .unwrap()
+            .credentials(creds)
+            .build();
 
     // Send the email
     match mailer.send(email).await {
         Ok(_) => println!("Email sent successfully!"),
-        Err(e) => panic!("Could not send email: {:?}", e),
+        Err(e) => panic!("Could not send email: {e:?}"),
     }
 }

examples/asyncstd1_smtp_tls.rs

@@ -1,6 +1,6 @@
 use lettre::{
-    transport::smtp::authentication::Credentials, AsyncSmtpTransport, AsyncStd1Connector,
-    AsyncStd1Transport, Message,
+    message::header::ContentType, transport::smtp::authentication::Credentials, AsyncSmtpTransport,
+    AsyncStd1Executor, AsyncTransport, Message,
 };
 
 #[async_std::main]
@@ -12,20 +12,22 @@ async fn main() {
         .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
         .to("Hei <hei@domain.tld>".parse().unwrap())
         .subject("Happy new async year")
+        .header(ContentType::TEXT_PLAIN)
         .body(String::from("Be happy with async!"))
         .unwrap();
 
-    let creds = Credentials::new("smtp_username".to_string(), "smtp_password".to_string());
+    let creds = Credentials::new("smtp_username".to_owned(), "smtp_password".to_owned());
 
     // Open a remote connection to gmail
-    let mailer = AsyncSmtpTransport::<AsyncStd1Connector>::relay("smtp.gmail.com")
-        .unwrap()
-        .credentials(creds)
-        .build();
+    let mailer: AsyncSmtpTransport<AsyncStd1Executor> =
+        AsyncSmtpTransport::<AsyncStd1Executor>::relay("smtp.gmail.com")
+            .unwrap()
+            .credentials(creds)
+            .build();
 
     // Send the email
     match mailer.send(email).await {
         Ok(_) => println!("Email sent successfully!"),
-        Err(e) => panic!("Could not send email: {:?}", e),
+        Err(e) => panic!("Could not send email: {e:?}"),
     }
 }

examples/autoconfigure.rs

@@ -0,0 +1,93 @@
+use std::{env, process, time::Duration};
+
+use lettre::SmtpTransport;
+
+fn main() {
+    tracing_subscriber::fmt::init();
+
+    let smtp_host = match env::args().nth(1) {
+        Some(smtp_host) => smtp_host,
+        None => {
+            println!("Please provide the SMTP host as the first argument to this command");
+            process::exit(1);
+        }
+    };
+
+    // TLS wrapped connection
+    {
+        tracing::info!(
+            "Trying to establish a TLS wrapped connection to {}",
+            smtp_host
+        );
+
+        let transport = SmtpTransport::relay(&smtp_host)
+            .expect("build SmtpTransport::relay")
+            .timeout(Some(Duration::from_secs(10)))
+            .build();
+        match transport.test_connection() {
+            Ok(true) => {
+                tracing::info!("Successfully connected to {} via a TLS wrapped connection (SmtpTransport::relay). This is the fastest option available for connecting to an SMTP server", smtp_host);
+            }
+            Ok(false) => {
+                tracing::error!("Couldn't connect to {} via a TLS wrapped connection. No more information is available", smtp_host);
+            }
+            Err(err) => {
+                tracing::error!(err = %err, "Couldn't connect to {} via a TLS wrapped connection", smtp_host);
+            }
+        }
+    }
+
+    println!();
+
+    // Plaintext connection which MUST then successfully upgrade to TLS via STARTTLS
+    {
+        tracing::info!("Trying to establish a plaintext connection to {} and then upgrading it via the SMTP STARTTLS extension", smtp_host);
+
+        let transport = SmtpTransport::starttls_relay(&smtp_host)
+            .expect("build SmtpTransport::starttls_relay")
+            .timeout(Some(Duration::from_secs(10)))
+            .build();
+        match transport.test_connection() {
+            Ok(true) => {
+                tracing::info!("Successfully connected to {} via a plaintext connection which then got upgraded to TLS via the SMTP STARTTLS extension (SmtpTransport::starttls_relay). This is the second best option after the previous TLS wrapped option", smtp_host);
+            }
+            Ok(false) => {
+                tracing::error!(
+                    "Couldn't connect to {} via STARTTLS. No more information is available",
+                    smtp_host
+                );
+            }
+            Err(err) => {
+                tracing::error!(err = %err, "Couldn't connect to {} via STARTTLS", smtp_host);
+            }
+        }
+    }
+
+    println!();
+
+    // Plaintext connection (very insecure)
+    {
+        tracing::info!(
+            "Trying to establish a plaintext connection to {}",
+            smtp_host
+        );
+
+        let transport = SmtpTransport::builder_dangerous(&smtp_host)
+            .timeout(Some(Duration::from_secs(10)))
+            .build();
+        match transport.test_connection() {
+            Ok(true) => {
+                tracing::info!("Successfully connected to {} via a plaintext connection. This option is very insecure and shouldn't be used on the public internet (SmtpTransport::builder_dangerous)", smtp_host);
+            }
+            Ok(false) => {
+                tracing::error!(
+                    "Couldn't connect to {} via a plaintext connection. No more information is available",
+                    smtp_host
+                );
+            }
+            Err(err) => {
+                tracing::error!(err = %err, "Couldn't connect to {} via a plaintext connection", smtp_host);
+            }
+        }
+    }
+}

examples/basic_html.rs

@@ -1,5 +1,7 @@
-use lettre::message::{header, MultiPart, SinglePart};
-use lettre::{FileTransport, Message, Transport};
+use lettre::{
+    message::{header, MultiPart, SinglePart},
+    FileTransport, Message, Transport,
+};
 
 fn main() {
     // The html we want to send.
@@ -27,16 +29,12 @@ fn main() {
             MultiPart::alternative() // This is composed of two parts.
                 .singlepart(
                     SinglePart::builder()
-                        .header(header::ContentType(
-                            "text/plain; charset=utf8".parse().unwrap(),
-                        ))
+                        .header(header::ContentType::TEXT_PLAIN)
                         .body(String::from("Hello from Lettre! A mailer library for Rust")), // Every message should have a plain text fallback.
                 )
                 .singlepart(
                     SinglePart::builder()
-                        .header(header::ContentType(
-                            "text/html; charset=utf8".parse().unwrap(),
-                        ))
+                        .header(header::ContentType::TEXT_HTML)
                         .body(String::from(html)),
                 ),
         )

examples/maud_html.rs

@@ -1,5 +1,7 @@
-use lettre::message::{header, MultiPart, SinglePart};
-use lettre::{FileTransport, Message, Transport};
+use lettre::{
+    message::{header, MultiPart, SinglePart},
+    FileTransport, Message, Transport,
+};
 use maud::html;
 
 fn main() {
@@ -36,16 +38,12 @@ fn main() {
             MultiPart::alternative() // This is composed of two parts.
                 .singlepart(
                     SinglePart::builder()
-                        .header(header::ContentType(
-                            "text/plain; charset=utf8".parse().unwrap(),
-                        ))
+                        .header(header::ContentType::TEXT_PLAIN)
                         .body(String::from("Hello from Lettre! A mailer library for Rust")), // Every message should have a plain text fallback.
                 )
                 .singlepart(
                     SinglePart::builder()
-                        .header(header::ContentType(
-                            "text/html; charset=utf8".parse().unwrap(),
-                        ))
+                        .header(header::ContentType::TEXT_HTML)
                         .body(html.into_string()),
                 ),
         )

examples/smtp.rs

@@ -1,4 +1,4 @@
-use lettre::{Message, SmtpTransport, Transport};
+use lettre::{message::header::ContentType, Message, SmtpTransport, Transport};
 
 fn main() {
     tracing_subscriber::fmt::init();
@@ -8,6 +8,7 @@ fn main() {
         .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
         .to("Hei <hei@domain.tld>".parse().unwrap())
         .subject("Happy new year")
+        .header(ContentType::TEXT_PLAIN)
         .body(String::from("Be happy!"))
         .unwrap();
 
@@ -17,6 +18,6 @@ fn main() {
     // Send the email
     match mailer.send(&email) {
         Ok(_) => println!("Email sent successfully!"),
-        Err(e) => panic!("Could not send email: {:?}", e),
+        Err(e) => panic!("Could not send email: {e:?}"),
     }
 }

examples/smtp_selfsigned.rs

@@ -1,8 +1,11 @@
 use std::fs;
 
 use lettre::{
-    transport::smtp::authentication::Credentials,
-    transport::smtp::client::{Certificate, Tls, TlsParameters},
+    message::header::ContentType,
+    transport::smtp::{
+        authentication::Credentials,
+        client::{Certificate, Tls, TlsParameters},
+    },
     Message, SmtpTransport, Transport,
 };
 
@@ -14,17 +17,19 @@ fn main() {
         .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
         .to("Hei <hei@domain.tld>".parse().unwrap())
         .subject("Happy new year")
+        .header(ContentType::TEXT_PLAIN)
         .body(String::from("Be happy!"))
         .unwrap();
 
     // Use a custom certificate stored on disk to securely verify the server's certificate
     let pem_cert = fs::read("certificate.pem").unwrap();
     let cert = Certificate::from_pem(&pem_cert).unwrap();
-    let mut tls = TlsParameters::builder("smtp.server.com".to_string());
-    tls.add_root_certificate(cert);
-    let tls = tls.build().unwrap();
+    let tls = TlsParameters::builder("smtp.server.com".to_owned())
+        .add_root_certificate(cert)
+        .build()
+        .unwrap();
 
-    let creds = Credentials::new("smtp_username".to_string(), "smtp_password".to_string());
+    let creds = Credentials::new("smtp_username".to_owned(), "smtp_password".to_owned());
 
     // Open a remote connection to the smtp server
     let mailer = SmtpTransport::builder_dangerous("smtp.server.com")
@@ -36,6 +41,6 @@ fn main() {
     // Send the email
     match mailer.send(&email) {
         Ok(_) => println!("Email sent successfully!"),
-        Err(e) => panic!("Could not send email: {:?}", e),
+        Err(e) => panic!("Could not send email: {e:?}"),
     }
 }

examples/smtp_starttls.rs

@@ -1,4 +1,7 @@
-use lettre::{transport::smtp::authentication::Credentials, Message, SmtpTransport, Transport};
+use lettre::{
+    message::header::ContentType, transport::smtp::authentication::Credentials, Message,
+    SmtpTransport, Transport,
+};
 
 fn main() {
     tracing_subscriber::fmt::init();
@@ -8,10 +11,11 @@ fn main() {
         .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
         .to("Hei <hei@domain.tld>".parse().unwrap())
         .subject("Happy new year")
+        .header(ContentType::TEXT_PLAIN)
         .body(String::from("Be happy!"))
         .unwrap();
 
-    let creds = Credentials::new("smtp_username".to_string(), "smtp_password".to_string());
+    let creds = Credentials::new("smtp_username".to_owned(), "smtp_password".to_owned());
 
     // Open a remote connection to gmail using STARTTLS
     let mailer = SmtpTransport::starttls_relay("smtp.gmail.com")
@@ -22,6 +26,6 @@ fn main() {
     // Send the email
     match mailer.send(&email) {
         Ok(_) => println!("Email sent successfully!"),
-        Err(e) => panic!("Could not send email: {:?}", e),
+        Err(e) => panic!("Could not send email: {e:?}"),
     }
 }

examples/smtp_tls.rs

@@ -1,4 +1,7 @@
-use lettre::{transport::smtp::authentication::Credentials, Message, SmtpTransport, Transport};
+use lettre::{
+    message::header::ContentType, transport::smtp::authentication::Credentials, Message,
+    SmtpTransport, Transport,
+};
 
 fn main() {
     tracing_subscriber::fmt::init();
@@ -8,10 +11,11 @@ fn main() {
         .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
         .to("Hei <hei@domain.tld>".parse().unwrap())
         .subject("Happy new year")
+        .header(ContentType::TEXT_PLAIN)
         .body(String::from("Be happy!"))
         .unwrap();
 
-    let creds = Credentials::new("smtp_username".to_string(), "smtp_password".to_string());
+    let creds = Credentials::new("smtp_username".to_owned(), "smtp_password".to_owned());
 
     // Open a remote connection to gmail
     let mailer = SmtpTransport::relay("smtp.gmail.com")
@@ -22,6 +26,6 @@ fn main() {
     // Send the email
     match mailer.send(&email) {
         Ok(_) => println!("Email sent successfully!"),
-        Err(e) => panic!("Could not send email: {:?}", e),
+        Err(e) => panic!("Could not send email: {e:?}"),
     }
 }

examples/tokio02_smtp_starttls.rs

@@ -1,36 +0,0 @@
-// This line is only to make it compile from lettre's examples folder,
-// since it uses Rust 2018 crate renaming to import tokio.
-// Won't be needed in user's code.
-use tokio02_crate as tokio;
-
-use lettre::{
-    transport::smtp::authentication::Credentials, AsyncSmtpTransport, Message, Tokio02Connector,
-    Tokio02Transport,
-};
-
-#[tokio::main]
-async fn main() {
-    tracing_subscriber::fmt::init();
-
-    let email = Message::builder()
-        .from("NoBody <nobody@domain.tld>".parse().unwrap())
-        .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
-        .to("Hei <hei@domain.tld>".parse().unwrap())
-        .subject("Happy new async year")
-        .body(String::from("Be happy with async!"))
-        .unwrap();
-
-    let creds = Credentials::new("smtp_username".to_string(), "smtp_password".to_string());
-
-    // Open a remote connection to gmail using STARTTLS
-    let mailer = AsyncSmtpTransport::<Tokio02Connector>::starttls_relay("smtp.gmail.com")
-        .unwrap()
-        .credentials(creds)
-        .build();
-
-    // Send the email
-    match mailer.send(email).await {
-        Ok(_) => println!("Email sent successfully!"),
-        Err(e) => panic!("Could not send email: {:?}", e),
-    }
-}

examples/tokio02_smtp_tls.rs

@@ -1,36 +0,0 @@
-// This line is only to make it compile from lettre's examples folder,
-// since it uses Rust 2018 crate renaming to import tokio.
-// Won't be needed in user's code.
-use tokio02_crate as tokio;
-
-use lettre::{
-    transport::smtp::authentication::Credentials, AsyncSmtpTransport, Message, Tokio02Connector,
-    Tokio02Transport,
-};
-
-#[tokio::main]
-async fn main() {
-    tracing_subscriber::fmt::init();
-
-    let email = Message::builder()
-        .from("NoBody <nobody@domain.tld>".parse().unwrap())
-        .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
-        .to("Hei <hei@domain.tld>".parse().unwrap())
-        .subject("Happy new async year")
-        .body(String::from("Be happy with async!"))
-        .unwrap();
-
-    let creds = Credentials::new("smtp_username".to_string(), "smtp_password".to_string());
-
-    // Open a remote connection to gmail
-    let mailer = AsyncSmtpTransport::<Tokio02Connector>::relay("smtp.gmail.com")
-        .unwrap()
-        .credentials(creds)
-        .build();
-
-    // Send the email
-    match mailer.send(email).await {
-        Ok(_) => println!("Email sent successfully!"),
-        Err(e) => panic!("Could not send email: {:?}", e),
-    }
-}

examples/tokio1_smtp_starttls.rs

@@ -1,12 +1,11 @@
 // This line is only to make it compile from lettre's examples folder,
 // since it uses Rust 2018 crate renaming to import tokio.
 // Won't be needed in user's code.
-use tokio1_crate as tokio;
-
 use lettre::{
-    transport::smtp::authentication::Credentials, AsyncSmtpTransport, Message, Tokio1Connector,
-    Tokio1Transport,
+    message::header::ContentType, transport::smtp::authentication::Credentials, AsyncSmtpTransport,
+    AsyncTransport, Message, Tokio1Executor,
 };
+use tokio1_crate as tokio;
 
 #[tokio::main]
 async fn main() {
@@ -17,20 +16,22 @@ async fn main() {
         .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
         .to("Hei <hei@domain.tld>".parse().unwrap())
         .subject("Happy new async year")
+        .header(ContentType::TEXT_PLAIN)
         .body(String::from("Be happy with async!"))
         .unwrap();
 
-    let creds = Credentials::new("smtp_username".to_string(), "smtp_password".to_string());
+    let creds = Credentials::new("smtp_username".to_owned(), "smtp_password".to_owned());
 
     // Open a remote connection to gmail using STARTTLS
-    let mailer = AsyncSmtpTransport::<Tokio1Connector>::starttls_relay("smtp.gmail.com")
-        .unwrap()
-        .credentials(creds)
-        .build();
+    let mailer: AsyncSmtpTransport<Tokio1Executor> =
+        AsyncSmtpTransport::<Tokio1Executor>::starttls_relay("smtp.gmail.com")
+            .unwrap()
+            .credentials(creds)
+            .build();
 
     // Send the email
     match mailer.send(email).await {
         Ok(_) => println!("Email sent successfully!"),
-        Err(e) => panic!("Could not send email: {:?}", e),
+        Err(e) => panic!("Could not send email: {e:?}"),
     }
 }

examples/tokio1_smtp_tls.rs

@@ -1,12 +1,11 @@
 // This line is only to make it compile from lettre's examples folder,
 // since it uses Rust 2018 crate renaming to import tokio.
 // Won't be needed in user's code.
-use tokio1_crate as tokio;
-
 use lettre::{
-    transport::smtp::authentication::Credentials, AsyncSmtpTransport, Message, Tokio1Connector,
-    Tokio1Transport,
+    message::header::ContentType, transport::smtp::authentication::Credentials, AsyncSmtpTransport,
+    AsyncTransport, Message, Tokio1Executor,
 };
+use tokio1_crate as tokio;
 
 #[tokio::main]
 async fn main() {
@@ -17,20 +16,22 @@ async fn main() {
         .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
         .to("Hei <hei@domain.tld>".parse().unwrap())
         .subject("Happy new async year")
+        .header(ContentType::TEXT_PLAIN)
         .body(String::from("Be happy with async!"))
         .unwrap();
 
-    let creds = Credentials::new("smtp_username".to_string(), "smtp_password".to_string());
+    let creds = Credentials::new("smtp_username".to_owned(), "smtp_password".to_owned());
 
     // Open a remote connection to gmail
-    let mailer = AsyncSmtpTransport::<Tokio1Connector>::relay("smtp.gmail.com")
-        .unwrap()
-        .credentials(creds)
-        .build();
+    let mailer: AsyncSmtpTransport<Tokio1Executor> =
+        AsyncSmtpTransport::<Tokio1Executor>::relay("smtp.gmail.com")
+            .unwrap()
+            .credentials(creds)
+            .build();
 
     // Send the email
     match mailer.send(email).await {
         Ok(_) => println!("Email sent successfully!"),
-        Err(e) => panic!("Could not send email: {:?}", e),
+        Err(e) => panic!("Could not send email: {e:?}"),
     }
 }

rustfmt.toml

@@ -0,0 +1,3 @@
+format_code_in_doc_comments = true
+imports_granularity = "Crate"
+group_imports = "StdExternalCrate"

src/address/envelope.rs

@@ -1,6 +1,3 @@
-#[cfg(feature = "builder")]
-use std::convert::TryFrom;
-
 use super::Address;
 #[cfg(feature = "builder")]
 use crate::message::header::{self, Headers};
@@ -17,25 +14,82 @@ pub struct Envelope {
     /// The envelope recipient's addresses
     ///
     /// This can not be empty.
+    #[cfg_attr(
+        feature = "serde",
+        serde(deserialize_with = "serde_forward_path::deserialize")
+    )]
     forward_path: Vec<Address>,
     /// The envelope sender address
     reverse_path: Option<Address>,
 }
 
+/// just like the default implementation to deserialize `Vec<Address>` but it
+/// forbids **de**serializing empty lists
+#[cfg(feature = "serde")]
+mod serde_forward_path {
+    use super::Address;
+    /// dummy type required for serde
+    /// see example: <https://serde.rs/deserialize-map.html>
+    struct CustomVisitor;
+    impl<'de> serde::de::Visitor<'de> for CustomVisitor {
+        type Value = Vec<Address>;
+
+        fn expecting(&self, formatter: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
+            formatter.write_str("a non-empty list of recipient addresses")
+        }
+
+        fn visit_seq<S>(self, mut access: S) -> Result<Self::Value, S::Error>
+        where
+            S: serde::de::SeqAccess<'de>,
+        {
+            let mut seq: Vec<Address> = Vec::with_capacity(access.size_hint().unwrap_or(0));
+            while let Some(key) = access.next_element()? {
+                seq.push(key);
+            }
+            if seq.is_empty() {
+                Err(serde::de::Error::invalid_length(seq.len(), &self))
+            } else {
+                Ok(seq)
+            }
+        }
+    }
+    pub(super) fn deserialize<'de, D>(deserializer: D) -> Result<Vec<Address>, D::Error>
+    where
+        D: serde::Deserializer<'de>,
+    {
+        deserializer.deserialize_seq(CustomVisitor {})
+    }
+
+    #[cfg(test)]
+    mod tests {
+        #[test]
+        fn deserializing_empty_recipient_list_returns_error() {
+            assert!(
+                serde_json::from_str::<crate::address::Envelope>(r#"{"forward_path": []}"#)
+                    .is_err()
+            );
+        }
+        #[test]
+        fn deserializing_non_empty_recipient_list_is_ok() {
+            serde_json::from_str::<crate::address::Envelope>(
+                r#"{ "forward_path": [ {"user":"foo", "domain":"example.com"} ] }"#,
+            )
+            .unwrap();
+        }
+    }
+}
+
 impl Envelope {
     /// Creates a new envelope, which may fail if `to` is empty.
     ///
     /// # Examples
     ///
-    /// ```
-    /// use std::str::FromStr;
-    /// # use lettre::Address;
-    /// # use lettre::address::Envelope;
-    ///
+    /// ```rust
+    /// # use lettre::address::{Address, Envelope};
     /// # use std::error::Error;
     /// # fn main() -> Result<(), Box<dyn Error>> {
-    /// let sender = Address::from_str("from@email.com")?;
-    /// let recipients = vec![Address::from_str("to@email.com")?];
+    /// let sender = "sender@email.com".parse::<Address>()?;
+    /// let recipients = vec!["to@email.com".parse::<Address>()?];
     ///
     /// let envelope = Envelope::new(Some(sender), recipients);
     /// # Ok(())
@@ -59,15 +113,12 @@ impl Envelope {
     ///
     /// # Examples
     ///
-    /// ```
-    /// use std::str::FromStr;
-    /// # use lettre::Address;
-    /// # use lettre::address::Envelope;
-    ///
+    /// ```rust
+    /// # use lettre::address::{Address, Envelope};
     /// # use std::error::Error;
     /// # fn main() -> Result<(), Box<dyn Error>> {
-    /// let sender = Address::from_str("from@email.com")?;
-    /// let recipients = vec![Address::from_str("to@email.com")?];
+    /// let sender = "from@email.com".parse::<Address>()?;
+    /// let recipients = vec!["to@email.com".parse::<Address>()?];
     ///
     /// let envelope = Envelope::new(Some(sender), recipients.clone())?;
     /// assert_eq!(envelope.to(), recipients.as_slice());
@@ -82,15 +133,12 @@ impl Envelope {
     ///
     /// # Examples
     ///
-    /// ```
-    /// use std::str::FromStr;
-    /// # use lettre::Address;
-    /// # use lettre::address::Envelope;
-    ///
+    /// ```rust
+    /// # use lettre::address::{Address, Envelope};
     /// # use std::error::Error;
     /// # fn main() -> Result<(), Box<dyn Error>> {
-    /// let sender = Address::from_str("from@email.com")?;
-    /// let recipients = vec![Address::from_str("to@email.com")?];
+    /// let sender = "from@email.com".parse::<Address>()?;
+    /// let recipients = vec!["to@email.com".parse::<Address>()?];
     ///
     /// let envelope = Envelope::new(Some(sender), recipients.clone())?;
     /// assert!(envelope.from().is_some());
@@ -103,6 +151,15 @@ impl Envelope {
     pub fn from(&self) -> Option<&Address> {
         self.reverse_path.as_ref()
     }
+
+    #[cfg(feature = "smtp-transport")]
+    /// Check if any of the addresses in the envelope contains non-ascii chars
+    pub(crate) fn has_non_ascii_addresses(&self) -> bool {
+        self.reverse_path
+            .iter()
+            .chain(self.forward_path.iter())
+            .any(|a| !a.is_ascii())
+    }
 }
 
 #[cfg(feature = "builder")]
@@ -112,15 +169,16 @@ impl TryFrom<&Headers> for Envelope {
     fn try_from(headers: &Headers) -> Result<Self, Self::Error> {
         let from = match headers.get::<header::Sender>() {
             // If there is a Sender, use it
-            Some(header::Sender(a)) => Some(a.email.clone()),
+            Some(sender) => Some(Mailbox::from(sender).email),
             // ... else try From
             None => match headers.get::<header::From>() {
                 Some(header::From(a)) => {
-                    let from: Vec<Mailbox> = a.clone().into();
+                    let mut from: Vec<Mailbox> = a.into();
                     if from.len() > 1 {
                         return Err(Error::TooManyFrom);
                     }
-                    Some(from[0].email.clone())
+                    let from = from.pop().expect("From header has 1 Mailbox");
+                    Some(from.email)
                 }
                 None => None,
             },
@@ -128,18 +186,16 @@ impl TryFrom<&Headers> for Envelope {
 
         fn add_addresses_from_mailboxes(
             addresses: &mut Vec<Address>,
-            mailboxes: Option<&Mailboxes>,
+            mailboxes: Option<Mailboxes>,
         ) {
             if let Some(mailboxes) = mailboxes {
-                for mailbox in mailboxes.iter() {
-                    addresses.push(mailbox.email.clone());
-                }
+                addresses.extend(mailboxes.into_iter().map(|mb| mb.email));
             }
         }
         let mut to = vec![];
-        add_addresses_from_mailboxes(&mut to, headers.get::<header::To>().map(|h| &h.0));
-        add_addresses_from_mailboxes(&mut to, headers.get::<header::Cc>().map(|h| &h.0));
-        add_addresses_from_mailboxes(&mut to, headers.get::<header::Bcc>().map(|h| &h.0));
+        add_addresses_from_mailboxes(&mut to, headers.get::<header::To>().map(|h| h.0));
+        add_addresses_from_mailboxes(&mut to, headers.get::<header::Cc>().map(|h| h.0));
+        add_addresses_from_mailboxes(&mut to, headers.get::<header::Bcc>().map(|h| h.0));
 
         Self::new(from, to)
     }

src/address/mod.rs

@@ -1,8 +1,12 @@
+//! Email addresses
+
 #[cfg(feature = "serde")]
 mod serde;
 
 mod envelope;
 mod types;
 
-pub use self::envelope::Envelope;
-pub use self::types::{Address, AddressError};
+pub use self::{
+    envelope::Envelope,
+    types::{Address, AddressError},
+};

src/address/serde.rs

@@ -36,7 +36,7 @@ impl<'de> Deserialize<'de> for Address {
             {
                 struct FieldVisitor;
 
-                impl<'de> Visitor<'de> for FieldVisitor {
+                impl Visitor<'_> for FieldVisitor {
                     type Value = Field;
 
                     fn expecting(&self, formatter: &mut Formatter<'_>) -> FmtResult {

src/address/types.rs

@@ -1,10 +1,6 @@
 //! Representation of an email address
 
-use idna::domain_to_ascii;
-use once_cell::sync::Lazy;
-use regex::Regex;
 use std::{
-    convert::{TryFrom, TryInto},
     error::Error,
     ffi::OsStr,
     fmt::{Display, Formatter, Result as FmtResult},
@@ -12,21 +8,27 @@ use std::{
     str::FromStr,
 };
 
+use email_address::EmailAddress;
+use idna::domain_to_ascii;
+
 /// Represents an email address with a user and a domain name.
 ///
 /// This type contains email in canonical form (_user@domain.tld_).
 ///
-/// **NOTE**: Enable feature "serde" to be able serialize/deserialize it using [serde](https://serde.rs/).
+/// **NOTE**: Enable feature "serde" to be able to serialize/deserialize it using [serde](https://serde.rs/).
 ///
 /// # Examples
 ///
 /// You can create an `Address` from a user and a domain:
 ///
 /// ```
-/// # use lettre::Address;
+/// use lettre::Address;
+///
 /// # use std::error::Error;
 /// # fn main() -> Result<(), Box<dyn Error>> {
-/// let address = Address::new("example", "email.com")?;
+/// let address = Address::new("user", "email.com")?;
+/// assert_eq!(address.user(), "user");
+/// assert_eq!(address.domain(), "email.com");
 /// # Ok(())
 /// # }
 /// ```
@@ -34,11 +36,13 @@ use std::{
 /// You can also create an `Address` from a string literal by parsing it:
 ///
 /// ```
-/// use std::str::FromStr;
-/// # use lettre::Address;
+/// use lettre::Address;
+///
 /// # use std::error::Error;
 /// # fn main() -> Result<(), Box<dyn Error>> {
-/// let address = Address::from_str("example@email.com")?;
+/// let address = "user@email.com".parse::<Address>()?;
+/// assert_eq!(address.user(), "user");
+/// assert_eq!(address.domain(), "email.com");
 /// # Ok(())
 /// # }
 /// ```
@@ -50,42 +54,6 @@ pub struct Address {
     at_start: usize,
 }
 
-impl<U, D> TryFrom<(U, D)> for Address
-where
-    U: AsRef<str>,
-    D: AsRef<str>,
-{
-    type Error = AddressError;
-
-    fn try_from((user, domain): (U, D)) -> Result<Self, Self::Error> {
-        let user = user.as_ref();
-        Address::check_user(user)?;
-
-        let domain = domain.as_ref();
-        Address::check_domain(domain)?;
-
-        let serialized = format!("{}@{}", user, domain);
-        Ok(Address {
-            serialized,
-            at_start: user.len(),
-        })
-    }
-}
-
-// Regex from the specs
-// https://html.spec.whatwg.org/multipage/forms.html#valid-e-mail-address
-// It will mark esoteric email addresses like quoted string as invalid
-static USER_RE: Lazy<Regex> =
-    Lazy::new(|| Regex::new(r"^(?i)[a-z0-9.!#$%&'*+/=?^_`{|}~-]+\z").unwrap());
-static DOMAIN_RE: Lazy<Regex> = Lazy::new(|| {
-    Regex::new(
-        r"(?i)^[a-z0-9](?:[a-z0-9-]{0,61}[a-z0-9])?(?:.[a-z0-9](?:[a-z0-9-]{0,61}[a-z0-9])?)*$",
-    )
-    .unwrap()
-});
-// literal form, ipv4 or ipv6 address (SMTP 4.1.3)
-static LITERAL_RE: Lazy<Regex> = Lazy::new(|| Regex::new(r"(?i)\[([A-f0-9:\.]+)\]\z").unwrap());
-
 impl Address {
     /// Creates a new email address from a user and domain.
     ///
@@ -96,8 +64,8 @@ impl Address {
     ///
     /// # use std::error::Error;
     /// # fn main() -> Result<(), Box<dyn Error>> {
-    /// let address = Address::new("example", "email.com")?;
-    /// let expected: Address = "example@email.com".parse()?;
+    /// let address = Address::new("user", "email.com")?;
+    /// let expected = "user@email.com".parse::<Address>()?;
     /// assert_eq!(expected, address);
     /// # Ok(())
     /// # }
@@ -115,8 +83,8 @@ impl Address {
     ///
     /// # use std::error::Error;
     /// # fn main() -> Result<(), Box<dyn Error>> {
-    /// let address = Address::new("example", "email.com")?;
-    /// assert_eq!("example", address.user());
+    /// let address = Address::new("user", "email.com")?;
+    /// assert_eq!(address.user(), "user");
     /// # Ok(())
     /// # }
     /// ```
@@ -133,8 +101,8 @@ impl Address {
     ///
     /// # use std::error::Error;
     /// # fn main() -> Result<(), Box<dyn Error>> {
-    /// let address = Address::new("example", "email.com")?;
-    /// assert_eq!("email.com", address.domain());
+    /// let address = Address::new("user", "email.com")?;
+    /// assert_eq!(address.domain(), "email.com");
     /// # Ok(())
     /// # }
     /// ```
@@ -143,7 +111,7 @@ impl Address {
     }
 
     pub(super) fn check_user(user: &str) -> Result<(), AddressError> {
-        if USER_RE.is_match(user) {
+        if EmailAddress::is_valid_local_part(user) {
             Ok(())
         } else {
             Err(AddressError::InvalidUser)
@@ -159,20 +127,29 @@ impl Address {
     }
 
     fn check_domain_ascii(domain: &str) -> Result<(), AddressError> {
-        if DOMAIN_RE.is_match(domain) {
+        // Domain
+        if EmailAddress::is_valid_domain(domain) {
             return Ok(());
         }
 
-        if let Some(caps) = LITERAL_RE.captures(domain) {
-            if let Some(cap) = caps.get(1) {
-                if cap.as_str().parse::<IpAddr>().is_ok() {
-                    return Ok(());
-                }
-            }
+        // IP
+        let ip = domain
+            .strip_prefix('[')
+            .and_then(|ip| ip.strip_suffix(']'))
+            .unwrap_or(domain);
+
+        if ip.parse::<IpAddr>().is_ok() {
+            return Ok(());
         }
 
         Err(AddressError::InvalidDomain)
     }
+
+    #[cfg(feature = "smtp-transport")]
+    /// Check if the address contains non-ascii chars
+    pub(super) fn is_ascii(&self) -> bool {
+        self.serialized.is_ascii()
+    }
 }
 
 impl Display for Address {
@@ -185,19 +162,48 @@ impl FromStr for Address {
     type Err = AddressError;
 
     fn from_str(val: &str) -> Result<Self, AddressError> {
-        let mut parts = val.rsplitn(2, '@');
-        let domain = parts.next().ok_or(AddressError::MissingParts)?;
-        let user = parts.next().ok_or(AddressError::MissingParts)?;
-
-        Address::check_user(user)?;
-        Address::check_domain(domain)?;
+        let at_start = check_address(val)?;
         Ok(Address {
             serialized: val.into(),
+            at_start,
+        })
+    }
+}
+
+impl<U, D> TryFrom<(U, D)> for Address
+where
+    U: AsRef<str>,
+    D: AsRef<str>,
+{
+    type Error = AddressError;
+
+    fn try_from((user, domain): (U, D)) -> Result<Self, Self::Error> {
+        let user = user.as_ref();
+        Address::check_user(user)?;
+
+        let domain = domain.as_ref();
+        Address::check_domain(domain)?;
+
+        let serialized = format!("{user}@{domain}");
+        Ok(Address {
+            serialized,
             at_start: user.len(),
         })
     }
 }
 
+impl TryFrom<String> for Address {
+    type Error = AddressError;
+
+    fn try_from(serialized: String) -> Result<Self, AddressError> {
+        let at_start = check_address(&serialized)?;
+        Ok(Address {
+            serialized,
+            at_start,
+        })
+    }
+}
+
 impl AsRef<str> for Address {
     fn as_ref(&self) -> &str {
         &self.serialized
@@ -210,13 +216,30 @@ impl AsRef<OsStr> for Address {
     }
 }
 
-#[derive(Debug, PartialEq, Clone, Copy)]
+fn check_address(val: &str) -> Result<usize, AddressError> {
+    let mut parts = val.rsplitn(2, '@');
+    let domain = parts.next().ok_or(AddressError::MissingParts)?;
+    let user = parts.next().ok_or(AddressError::MissingParts)?;
+
+    Address::check_user(user)?;
+    Address::check_domain(domain)?;
+    Ok(user.len())
+}
+
+#[derive(Debug, PartialEq, Eq, Clone, Copy)]
+#[non_exhaustive]
+/// Errors in email addresses parsing
 pub enum AddressError {
+    /// Missing domain or user
     MissingParts,
+    /// Unbalanced angle bracket
     Unbalanced,
+    /// Invalid email user
     InvalidUser,
+    /// Invalid email domain
     InvalidDomain,
-    InvalidUtf8b,
+    /// Invalid input found
+    InvalidInput,
 }
 
 impl Error for AddressError {}
@@ -228,7 +251,7 @@ impl Display for AddressError {
             AddressError::Unbalanced => f.write_str("Unbalanced angle bracket"),
             AddressError::InvalidUser => f.write_str("Invalid email user"),
             AddressError::InvalidDomain => f.write_str("Invalid email domain"),
-            AddressError::InvalidUtf8b => f.write_str("Invalid UTF8b data"),
+            AddressError::InvalidInput => f.write_str("Invalid input"),
         }
     }
 }
@@ -238,7 +261,7 @@ mod tests {
     use super::*;
 
     #[test]
-    fn parse_address() {
+    fn ascii_address() {
         let addr_str = "something@example.com";
         let addr = Address::from_str(addr_str).unwrap();
         let addr2 = Address::new("something", "example.com").unwrap();
@@ -248,4 +271,36 @@ mod tests {
         assert_eq!(addr2.user(), "something");
         assert_eq!(addr2.domain(), "example.com");
     }
+
+    #[test]
+    fn ascii_address_ipv4() {
+        let addr_str = "something@1.1.1.1";
+        let addr = Address::from_str(addr_str).unwrap();
+        let addr2 = Address::new("something", "1.1.1.1").unwrap();
+        assert_eq!(addr, addr2);
+        assert_eq!(addr.user(), "something");
+        assert_eq!(addr.domain(), "1.1.1.1");
+        assert_eq!(addr2.user(), "something");
+        assert_eq!(addr2.domain(), "1.1.1.1");
+    }
+
+    #[test]
+    fn ascii_address_ipv6() {
+        let addr_str = "something@[2606:4700:4700::1111]";
+        let addr = Address::from_str(addr_str).unwrap();
+        let addr2 = Address::new("something", "[2606:4700:4700::1111]").unwrap();
+        assert_eq!(addr, addr2);
+        assert_eq!(addr.user(), "something");
+        assert_eq!(addr.domain(), "[2606:4700:4700::1111]");
+        assert_eq!(addr2.user(), "something");
+        assert_eq!(addr2.domain(), "[2606:4700:4700::1111]");
+    }
+
+    #[test]
+    fn check_parts() {
+        assert!(Address::check_user("aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa").is_err());
+        assert!(
+            Address::check_domain("aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa.com").is_err()
+        );
+    }
 }

src/base64.rs

@@ -0,0 +1,12 @@
+use ::base64::{
+    engine::{general_purpose::STANDARD, Engine},
+    DecodeError,
+};
+
+pub(crate) fn encode<T: AsRef<[u8]>>(input: T) -> String {
+    STANDARD.encode(input)
+}
+
+pub(crate) fn decode<T: AsRef<[u8]>>(input: T) -> Result<Vec<u8>, DecodeError> {
+    STANDARD.decode(input)
+}

src/error.rs

@@ -1,3 +1,5 @@
+//! Error type for email messages
+
 use std::{
     error::Error as StdError,
     fmt::{self, Display, Formatter},

src/executor.rs

@@ -0,0 +1,298 @@
+use std::fmt::Debug;
+#[cfg(feature = "smtp-transport")]
+use std::future::Future;
+#[cfg(feature = "file-transport")]
+use std::io::Result as IoResult;
+#[cfg(feature = "file-transport")]
+use std::path::Path;
+#[cfg(feature = "smtp-transport")]
+use std::time::Duration;
+
+use async_trait::async_trait;
+#[cfg(all(feature = "smtp-transport", feature = "async-std1"))]
+use futures_util::future::BoxFuture;
+
+#[cfg(all(
+    feature = "smtp-transport",
+    any(feature = "tokio1", feature = "async-std1")
+))]
+use crate::transport::smtp::client::AsyncSmtpConnection;
+#[cfg(all(
+    feature = "smtp-transport",
+    any(feature = "tokio1", feature = "async-std1")
+))]
+use crate::transport::smtp::client::Tls;
+#[cfg(all(
+    feature = "smtp-transport",
+    any(feature = "tokio1", feature = "async-std1")
+))]
+use crate::transport::smtp::extension::ClientId;
+#[cfg(all(
+    feature = "smtp-transport",
+    any(feature = "tokio1", feature = "async-std1")
+))]
+use crate::transport::smtp::Error;
+
+/// Async executor abstraction trait
+///
+/// Used by [`AsyncSmtpTransport`], [`AsyncSendmailTransport`] and [`AsyncFileTransport`]
+/// in order to be able to work with different async runtimes.
+///
+/// [`AsyncSmtpTransport`]: crate::AsyncSmtpTransport
+/// [`AsyncSendmailTransport`]: crate::AsyncSendmailTransport
+/// [`AsyncFileTransport`]: crate::AsyncFileTransport
+#[cfg_attr(docsrs, doc(cfg(any(feature = "tokio1", feature = "async-std1"))))]
+#[async_trait]
+pub trait Executor: Debug + Send + Sync + 'static + private::Sealed {
+    #[cfg(feature = "smtp-transport")]
+    #[allow(private_bounds)]
+    type Handle: SpawnHandle;
+    #[cfg(feature = "smtp-transport")]
+    type Sleep: Future<Output = ()> + Send + 'static;
+
+    #[doc(hidden)]
+    #[cfg(feature = "smtp-transport")]
+    fn spawn<F>(fut: F) -> Self::Handle
+    where
+        F: Future<Output = ()> + Send + 'static,
+        F::Output: Send + 'static;
+
+    #[doc(hidden)]
+    #[cfg(feature = "smtp-transport")]
+    fn sleep(duration: Duration) -> Self::Sleep;
+
+    #[doc(hidden)]
+    #[cfg(feature = "smtp-transport")]
+    async fn connect(
+        hostname: &str,
+        port: u16,
+        timeout: Option<Duration>,
+        hello_name: &ClientId,
+        tls: &Tls,
+    ) -> Result<AsyncSmtpConnection, Error>;
+
+    #[doc(hidden)]
+    #[cfg(feature = "file-transport-envelope")]
+    async fn fs_read(path: &Path) -> IoResult<Vec<u8>>;
+
+    #[doc(hidden)]
+    #[cfg(feature = "file-transport")]
+    async fn fs_write(path: &Path, contents: &[u8]) -> IoResult<()>;
+}
+
+#[doc(hidden)]
+#[cfg(feature = "smtp-transport")]
+#[async_trait]
+pub(crate) trait SpawnHandle: Debug + Send + Sync + 'static + private::Sealed {
+    async fn shutdown(&self);
+}
+
+/// Async [`Executor`] using `tokio` `1.x`
+///
+/// Used by [`AsyncSmtpTransport`], [`AsyncSendmailTransport`] and [`AsyncFileTransport`]
+/// in order to be able to work with different async runtimes.
+///
+/// [`AsyncSmtpTransport`]: crate::AsyncSmtpTransport
+/// [`AsyncSendmailTransport`]: crate::AsyncSendmailTransport
+/// [`AsyncFileTransport`]: crate::AsyncFileTransport
+#[allow(missing_copy_implementations)]
+#[non_exhaustive]
+#[cfg(feature = "tokio1")]
+#[cfg_attr(docsrs, doc(cfg(feature = "tokio1")))]
+#[derive(Debug)]
+pub struct Tokio1Executor;
+
+#[async_trait]
+#[cfg(feature = "tokio1")]
+impl Executor for Tokio1Executor {
+    #[cfg(feature = "smtp-transport")]
+    type Handle = tokio1_crate::task::JoinHandle<()>;
+    #[cfg(feature = "smtp-transport")]
+    type Sleep = tokio1_crate::time::Sleep;
+
+    #[cfg(feature = "smtp-transport")]
+    fn spawn<F>(fut: F) -> Self::Handle
+    where
+        F: Future<Output = ()> + Send + 'static,
+        F::Output: Send + 'static,
+    {
+        tokio1_crate::spawn(fut)
+    }
+
+    #[cfg(feature = "smtp-transport")]
+    fn sleep(duration: Duration) -> Self::Sleep {
+        tokio1_crate::time::sleep(duration)
+    }
+
+    #[cfg(feature = "smtp-transport")]
+    async fn connect(
+        hostname: &str,
+        port: u16,
+        timeout: Option<Duration>,
+        hello_name: &ClientId,
+        tls: &Tls,
+    ) -> Result<AsyncSmtpConnection, Error> {
+        #[allow(clippy::match_single_binding)]
+        let tls_parameters = match tls {
+            #[cfg(any(feature = "tokio1-native-tls", feature = "tokio1-rustls"))]
+            Tls::Wrapper(tls_parameters) => Some(tls_parameters.clone()),
+            _ => None,
+        };
+        #[allow(unused_mut)]
+        let mut conn = AsyncSmtpConnection::connect_tokio1(
+            (hostname, port),
+            timeout,
+            hello_name,
+            tls_parameters,
+            None,
+        )
+        .await?;
+
+        #[cfg(any(feature = "tokio1-native-tls", feature = "tokio1-rustls"))]
+        match tls {
+            Tls::Opportunistic(tls_parameters) => {
+                if conn.can_starttls() {
+                    conn.starttls(tls_parameters.clone(), hello_name).await?;
+                }
+            }
+            Tls::Required(tls_parameters) => {
+                conn.starttls(tls_parameters.clone(), hello_name).await?;
+            }
+            _ => (),
+        }
+
+        Ok(conn)
+    }
+
+    #[cfg(feature = "file-transport-envelope")]
+    async fn fs_read(path: &Path) -> IoResult<Vec<u8>> {
+        tokio1_crate::fs::read(path).await
+    }
+
+    #[cfg(feature = "file-transport")]
+    async fn fs_write(path: &Path, contents: &[u8]) -> IoResult<()> {
+        tokio1_crate::fs::write(path, contents).await
+    }
+}
+
+#[cfg(all(feature = "smtp-transport", feature = "tokio1"))]
+#[async_trait]
+impl SpawnHandle for tokio1_crate::task::JoinHandle<()> {
+    async fn shutdown(&self) {
+        self.abort();
+    }
+}
+
+/// Async [`Executor`] using `async-std` `1.x`
+///
+/// Used by [`AsyncSmtpTransport`], [`AsyncSendmailTransport`] and [`AsyncFileTransport`]
+/// in order to be able to work with different async runtimes.
+///
+/// [`AsyncSmtpTransport`]: crate::AsyncSmtpTransport
+/// [`AsyncSendmailTransport`]: crate::AsyncSendmailTransport
+/// [`AsyncFileTransport`]: crate::AsyncFileTransport
+#[allow(missing_copy_implementations)]
+#[non_exhaustive]
+#[cfg(feature = "async-std1")]
+#[cfg_attr(docsrs, doc(cfg(feature = "async-std1")))]
+#[derive(Debug)]
+pub struct AsyncStd1Executor;
+
+#[async_trait]
+#[cfg(feature = "async-std1")]
+impl Executor for AsyncStd1Executor {
+    #[cfg(feature = "smtp-transport")]
+    type Handle = futures_util::future::AbortHandle;
+    #[cfg(feature = "smtp-transport")]
+    type Sleep = BoxFuture<'static, ()>;
+
+    #[cfg(feature = "smtp-transport")]
+    fn spawn<F>(fut: F) -> Self::Handle
+    where
+        F: Future<Output = ()> + Send + 'static,
+        F::Output: Send + 'static,
+    {
+        let (handle, registration) = futures_util::future::AbortHandle::new_pair();
+        async_std::task::spawn(futures_util::future::Abortable::new(fut, registration));
+        handle
+    }
+
+    #[cfg(feature = "smtp-transport")]
+    fn sleep(duration: Duration) -> Self::Sleep {
+        let fut = async_std::task::sleep(duration);
+        Box::pin(fut)
+    }
+
+    #[cfg(feature = "smtp-transport")]
+    async fn connect(
+        hostname: &str,
+        port: u16,
+        timeout: Option<Duration>,
+        hello_name: &ClientId,
+        tls: &Tls,
+    ) -> Result<AsyncSmtpConnection, Error> {
+        #[allow(clippy::match_single_binding)]
+        let tls_parameters = match tls {
+            #[cfg(feature = "async-std1-rustls")]
+            Tls::Wrapper(tls_parameters) => Some(tls_parameters.clone()),
+            _ => None,
+        };
+        #[allow(unused_mut)]
+        let mut conn = AsyncSmtpConnection::connect_asyncstd1(
+            (hostname, port),
+            timeout,
+            hello_name,
+            tls_parameters,
+        )
+        .await?;
+
+        #[cfg(feature = "async-std1-rustls")]
+        match tls {
+            Tls::Opportunistic(tls_parameters) => {
+                if conn.can_starttls() {
+                    conn.starttls(tls_parameters.clone(), hello_name).await?;
+                }
+            }
+            Tls::Required(tls_parameters) => {
+                conn.starttls(tls_parameters.clone(), hello_name).await?;
+            }
+            _ => (),
+        }
+
+        Ok(conn)
+    }
+
+    #[cfg(feature = "file-transport-envelope")]
+    async fn fs_read(path: &Path) -> IoResult<Vec<u8>> {
+        async_std::fs::read(path).await
+    }
+
+    #[cfg(feature = "file-transport")]
+    async fn fs_write(path: &Path, contents: &[u8]) -> IoResult<()> {
+        async_std::fs::write(path, contents).await
+    }
+}
+
+#[cfg(all(feature = "smtp-transport", feature = "async-std1"))]
+#[async_trait]
+impl SpawnHandle for futures_util::future::AbortHandle {
+    async fn shutdown(&self) {
+        self.abort();
+    }
+}
+
+mod private {
+    pub trait Sealed {}
+
+    #[cfg(feature = "tokio1")]
+    impl Sealed for super::Tokio1Executor {}
+
+    #[cfg(feature = "async-std1")]
+    impl Sealed for super::AsyncStd1Executor {}
+
+    #[cfg(all(feature = "smtp-transport", feature = "tokio1"))]
+    impl Sealed for tokio1_crate::task::JoinHandle<()> {}
+
+    #[cfg(all(feature = "smtp-transport", feature = "async-std1"))]
+    impl Sealed for futures_util::future::AbortHandle {}
+}

src/lib.rs

@@ -4,176 +4,326 @@
 //! * Pluggable email transports
 //! * Unicode support
 //! * Secure defaults
+//! * Async support
 //!
-//! Lettre requires Rust 1.45 or newer.
+//! Lettre requires Rust 1.74 or newer.
 //!
-//! ## Optional features
+//! ## Features
+//!
+//! This section lists each lettre feature and briefly explains it.
+//! More info about each module can be found in the corresponding module page.
+//!
+//! Features with `📫` near them are enabled by default.
+//!
+//! ### Typed message builder
+//!
+//! _Strongly typed [`message`] builder_
+//!
+//! * **builder** 📫: Enable the [`Message`] builder
+//! * **hostname** 📫: Try to use the actual system hostname in the `Message-ID` header
+//!
+//! ### SMTP transport
+//!
+//! _Send emails using [`SMTP`]_
+//!
+//! * **smtp-transport** 📫: Enable the SMTP transport
+//! * **pool** 📫: Connection pool for SMTP transport
+//! * **hostname** 📫: Try to use the actual system hostname for the SMTP `CLIENTID`
+//!
+//! #### SMTP over TLS via the native-tls crate
+//!
+//! _Secure SMTP connections using TLS from the `native-tls` crate_
+//!
+//! Uses schannel on Windows, Security-Framework on macOS, and OpenSSL
+//! on all other platforms.
+//!
+//! * **native-tls** 📫: TLS support for the synchronous version of the API
+//! * **tokio1-native-tls**: TLS support for the `tokio1` async version of the API
+//!
+//! NOTE: native-tls isn't supported with `async-std`
+//!
+//! ##### Building lettre with OpenSSL
+//!
+//! When building lettre with native-tls on a system that makes
+//! use of OpenSSL, the following packages will need to be installed
+//! in order for the build and the compiled program to run properly.
+//!
+//! | Distro       | Build-time packages        | Runtime packages             |
+//! | ------------ | -------------------------- | ---------------------------- |
+//! | Debian       | `pkg-config`, `libssl-dev` | `libssl3`, `ca-certificates` |
+//! | Alpine Linux | `pkgconf`, `openssl-dev`   | `libssl3`, `ca-certificates` |
+//!
+//! #### SMTP over TLS via the boring crate (Boring TLS)
+//!
+//! _Secure SMTP connections using TLS from the `boring-tls` crate_
+//!
+//! * **boring-tls**: TLS support for the synchronous version of the API
+//! * **tokio1-boring-tls**: TLS support for the `tokio1` async version of the API
+//!
+//! NOTE: boring-tls isn't supported with `async-std`
+//!
+//! #### SMTP over TLS via the rustls crate
+//!
+//! _Secure SMTP connections using TLS from the `rustls` crate_
+//!
+//! * **rustls**: TLS support for the synchronous version of the API
+//! * **tokio1-rustls**: TLS support for the `tokio1` async version of the API
+//! * **async-std1-rustls**: TLS support for the `async-std1` async version of the API
+//!
+//! ##### rustls crypto backends
+//!
+//! _The crypto implementation to use with rustls_
+//!
+//! When the `rustls` feature is enabled, one of the following crypto backends MUST also
+//! be enabled.
+//!
+//! * **aws-lc-rs**: use [AWS-LC] (via [`aws-lc-rs`]) as the `rustls` crypto backend
+//! * **ring**: use [`ring`] as the `rustls` crypto backend
+//!
+//! When enabling `aws-lc-rs`, the `fips` feature can also be enabled to have
+//! rustls use the FIPS certified module of AWS-LC.
+//!
+//! `aws-lc-rs` may require cmake on some platforms to compile.
+//! `fips` always requires cmake and the Go compiler to compile.
+//!
+//! ##### rustls certificate verification backend
+//!
+//! _The TLS certificate verification backend to use with rustls_
+//!
+//! When the `rustls` feature is enabled, one of the following verification backends
+//! MUST also be enabled.
+//!
+//! * **rustls-native-certs**: verify TLS certificates using the platform's native certificate store (see [`rustls-native-certs`])
+//! * **webpki-roots**: verify TLS certificates against Mozilla's root certificates (see [`webpki-roots`])
+//!
+//! For the `rustls-native-certs` backend to work correctly, the following packages
+//! will need to be installed in order for the build stage and the compiled program
+//! to run properly.
+//!
+//! | Distro       | Build-time packages        | Runtime packages             |
+//! | ------------ | -------------------------- | ---------------------------- |
+//! | Debian       | none                       | `ca-certificates`            |
+//! | Alpine Linux | none                       | `ca-certificates`            |
+//!
+//! ### Sendmail transport
+//!
+//! _Send emails using the [`sendmail`] command_
+//!
+//! * **sendmail-transport**: Enable the `sendmail` transport
+//!
+//! ### File transport
+//!
+//! _Save emails as an `.eml` [`file`]_
+//!
+//! * **file-transport**: Enable the file transport (saves emails into an `.eml` file)
+//! * **file-transport-envelope**: Allow writing the envelope into a JSON file (additionally saves envelopes into a `.json` file)
+//!
+//! ### Async execution runtimes
+//!
+//! _Use [tokio] or [async-std] as an async execution runtime for sending emails_
+//!
+//! The correct runtime version must be chosen in order for lettre to work correctly.
+//! For example, when sending emails from a Tokio 1.x context, the Tokio 1.x executor
+//! ([`Tokio1Executor`]) must be used. Using a different version (for example Tokio 0.2.x),
+//! or async-std, would result in a runtime panic.
+//!
+//! * **tokio1**: Allow to asynchronously send emails using [Tokio 1.x]
+//! * **async-std1**: Allow to asynchronously send emails using [async-std 1.x]
+//!
+//! NOTE: native-tls isn't supported with `async-std`
+//!
+//! ### Misc features
+//!
+//! _Additional features_
 //!
-//! * **builder**: Message builder
-//! * **file-transport**: Transport that write messages into a file
-//! * **file-transport-envelope**: Allow writing the envelope into a JSON file
-//! * **smtp-transport**: Transport over SMTP
-//! * **sendmail-transport**: Transport over SMTP
-//! * **rustls-tls**: TLS support with the `rustls` crate
-//! * **native-tls**: TLS support with the `native-tls` crate
-//! * **tokio02**: Allow to asyncronously send emails using tokio 0.2.x
-//! * **tokio02-rustls-tls**: Async TLS support with the `rustls` crate using tokio 0.2
-//! * **tokio02-native-tls**: Async TLS support with the `native-tls` crate using tokio 0.2
-//! * **tokio1**: Allow to asyncronously send emails using tokio 1.x
-//! * **tokio1-rustls-tls**: Async TLS support with the `rustls` crate using tokio 1.x
-//! * **tokio1-native-tls**: Async TLS support with the `native-tls` crate using tokio 1.x
-//! * **async-std1**: Allow to asynchronously send emails using async-std 1.x
-//! * NOTE: native-tls isn't supported with async-std at the moment
-//! * **async-std1-rustls-tls**: Async TLS support with the `rustls` crate using async-std 1.x
-//! * **r2d2**: Connection pool for SMTP transport
-//! * **tracing**: Logging using the `tracing` crate
 //! * **serde**: Serialization/Deserialization of entities
-//! * **hostname**: Ability to try to use actual hostname in SMTP transaction
+//! * **tracing**: Logging using the `tracing` crate
+//! * **mime03**: Allow creating a [`ContentType`] from an existing [mime 0.3] `Mime` struct
+//! * **dkim**: Add support for signing email with DKIM
+//! * **web**: WebAssembly support using the `web-time` crate for time operations
+//!
+//! [`SMTP`]: crate::transport::smtp
+//! [`sendmail`]: crate::transport::sendmail
+//! [`file`]: crate::transport::file
+//! [`ContentType`]: crate::message::header::ContentType
+//! [tokio]: https://docs.rs/tokio/1
+//! [async-std]: https://docs.rs/async-std/1
+//! [AWS-LC]: https://github.com/aws/aws-lc
+//! [`aws-lc-rs`]: https://crates.io/crates/aws-lc-rs
+//! [`ring`]: https://crates.io/crates/ring
+//! [`rustls-native-certs`]: https://crates.io/crates/rustls-native-certs
+//! [`webpki-roots`]: https://crates.io/crates/webpki-roots
+//! [Tokio 1.x]: https://docs.rs/tokio/1
+//! [async-std 1.x]: https://docs.rs/async-std/1
+//! [mime 0.3]: https://docs.rs/mime/0.3
+//! [DKIM]: https://datatracker.ietf.org/doc/html/rfc6376
 
-#![doc(html_root_url = "https://docs.rs/crate/lettre/0.10.0-alpha.5")]
+#![doc(html_root_url = "https://docs.rs/crate/lettre/0.11.15")]
 #![doc(html_favicon_url = "https://lettre.rs/favicon.ico")]
 #![doc(html_logo_url = "https://avatars0.githubusercontent.com/u/15113230?v=4")]
 #![forbid(unsafe_code)]
 #![deny(
+    unreachable_pub,
     missing_copy_implementations,
     trivial_casts,
     trivial_numeric_casts,
     unstable_features,
     unused_import_braces,
-    rust_2018_idioms
+    rust_2018_idioms,
+    clippy::string_add,
+    clippy::string_add_assign,
+    clippy::clone_on_ref_ptr,
+    clippy::verbose_file_reads,
+    clippy::unnecessary_self_imports,
+    clippy::string_to_string,
+    clippy::mem_forget,
+    clippy::cast_lossless,
+    clippy::inefficient_to_string,
+    clippy::inline_always,
+    clippy::linkedlist,
+    clippy::macro_use_imports,
+    clippy::manual_assert,
+    clippy::unnecessary_join,
+    clippy::wildcard_imports,
+    clippy::str_to_string,
+    clippy::empty_structs_with_brackets,
+    clippy::zero_sized_map_values,
+    clippy::manual_let_else,
+    clippy::semicolon_if_nothing_returned,
+    clippy::unnecessary_wraps,
+    clippy::doc_markdown,
+    clippy::explicit_iter_loop,
+    clippy::redundant_closure_for_method_calls,
+    // Rust 1.86: clippy::unnecessary_semicolon,
 )]
 #![cfg_attr(docsrs, feature(doc_cfg))]
 
+#[cfg(not(lettre_ignore_tls_mismatch))]
+mod compiletime_checks {
+    #[cfg(all(feature = "rustls", not(feature = "aws-lc-rs"), not(feature = "ring")))]
+    compile_error!(
+        "feature `rustls` also requires either the `aws-lc-rs` or the `ring` feature to
+    be enabled"
+    );
+
+    #[cfg(all(
+        feature = "rustls",
+        not(feature = "rustls-native-certs"),
+        not(feature = "webpki-roots")
+    ))]
+    compile_error!(
+        "feature `rustls` also requires either the `rustls-native-certs` or the `webpki-roots` feature to
+    be enabled"
+    );
+
+    #[cfg(all(feature = "native-tls", feature = "boring-tls"))]
+    compile_error!("feature \"native-tls\" and feature \"boring-tls\" cannot be enabled at the same time, otherwise
+    the executable will fail to link.");
+
+    #[cfg(all(
+        feature = "tokio1",
+        feature = "native-tls",
+        not(feature = "tokio1-native-tls")
+    ))]
+    compile_error!("Lettre is being built with the `tokio1` and the `native-tls` features, but the `tokio1-native-tls` feature hasn't been turned on.
+    If you were trying to opt into `rustls` and did not activate `native-tls`, disable the default-features of lettre in `Cargo.toml` and manually add the required features.
+    Make sure to apply the same to any of your crate dependencies that use the `lettre` crate.");
+
+    #[cfg(all(feature = "tokio1", feature = "rustls", not(feature = "tokio1-rustls")))]
+    compile_error!("Lettre is being built with the `tokio1` and the `rustls` features, but the `tokio1-rustls` feature hasn't been turned on.
+    If you'd like to use `native-tls` make sure that the `rustls` feature hasn't been enabled by mistake.
+    Make sure to apply the same to any of your crate dependencies that use the `lettre` crate.");
+
+    #[cfg(all(
+        feature = "tokio1",
+        feature = "boring-tls",
+        not(feature = "tokio1-boring-tls")
+    ))]
+    compile_error!("Lettre is being built with the `tokio1` and the `boring-tls` features, but the `tokio1-boring-tls` feature hasn't been turned on.
+    If you'd like to use `boring-tls` make sure that the `rustls` feature hasn't been enabled by mistake.
+    Make sure to apply the same to any of your crate dependencies that use the `lettre` crate.");
+
+    #[cfg(all(feature = "async-std1", feature = "native-tls"))]
+    compile_error!("Lettre is being built with the `async-std1` and the `native-tls` features, but the async-std integration doesn't support native-tls yet.
+If you'd like to work on the issue please take a look at https://github.com/lettre/lettre/issues/576.
+If you were trying to opt into `rustls` and did not activate `native-tls`, disable the default-features of lettre in `Cargo.toml` and manually add the required features.
+Make sure to apply the same to any of your crate dependencies that use the `lettre` crate.");
+
+    #[cfg(all(
+        feature = "async-std1",
+        feature = "rustls",
+        not(feature = "async-std1-rustls")
+    ))]
+    compile_error!("Lettre is being built with the `async-std1` and the `rustls` features, but the `async-std1-rustls` feature hasn't been turned on.
+If you'd like to use `native-tls` make sure that the `rustls` hasn't been enabled by mistake.
+Make sure to apply the same to any of your crate dependencies that use the `lettre` crate.");
+}
+
 pub mod address;
+#[cfg(any(feature = "smtp-transport", feature = "dkim"))]
+mod base64;
 pub mod error;
+#[cfg(any(feature = "tokio1", feature = "async-std1"))]
+mod executor;
 #[cfg(feature = "builder")]
 #[cfg_attr(docsrs, doc(cfg(feature = "builder")))]
 pub mod message;
+#[cfg(feature = "rustls")]
+mod rustls_crypto;
+mod time;
 pub mod transport;
 
-#[cfg(feature = "builder")]
-#[macro_use]
-extern crate hyperx;
+use std::error::Error as StdError;
 
+#[cfg(feature = "async-std1")]
+pub use self::executor::AsyncStd1Executor;
+#[cfg(any(feature = "tokio1", feature = "async-std1"))]
+pub use self::executor::Executor;
+#[cfg(feature = "tokio1")]
+pub use self::executor::Tokio1Executor;
+#[cfg(any(feature = "tokio1", feature = "async-std1"))]
+#[doc(inline)]
+pub use self::transport::AsyncTransport;
 pub use crate::address::Address;
-use crate::address::Envelope;
-use crate::error::Error;
 #[cfg(feature = "builder")]
+#[doc(inline)]
 pub use crate::message::Message;
+#[cfg(all(
+    feature = "file-transport",
+    any(feature = "tokio1", feature = "async-std1")
+))]
+#[doc(inline)]
+pub use crate::transport::file::AsyncFileTransport;
 #[cfg(feature = "file-transport")]
+#[doc(inline)]
 pub use crate::transport::file::FileTransport;
+#[cfg(all(
+    feature = "sendmail-transport",
+    any(feature = "tokio1", feature = "async-std1")
+))]
+#[doc(inline)]
+pub use crate::transport::sendmail::AsyncSendmailTransport;
 #[cfg(feature = "sendmail-transport")]
+#[doc(inline)]
 pub use crate::transport::sendmail::SendmailTransport;
 #[cfg(all(
     feature = "smtp-transport",
-    any(feature = "tokio02", feature = "tokio1")
+    any(feature = "tokio1", feature = "async-std1")
 ))]
 pub use crate::transport::smtp::AsyncSmtpTransport;
-#[cfg(all(feature = "smtp-transport", feature = "async-std1"))]
-pub use crate::transport::smtp::AsyncStd1Connector;
 #[cfg(feature = "smtp-transport")]
 pub use crate::transport::smtp::SmtpTransport;
-#[cfg(all(feature = "smtp-transport", feature = "tokio02"))]
-pub use crate::transport::smtp::Tokio02Connector;
-#[cfg(all(feature = "smtp-transport", feature = "tokio1"))]
-pub use crate::transport::smtp::Tokio1Connector;
-#[cfg(any(feature = "async-std1", feature = "tokio02", feature = "tokio1"))]
-use async_trait::async_trait;
+#[doc(inline)]
+pub use crate::transport::Transport;
+use crate::{address::Envelope, error::Error};
 
-/// Blocking Transport method for emails
-pub trait Transport {
-    /// Response produced by the Transport
-    type Ok;
-    /// Error produced by the Transport
-    type Error;
-
-    /// Sends the email
-    #[cfg(feature = "builder")]
-    #[cfg_attr(docsrs, doc(cfg(feature = "builder")))]
-    fn send(&self, message: &Message) -> Result<Self::Ok, Self::Error> {
-        let raw = message.formatted();
-        self.send_raw(message.envelope(), &raw)
-    }
-
-    fn send_raw(&self, envelope: &Envelope, email: &[u8]) -> Result<Self::Ok, Self::Error>;
-}
-
-/// async-std 1.x based Transport method for emails
-#[cfg(feature = "async-std1")]
-#[cfg_attr(docsrs, doc(cfg(feature = "async-std1")))]
-#[async_trait]
-pub trait AsyncStd1Transport {
-    /// Response produced by the Transport
-    type Ok;
-    /// Error produced by the Transport
-    type Error;
-
-    /// Sends the email
-    #[cfg(feature = "builder")]
-    #[cfg_attr(docsrs, doc(cfg(feature = "builder")))]
-    // TODO take &Message
-    async fn send(&self, message: Message) -> Result<Self::Ok, Self::Error> {
-        let raw = message.formatted();
-        let envelope = message.envelope();
-        self.send_raw(&envelope, &raw).await
-    }
-
-    async fn send_raw(&self, envelope: &Envelope, email: &[u8]) -> Result<Self::Ok, Self::Error>;
-}
-
-/// tokio 0.2.x based Transport method for emails
-#[cfg(feature = "tokio02")]
-#[cfg_attr(docsrs, doc(cfg(feature = "tokio02")))]
-#[async_trait]
-pub trait Tokio02Transport {
-    /// Response produced by the Transport
-    type Ok;
-    /// Error produced by the Transport
-    type Error;
-
-    /// Sends the email
-    #[cfg(feature = "builder")]
-    #[cfg_attr(docsrs, doc(cfg(feature = "builder")))]
-    // TODO take &Message
-    async fn send(&self, message: Message) -> Result<Self::Ok, Self::Error> {
-        let raw = message.formatted();
-        let envelope = message.envelope();
-        self.send_raw(&envelope, &raw).await
-    }
-
-    async fn send_raw(&self, envelope: &Envelope, email: &[u8]) -> Result<Self::Ok, Self::Error>;
-}
-
-/// tokio 1.x based Transport method for emails
-#[cfg(feature = "tokio1")]
-#[cfg_attr(docsrs, doc(cfg(feature = "tokio1")))]
-#[async_trait]
-pub trait Tokio1Transport {
-    /// Response produced by the Transport
-    type Ok;
-    /// Error produced by the Transport
-    type Error;
-
-    /// Sends the email
-    #[cfg(feature = "builder")]
-    #[cfg_attr(docsrs, doc(cfg(feature = "builder")))]
-    // TODO take &Message
-    async fn send(&self, message: Message) -> Result<Self::Ok, Self::Error> {
-        let raw = message.formatted();
-        let envelope = message.envelope();
-        self.send_raw(&envelope, &raw).await
-    }
-
-    async fn send_raw(&self, envelope: &Envelope, email: &[u8]) -> Result<Self::Ok, Self::Error>;
-}
+pub(crate) type BoxError = Box<dyn StdError + Send + Sync>;
 
 #[cfg(test)]
 #[cfg(feature = "builder")]
 mod test {
     use super::*;
-    use crate::message::{header, Mailbox, Mailboxes};
-    use hyperx::header::Headers;
-    use std::convert::TryFrom;
+    use crate::message::{header, header::Headers, Mailbox, Mailboxes};
 
     #[test]
     fn envelope_from_headers() {
@@ -201,9 +351,9 @@ mod test {
         let to = Mailboxes::new().with("amousset@example.com".parse().unwrap());
 
         let mut headers = Headers::new();
-        headers.set(header::From(from));
-        headers.set(header::Sender(sender));
-        headers.set(header::To(to));
+        headers.set(header::From::from(from));
+        headers.set(header::Sender::from(sender));
+        headers.set(header::To::from(to));
 
         assert_eq!(
             Envelope::try_from(&headers).unwrap(),
@@ -221,8 +371,8 @@ mod test {
         let sender = Mailbox::new(None, "kayo2@example.com".parse().unwrap());
 
         let mut headers = Headers::new();
-        headers.set(header::From(from));
-        headers.set(header::Sender(sender));
+        headers.set(header::From::from(from));
+        headers.set(header::Sender::from(sender));
 
         assert!(Envelope::try_from(&headers).is_err(),);
     }

src/message/attachment.rs

@@ -0,0 +1,145 @@
+use crate::message::{
+    header::{self, ContentType},
+    IntoBody, SinglePart,
+};
+
+/// `SinglePart` builder for attachments
+///
+/// Allows building attachment parts easily.
+#[derive(Clone)]
+pub struct Attachment {
+    disposition: Disposition,
+}
+
+#[derive(Clone)]
+enum Disposition {
+    /// File name
+    Attached(String),
+    /// Content id
+    Inline(String),
+}
+
+impl Attachment {
+    /// Create a new attachment
+    ///
+    /// This attachment will be displayed as a normal attachment,
+    /// with the chosen `filename` appearing as the file name.
+    ///
+    /// ```rust
+    /// # use std::error::Error;
+    /// use std::fs;
+    ///
+    /// use lettre::message::{header::ContentType, Attachment};
+    ///
+    /// # fn main() -> Result<(), Box<dyn Error>> {
+    /// let filename = String::from("invoice.pdf");
+    /// # if false {
+    /// let filebody = fs::read("invoice.pdf")?;
+    /// # }
+    /// # let filebody = fs::read("docs/lettre.png")?;
+    /// let content_type = ContentType::parse("application/pdf").unwrap();
+    /// let attachment = Attachment::new(filename).body(filebody, content_type);
+    ///
+    /// // The document `attachment` will show up as a normal attachment.
+    /// # Ok(())
+    /// # }
+    /// ```
+    pub fn new(filename: String) -> Self {
+        Attachment {
+            disposition: Disposition::Attached(filename),
+        }
+    }
+
+    /// Create a new inline attachment
+    ///
+    /// This attachment should be displayed inline into the message
+    /// body:
+    ///
+    /// ```html
+    /// <img src="cid:123">
+    /// ```
+    ///
+    ///
+    /// ```rust
+    /// # use std::error::Error;
+    /// use std::fs;
+    ///
+    /// use lettre::message::{header::ContentType, Attachment};
+    ///
+    /// # fn main() -> Result<(), Box<dyn Error>> {
+    /// let content_id = String::from("123");
+    /// # if false {
+    /// let filebody = fs::read("image.jpg")?;
+    /// # }
+    /// # let filebody = fs::read("docs/lettre.png")?;
+    /// let content_type = ContentType::parse("image/jpeg").unwrap();
+    /// let attachment = Attachment::new_inline(content_id).body(filebody, content_type);
+    ///
+    /// // The image `attachment` will display inline into the email.
+    /// # Ok(())
+    /// # }
+    /// ```
+    pub fn new_inline(content_id: String) -> Self {
+        Attachment {
+            disposition: Disposition::Inline(content_id),
+        }
+    }
+
+    /// Build the attachment into a [`SinglePart`] which can then be used to build the rest of the email
+    ///
+    /// Look at the [Complex MIME body example](crate::message#complex-mime-body)
+    /// to see how [`SinglePart`] can be put into the email.
+    pub fn body<T: IntoBody>(self, content: T, content_type: ContentType) -> SinglePart {
+        let mut builder = SinglePart::builder();
+        builder = match self.disposition {
+            Disposition::Attached(filename) => {
+                builder.header(header::ContentDisposition::attachment(&filename))
+            }
+            Disposition::Inline(content_id) => builder
+                .header(header::ContentId::from(format!("<{content_id}>")))
+                .header(header::ContentDisposition::inline()),
+        };
+        builder = builder.header(content_type);
+        builder.body(content)
+    }
+}
+
+#[cfg(test)]
+mod tests {
+    use crate::message::header::ContentType;
+
+    #[test]
+    fn attachment() {
+        let part = super::Attachment::new(String::from("test.txt")).body(
+            String::from("Hello world!"),
+            ContentType::parse("text/plain").unwrap(),
+        );
+        assert_eq!(
+            &String::from_utf8_lossy(&part.formatted()),
+            concat!(
+                "Content-Disposition: attachment; filename=\"test.txt\"\r\n",
+                "Content-Type: text/plain\r\n",
+                "Content-Transfer-Encoding: 7bit\r\n\r\n",
+                "Hello world!\r\n",
+            )
+        );
+    }
+
+    #[test]
+    fn attachment_inline() {
+        let part = super::Attachment::new_inline(String::from("id")).body(
+            String::from("Hello world!"),
+            ContentType::parse("text/plain").unwrap(),
+        );
+        assert_eq!(
+            &String::from_utf8_lossy(&part.formatted()),
+            concat!(
+                "Content-ID: <id>\r\n",
+                "Content-Disposition: inline\r\n",
+                "Content-Type: text/plain\r\n",
+                "Content-Transfer-Encoding: 7bit\r\n\r\n",
+                "Hello world!\r\n"
+            )
+        );
+    }
+}

src/message/body.rs

@@ -1,5 +1,4 @@
-use std::io::{self, Write};
-use std::ops::Deref;
+use std::{mem, ops::Deref};
 
 use crate::message::header::ContentTransferEncoding;
 
@@ -16,7 +15,9 @@ pub struct Body {
 /// makes for a more efficient `Content-Transfer-Encoding` to be chosen.
 #[derive(Debug, Clone)]
 pub enum MaybeString {
+    /// Binary data
     Binary(Vec<u8>),
+    /// UTF-8 string
     String(String),
 }
 
@@ -28,13 +29,16 @@ impl Body {
     /// Automatically chooses the most efficient encoding between
     /// `7bit`, `quoted-printable` and `base64`.
     ///
+    /// If `String` is passed, line endings are converted to `CRLF`.
+    ///
     /// If `buf` is valid utf-8 a `String` should be supplied, as `String`s
     /// can be encoded as `7bit` or `quoted-printable`, while `Vec<u8>` always
     /// get encoded as `base64`.
     pub fn new<B: Into<MaybeString>>(buf: B) -> Self {
-        let buf: MaybeString = buf.into();
+        let mut buf: MaybeString = buf.into();
 
-        let encoding = buf.encoding();
+        let encoding = buf.encoding(false);
+        buf.encode_crlf();
         Self::new_impl(buf.into(), encoding)
     }
 
@@ -42,6 +46,8 @@ impl Body {
     ///
     /// [`Body::new`] is generally the better option.
     ///
+    /// If `String` is passed, line endings are converted to `CRLF`.
+    ///
     /// Returns an [`Err`] giving back the supplied `buf`, in case the chosen
     /// encoding would have resulted into `buf` being encoded
     /// into an invalid body.
@@ -49,12 +55,28 @@ impl Body {
         buf: B,
         encoding: ContentTransferEncoding,
     ) -> Result<Self, Vec<u8>> {
-        let buf: MaybeString = buf.into();
+        let mut buf: MaybeString = buf.into();
 
-        if !buf.is_encoding_ok(encoding) {
+        let best_encoding = buf.encoding(true);
+        let ok = match (encoding, best_encoding) {
+            (ContentTransferEncoding::SevenBit, ContentTransferEncoding::SevenBit) => true,
+            (
+                ContentTransferEncoding::EightBit,
+                ContentTransferEncoding::SevenBit | ContentTransferEncoding::EightBit,
+            ) => true,
+            (ContentTransferEncoding::SevenBit | ContentTransferEncoding::EightBit, _) => false,
+            (
+                ContentTransferEncoding::QuotedPrintable
+                | ContentTransferEncoding::Base64
+                | ContentTransferEncoding::Binary,
+                _,
+            ) => true,
+        };
+        if !ok {
             return Err(buf.into());
         }
 
+        buf.encode_crlf();
         Ok(Self::new_impl(buf.into(), encoding))
     }
 
@@ -80,36 +102,13 @@ impl Body {
                 Self::dangerous_pre_encoded(encoded, ContentTransferEncoding::QuotedPrintable)
             }
             ContentTransferEncoding::Base64 => {
-                let base64_len = buf.len() * 4 / 3 + 4;
-                let base64_endings_len = base64_len + base64_len / LINE_MAX_LENGTH;
+                let len = email_encoding::body::base64::encoded_len(buf.len());
 
-                let mut out = Vec::with_capacity(base64_endings_len);
-                {
-                    let writer = LineWrappingWriter::new(&mut out, LINE_MAX_LENGTH);
-                    let mut writer = base64::write::EncoderWriter::new(writer, base64::STANDARD);
+                let mut out = String::with_capacity(len);
+                email_encoding::body::base64::encode(&buf, &mut out)
+                    .expect("encode body as base64");
 
-                    // TODO: use writer.write_all(self.as_ref()).expect("base64 encoding never fails");
-
-                    // modified Write::write_all to work around base64 crate bug
-                    // TODO: remove once https://github.com/marshallpierce/rust-base64/issues/148 is fixed
-                    {
-                        let mut buf: &[u8] = buf.as_ref();
-                        while !buf.is_empty() {
-                            match writer.write(buf) {
-                                Ok(0) => {
-                                    // ignore 0 writes
-                                }
-                                Ok(n) => {
-                                    buf = &buf[n..];
-                                }
-                                Err(ref e) if e.kind() == std::io::ErrorKind::Interrupted => {}
-                                Err(e) => panic!("base64 encoding never fails: {}", e),
-                            }
-                        }
-                    }
-                }
-
-                Self::dangerous_pre_encoded(out, ContentTransferEncoding::Base64)
+                Self::dangerous_pre_encoded(out.into_bytes(), ContentTransferEncoding::Base64)
             }
         }
     }
@@ -142,33 +141,28 @@ impl Body {
 impl MaybeString {
     /// Suggests the best `Content-Transfer-Encoding` to be used for this `MaybeString`
     ///
-    /// If the `MaybeString` was created from a `String` composed only of US-ASCII
-    /// characters, with no lines longer than 1000 characters, then 7bit
-    /// encoding will be used, else quoted-printable will be chosen.
-    ///
-    /// If the `MaybeString` was instead created from a `Vec<u8>`, base64 encoding is always
-    /// chosen.
-    ///
-    /// `8bit` and `binary` encodings are never returned, as they may not be
-    /// supported by all SMTP servers.
-    pub fn encoding(&self) -> ContentTransferEncoding {
-        match &self {
-            Self::String(s) if is_7bit_encoded(s.as_ref()) => ContentTransferEncoding::SevenBit,
-            // TODO: consider when base64 would be a better option because of output size
-            Self::String(_) => ContentTransferEncoding::QuotedPrintable,
-            Self::Binary(_) => ContentTransferEncoding::Base64,
+    /// The `binary` encoding is never returned
+    fn encoding(&self, supports_utf8: bool) -> ContentTransferEncoding {
+        use email_encoding::body::Encoding;
+
+        let output = match self {
+            Self::String(s) => Encoding::choose(s.as_str(), supports_utf8),
+            Self::Binary(b) => Encoding::choose(b.as_slice(), supports_utf8),
+        };
+
+        match output {
+            Encoding::SevenBit => ContentTransferEncoding::SevenBit,
+            Encoding::EightBit => ContentTransferEncoding::EightBit,
+            Encoding::QuotedPrintable => ContentTransferEncoding::QuotedPrintable,
+            Encoding::Base64 => ContentTransferEncoding::Base64,
         }
     }
 
-    /// Returns `true` if using `encoding` to encode this `MaybeString`
-    /// would result into an invalid encoded body.
-    fn is_encoding_ok(&self, encoding: ContentTransferEncoding) -> bool {
-        match encoding {
-            ContentTransferEncoding::SevenBit => is_7bit_encoded(&self),
-            ContentTransferEncoding::EightBit => is_8bit_encoded(&self),
-            ContentTransferEncoding::Binary
-            | ContentTransferEncoding::QuotedPrintable
-            | ContentTransferEncoding::Base64 => true,
+    /// Encode line endings to CRLF if the variant is `String`
+    fn encode_crlf(&mut self) {
+        match self {
+            Self::String(string) => in_place_crlf_line_endings(string),
+            Self::Binary(_) => {}
         }
     }
 }
@@ -187,6 +181,7 @@ impl MaybeString {
 /// **NOTE:** if using the specified `encoding` would result into a malformed
 /// body, this will panic!
 pub trait IntoBody {
+    /// Encode as valid body
     fn into_body(self, encoding: Option<ContentTransferEncoding>) -> Body;
 }
 
@@ -253,76 +248,46 @@ impl Deref for MaybeString {
     }
 }
 
-/// Checks whether it contains only US-ASCII characters,
-/// and no lines are longer than 1000 characters including the `\n` character.
+/// In place conversion to CRLF line endings
+fn in_place_crlf_line_endings(string: &mut String) {
+    let indices = find_all_lf_char_indices(string);
+
+    for i in indices {
+        // this relies on `indices` being in reverse order
+        string.insert(i, '\r');
+    }
+}
+
+/// Find indices to all places where `\r` should be inserted
+/// in order to make `s` have CRLF line endings
 ///
-/// Most efficient content encoding available
-fn is_7bit_encoded(buf: &[u8]) -> bool {
-    buf.is_ascii() && !contains_too_long_lines(buf)
-}
+/// The list is reversed, which is more efficient.
+fn find_all_lf_char_indices(s: &str) -> Vec<usize> {
+    let mut indices = Vec::new();
 
-/// Checks that no lines are longer than 1000 characters,
-/// including the `\n` character.
-/// NOTE: 8bit isn't supported by all SMTP servers.
-fn is_8bit_encoded(buf: &[u8]) -> bool {
-    !contains_too_long_lines(buf)
-}
-
-/// Checks if there are lines that are longer than 1000 characters,
-/// including the `\n` character.
-fn contains_too_long_lines(buf: &[u8]) -> bool {
-    buf.len() > 1000 && buf.split(|&b| b == b'\n').any(|line| line.len() > 999)
-}
-
-const LINE_SEPARATOR: &[u8] = b"\r\n";
-const LINE_MAX_LENGTH: usize = 78 - LINE_SEPARATOR.len();
-
-/// A `Write`r that inserts a line separator `\r\n` every `max_line_length` bytes.
-struct LineWrappingWriter<'a, W> {
-    writer: &'a mut W,
-    current_line_length: usize,
-    max_line_length: usize,
-}
-
-impl<'a, W> LineWrappingWriter<'a, W> {
-    pub fn new(writer: &'a mut W, max_line_length: usize) -> Self {
-        Self {
-            writer,
-            current_line_length: 0,
-            max_line_length,
-        }
-    }
-}
-
-impl<'a, W> Write for LineWrappingWriter<'a, W>
-where
-    W: Write,
-{
-    fn write(&mut self, buf: &[u8]) -> io::Result<usize> {
-        let remaining_line_len = self.max_line_length - self.current_line_length;
-        let write_len = std::cmp::min(buf.len(), remaining_line_len);
-
-        self.writer.write_all(&buf[..write_len])?;
-
-        if remaining_line_len == write_len {
-            self.writer.write_all(LINE_SEPARATOR)?;
-
-            self.current_line_length = 0;
-        } else {
-            self.current_line_length += write_len;
+    let mut found_lf = false;
+    for (i, c) in s.char_indices().rev() {
+        if mem::take(&mut found_lf) && c != '\r' {
+            // the previous character was `\n`, but this isn't a `\r`
+            indices.push(i + c.len_utf8());
         }
 
-        Ok(write_len)
+        found_lf = c == '\n';
     }
 
-    fn flush(&mut self) -> io::Result<()> {
-        self.writer.flush()
+    if found_lf {
+        // the first character is `\n`
+        indices.push(0);
     }
+
+    indices
 }
 
 #[cfg(test)]
 mod test {
-    use super::{Body, ContentTransferEncoding};
+    use pretty_assertions::assert_eq;
+
+    use super::{in_place_crlf_line_endings, Body, ContentTransferEncoding};
 
     #[test]
     fn seven_bit_detect() {
@@ -454,13 +419,10 @@ mod test {
 
     #[test]
     fn quoted_printable_detect() {
-        let encoded = Body::new(String::from("Привет, мир!"));
+        let encoded = Body::new(String::from("Questo messaggio è corto"));
 
         assert_eq!(encoded.encoding(), ContentTransferEncoding::QuotedPrintable);
-        assert_eq!(
-            encoded.as_ref(),
-            b"=D0=9F=D1=80=D0=B8=D0=B2=D0=B5=D1=82, =D0=BC=D0=B8=D1=80!".as_ref()
-        );
+        assert_eq!(encoded.as_ref(), b"Questo messaggio =C3=A8 corto");
     }
 
     #[test]
@@ -492,14 +454,17 @@ mod test {
 
     #[test]
     fn quoted_printable_encode_line_wrap() {
-        let encoded = Body::new(String::from("Текст письма в уникоде"));
+        let encoded = Body::new(String::from(
+            "Se lo standard 📬 fosse stato più semplice avremmo finito molto prima.",
+        ));
 
         assert_eq!(encoded.encoding(), ContentTransferEncoding::QuotedPrintable);
+        println!("{}", std::str::from_utf8(encoded.as_ref()).unwrap());
         assert_eq!(
             encoded.as_ref(),
             concat!(
-                "=D0=A2=D0=B5=D0=BA=D1=81=D1=82 =D0=BF=D0=B8=D1=81=D1=8C=D0=BC=D0=B0 =D0=B2 =\r\n",
-                "=D1=83=D0=BD=D0=B8=D0=BA=D0=BE=D0=B4=D0=B5"
+                "Se lo standard =F0=9F=93=AC fosse stato pi=C3=B9 semplice avremmo finito mo=\r\n",
+                "lto prima."
             )
             .as_bytes()
         );
@@ -507,27 +472,31 @@ mod test {
 
     #[test]
     fn base64_detect() {
-        let input = Body::new(vec![0, 1, 2, 3, 4, 5, 6, 7, 8, 9]);
+        let input = Body::new(vec![0; 80]);
         let encoding = input.encoding();
         assert_eq!(encoding, ContentTransferEncoding::Base64);
     }
 
     #[test]
     fn base64_encode_bytes() {
-        let encoded = Body::new_with_encoding(
-            vec![0, 1, 2, 3, 4, 5, 6, 7, 8, 9],
-            ContentTransferEncoding::Base64,
-        )
-        .unwrap();
+        let encoded =
+            Body::new_with_encoding(vec![0; 80], ContentTransferEncoding::Base64).unwrap();
 
         assert_eq!(encoded.encoding(), ContentTransferEncoding::Base64);
-        assert_eq!(encoded.as_ref(), b"AAECAwQFBgcICQ==");
+        assert_eq!(
+            encoded.as_ref(),
+            concat!(
+                "AAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA\r\n",
+                "AAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA="
+            )
+            .as_bytes()
+        );
     }
 
     #[test]
     fn base64_encode_bytes_wrapping() {
         let encoded = Body::new_with_encoding(
-            vec![0, 1, 2, 3, 4, 5, 6, 7, 8, 9].repeat(20),
+            [0, 1, 2, 3, 4, 5, 6, 7, 8, 9].repeat(20),
             ContentTransferEncoding::Base64,
         )
         .unwrap();
@@ -576,4 +545,31 @@ mod test {
             .as_bytes()
         );
     }
+
+    #[test]
+    fn crlf() {
+        let mut string = String::from("Send me a ✉️\nwith\nlettre!\n😀");
+
+        in_place_crlf_line_endings(&mut string);
+        assert_eq!(string, "Send me a ✉️\r\nwith\r\nlettre!\r\n😀");
+    }
+
+    #[test]
+    fn harsh_crlf() {
+        let mut string = String::from("\n\nSend me a ✉️\r\n\nwith\n\nlettre!\n\r\n😀");
+
+        in_place_crlf_line_endings(&mut string);
+        assert_eq!(
+            string,
+            "\r\n\r\nSend me a ✉️\r\n\r\nwith\r\n\r\nlettre!\r\n\r\n😀"
+        );
+    }
+
+    #[test]
+    fn crlf_noop() {
+        let mut string = String::from("\r\nSend me a ✉️\r\nwith\r\nlettre!\r\n😀");
+
+        in_place_crlf_line_endings(&mut string);
+        assert_eq!(string, "\r\nSend me a ✉️\r\nwith\r\nlettre!\r\n😀");
+    }
 }

src/message/dkim.rs

@@ -0,0 +1,615 @@
+use std::{
+    borrow::Cow,
+    error::Error as StdError,
+    fmt::{self, Display},
+    time::SystemTime,
+};
+
+use ed25519_dalek::Signer;
+use rsa::{pkcs1::DecodeRsaPrivateKey, pkcs1v15::Pkcs1v15Sign, RsaPrivateKey};
+use sha2::{Digest, Sha256};
+
+use crate::message::{
+    header::{HeaderName, HeaderValue},
+    Headers, Message,
+};
+
+/// Describe Dkim Canonicalization to apply to either body or headers
+#[derive(Copy, Clone, Debug)]
+pub enum DkimCanonicalizationType {
+    Simple,
+    Relaxed,
+}
+
+impl Display for DkimCanonicalizationType {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        f.write_str(match self {
+            DkimCanonicalizationType::Simple => "simple",
+            DkimCanonicalizationType::Relaxed => "relaxed",
+        })
+    }
+}
+
+/// Describe Canonicalization to be applied before signing
+#[derive(Copy, Clone, Debug)]
+pub struct DkimCanonicalization {
+    pub header: DkimCanonicalizationType,
+    pub body: DkimCanonicalizationType,
+}
+
+impl Default for DkimCanonicalization {
+    fn default() -> Self {
+        DkimCanonicalization {
+            header: DkimCanonicalizationType::Simple,
+            body: DkimCanonicalizationType::Relaxed,
+        }
+    }
+}
+
+/// Format canonicalization to be shown in Dkim header
+impl Display for DkimCanonicalization {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        write!(f, "{}/{}", self.header, self.body)
+    }
+}
+
+/// Describe the algorithm used for signing the message
+#[derive(Copy, Clone, Debug)]
+pub enum DkimSigningAlgorithm {
+    Rsa,
+    Ed25519,
+}
+
+impl Display for DkimSigningAlgorithm {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        f.write_str(match self {
+            DkimSigningAlgorithm::Rsa => "rsa",
+            DkimSigningAlgorithm::Ed25519 => "ed25519",
+        })
+    }
+}
+
+/// Describe [`DkimSigningKey`] key error
+#[derive(Debug)]
+pub struct DkimSigningKeyError(InnerDkimSigningKeyError);
+
+#[derive(Debug)]
+enum InnerDkimSigningKeyError {
+    Base64(base64::DecodeError),
+    Rsa(rsa::pkcs1::Error),
+    Ed25519(ed25519_dalek::ed25519::Error),
+}
+
+impl Display for DkimSigningKeyError {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        f.write_str(match &self.0 {
+            InnerDkimSigningKeyError::Base64(_err) => "base64 decode error",
+            InnerDkimSigningKeyError::Rsa(_err) => "rsa decode error",
+            InnerDkimSigningKeyError::Ed25519(_err) => "ed25519 decode error",
+        })
+    }
+}
+
+impl StdError for DkimSigningKeyError {
+    fn source(&self) -> Option<&(dyn StdError + 'static)> {
+        Some(match &self.0 {
+            InnerDkimSigningKeyError::Base64(err) => err,
+            InnerDkimSigningKeyError::Rsa(err) => err,
+            InnerDkimSigningKeyError::Ed25519(err) => err,
+        })
+    }
+}
+
+/// Describe a signing key to be carried by [`DkimConfig`] struct
+#[derive(Debug)]
+pub struct DkimSigningKey(InnerDkimSigningKey);
+
+#[derive(Debug)]
+enum InnerDkimSigningKey {
+    Rsa(RsaPrivateKey),
+    Ed25519(ed25519_dalek::SigningKey),
+}
+
+impl DkimSigningKey {
+    pub fn new(
+        private_key: &str,
+        algorithm: DkimSigningAlgorithm,
+    ) -> Result<DkimSigningKey, DkimSigningKeyError> {
+        Ok(Self(match algorithm {
+            DkimSigningAlgorithm::Rsa => InnerDkimSigningKey::Rsa(
+                RsaPrivateKey::from_pkcs1_pem(private_key)
+                    .map_err(|err| DkimSigningKeyError(InnerDkimSigningKeyError::Rsa(err)))?,
+            ),
+            DkimSigningAlgorithm::Ed25519 => {
+                InnerDkimSigningKey::Ed25519(ed25519_dalek::SigningKey::from_bytes(
+                    &crate::base64::decode(private_key)
+                        .map_err(|err| DkimSigningKeyError(InnerDkimSigningKeyError::Base64(err)))?
+                        .try_into()
+                        .map_err(|_| {
+                            DkimSigningKeyError(InnerDkimSigningKeyError::Ed25519(
+                                ed25519_dalek::ed25519::Error::new(),
+                            ))
+                        })?,
+                ))
+            }
+        }))
+    }
+    fn get_signing_algorithm(&self) -> DkimSigningAlgorithm {
+        match self.0 {
+            InnerDkimSigningKey::Rsa(_) => DkimSigningAlgorithm::Rsa,
+            InnerDkimSigningKey::Ed25519(_) => DkimSigningAlgorithm::Ed25519,
+        }
+    }
+}
+
+/// A struct to describe Dkim configuration applied when signing a message
+#[derive(Debug)]
+pub struct DkimConfig {
+    /// The name of the key published in DNS
+    selector: String,
+    /// The domain for which we sign the message
+    domain: String,
+    /// The private key in PKCS1 string format
+    private_key: DkimSigningKey,
+    /// A list of header names to be included in the signature. Signing of more than one
+    /// header with the same name is not supported
+    headers: Vec<HeaderName>,
+    /// The signing algorithm to be used when signing
+    canonicalization: DkimCanonicalization,
+}
+
+impl DkimConfig {
+    /// Create a default signature configuration with a set of headers and "simple/relaxed"
+    /// canonicalization
+    pub fn default_config(
+        selector: String,
+        domain: String,
+        private_key: DkimSigningKey,
+    ) -> DkimConfig {
+        DkimConfig {
+            selector,
+            domain,
+            private_key,
+            headers: vec![
+                HeaderName::new_from_ascii_str("From"),
+                HeaderName::new_from_ascii_str("Subject"),
+                HeaderName::new_from_ascii_str("To"),
+                HeaderName::new_from_ascii_str("Date"),
+            ],
+            canonicalization: DkimCanonicalization {
+                header: DkimCanonicalizationType::Simple,
+                body: DkimCanonicalizationType::Relaxed,
+            },
+        }
+    }
+
+    /// Create a [`DkimConfig`]
+    pub fn new(
+        selector: String,
+        domain: String,
+        private_key: DkimSigningKey,
+        headers: Vec<HeaderName>,
+        canonicalization: DkimCanonicalization,
+    ) -> DkimConfig {
+        DkimConfig {
+            selector,
+            domain,
+            private_key,
+            headers,
+            canonicalization,
+        }
+    }
+}
+
+/// Create a Headers struct with a Dkim-Signature Header created from given parameters
+fn dkim_header_format(
+    config: &DkimConfig,
+    timestamp: u64,
+    headers_list: &str,
+    body_hash: &str,
+    signature: &str,
+) -> Headers {
+    let mut headers = Headers::new();
+    let header_name =
+        dkim_canonicalize_header_tag("DKIM-Signature", config.canonicalization.header);
+    let header_name = HeaderName::new_from_ascii(header_name.into()).unwrap();
+    headers.insert_raw(HeaderValue::new(header_name, format!("v=1; a={signing_algorithm}-sha256; d={domain}; s={selector}; c={canon}; q=dns/txt; t={timestamp}; h={headers_list}; bh={body_hash}; b={signature}",domain=config.domain, selector=config.selector,canon=config.canonicalization,timestamp=timestamp,headers_list=headers_list,body_hash=body_hash,signature=signature,signing_algorithm=config.private_key.get_signing_algorithm())));
+    headers
+}
+
+/// Canonicalize the body of an email
+fn dkim_canonicalize_body(
+    mut body: &[u8],
+    canonicalization: DkimCanonicalizationType,
+) -> Cow<'_, [u8]> {
+    match canonicalization {
+        DkimCanonicalizationType::Simple => {
+            // Remove empty lines at end
+            while body.ends_with(b"\r\n\r\n") {
+                body = &body[..body.len() - 2];
+            }
+            Cow::Borrowed(body)
+        }
+        DkimCanonicalizationType::Relaxed => {
+            let mut out = Vec::with_capacity(body.len());
+            loop {
+                match body {
+                    [b' ' | b'\t', b'\r', b'\n', ..] => {}
+                    [b' ' | b'\t', b' ' | b'\t', ..] => {}
+                    [b' ' | b'\t', ..] => out.push(b' '),
+                    [c, ..] => out.push(*c),
+                    [] => break,
+                }
+                body = &body[1..];
+            }
+            // Remove empty lines at end
+            while out.ends_with(b"\r\n\r\n") {
+                out.truncate(out.len() - 2);
+            }
+            Cow::Owned(out)
+        }
+    }
+}
+
+fn dkim_canonicalize_headers_relaxed(headers: &str) -> String {
+    let mut r = String::with_capacity(headers.len());
+
+    fn skip_whitespace(h: &str) -> &str {
+        match h.as_bytes().first() {
+            Some(b' ' | b'\t') => skip_whitespace(&h[1..]),
+            _ => h,
+        }
+    }
+
+    fn name(h: &str, out: &mut String) {
+        if let Some(name_end) = h.bytes().position(|c| c == b':') {
+            let (name, rest) = h.split_at(name_end + 1);
+            *out += name;
+            // Space after header colon is stripped.
+            value(skip_whitespace(rest), out);
+        } else {
+            // This should never happen.
+            *out += h;
+        }
+    }
+
+    fn value(h: &str, out: &mut String) {
+        match h.as_bytes() {
+            // Continuation lines.
+            [b'\r', b'\n', b' ' | b'\t', ..] => {
+                out.push(' ');
+                value(skip_whitespace(&h[2..]), out);
+            }
+            // End of header.
+            [b'\r', b'\n', ..] => {
+                *out += "\r\n";
+                name(&h[2..], out);
+            }
+            // Sequential whitespace.
+            [b' ' | b'\t', b' ' | b'\t' | b'\r', ..] => value(&h[1..], out),
+            // All whitespace becomes spaces.
+            [b'\t', ..] => {
+                out.push(' ');
+                value(&h[1..], out);
+            }
+            [_, ..] => {
+                let mut chars = h.chars();
+                out.push(chars.next().unwrap());
+                value(chars.as_str(), out);
+            }
+            [] => {}
+        }
+    }
+
+    name(headers, &mut r);
+
+    r
+}
+
+/// Canonicalize header tag
+fn dkim_canonicalize_header_tag(
+    name: &str,
+    canonicalization: DkimCanonicalizationType,
+) -> Cow<'_, str> {
+    match canonicalization {
+        DkimCanonicalizationType::Simple => Cow::Borrowed(name),
+        DkimCanonicalizationType::Relaxed => Cow::Owned(name.to_lowercase()),
+    }
+}
+
+/// Canonicalize signed headers passed as `headers_list` among `mail_headers` using canonicalization
+fn dkim_canonicalize_headers<'a>(
+    headers_list: impl IntoIterator<Item = &'a str>,
+    mail_headers: &Headers,
+    canonicalization: DkimCanonicalizationType,
+) -> String {
+    let mut covered_headers = Headers::new();
+    for name in headers_list {
+        if let Some(h) = mail_headers.find_header(name) {
+            let name = dkim_canonicalize_header_tag(name, canonicalization);
+            covered_headers.insert_raw(HeaderValue::dangerous_new_pre_encoded(
+                HeaderName::new_from_ascii(name.into()).unwrap(),
+                h.get_raw().into(),
+                h.get_encoded().into(),
+            ));
+        }
+    }
+
+    let serialized = covered_headers.to_string();
+
+    match canonicalization {
+        DkimCanonicalizationType::Simple => serialized,
+        DkimCanonicalizationType::Relaxed => dkim_canonicalize_headers_relaxed(&serialized),
+    }
+}
+
+/// Sign with Dkim a message by adding Dkim-Signature header created with configuration expressed by
+/// `dkim_config`
+pub fn dkim_sign(message: &mut Message, dkim_config: &DkimConfig) {
+    dkim_sign_fixed_time(message, dkim_config, crate::time::now());
+}
+
+fn dkim_sign_fixed_time(message: &mut Message, dkim_config: &DkimConfig, timestamp: SystemTime) {
+    let timestamp = timestamp
+        .duration_since(SystemTime::UNIX_EPOCH)
+        .unwrap()
+        .as_secs();
+    let headers = message.headers();
+    let body_hash = Sha256::digest(dkim_canonicalize_body(
+        &message.body_raw(),
+        dkim_config.canonicalization.body,
+    ));
+    let bh = crate::base64::encode(body_hash);
+    let mut signed_headers_list =
+        dkim_config
+            .headers
+            .iter()
+            .fold(String::new(), |mut list, header| {
+                if !list.is_empty() {
+                    list.push(':');
+                }
+
+                list.push_str(header);
+                list
+            });
+    if let DkimCanonicalizationType::Relaxed = dkim_config.canonicalization.header {
+        signed_headers_list.make_ascii_lowercase();
+    }
+    let dkim_header = dkim_header_format(dkim_config, timestamp, &signed_headers_list, &bh, "");
+    let signed_headers = dkim_canonicalize_headers(
+        dkim_config.headers.iter().map(AsRef::as_ref),
+        headers,
+        dkim_config.canonicalization.header,
+    );
+    let canonicalized_dkim_header = dkim_canonicalize_headers(
+        ["DKIM-Signature"],
+        &dkim_header,
+        dkim_config.canonicalization.header,
+    );
+    let mut hashed_headers = Sha256::new();
+    hashed_headers.update(signed_headers.as_bytes());
+    hashed_headers.update(canonicalized_dkim_header.trim_end().as_bytes());
+    let hashed_headers = hashed_headers.finalize();
+    let signature = match &dkim_config.private_key.0 {
+        InnerDkimSigningKey::Rsa(private_key) => crate::base64::encode(
+            private_key
+                .sign(Pkcs1v15Sign::new::<Sha256>(), &hashed_headers)
+                .unwrap(),
+        ),
+        InnerDkimSigningKey::Ed25519(private_key) => {
+            crate::base64::encode(private_key.sign(&hashed_headers).to_bytes())
+        }
+    };
+    let dkim_header = dkim_header_format(
+        dkim_config,
+        timestamp,
+        &signed_headers_list,
+        &bh,
+        &signature,
+    );
+    message.headers.insert_raw(HeaderValue::new(
+        HeaderName::new_from_ascii_str("DKIM-Signature"),
+        dkim_header.get_raw("DKIM-Signature").unwrap().to_owned(),
+    ));
+}
+
+#[cfg(test)]
+mod test {
+    use pretty_assertions::assert_eq;
+
+    use super::{
+        super::{
+            header::{HeaderName, HeaderValue},
+            Header, Message,
+        },
+        dkim_canonicalize_body, dkim_canonicalize_headers, dkim_sign_fixed_time,
+        DkimCanonicalization, DkimCanonicalizationType, DkimConfig, DkimSigningAlgorithm,
+        DkimSigningKey,
+    };
+    use crate::StdError;
+
+    const KEY_RSA: &str = "-----BEGIN RSA PRIVATE KEY-----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+-----END RSA PRIVATE KEY-----";
+
+    #[derive(Clone)]
+    struct TestHeader(String);
+
+    impl Header for TestHeader {
+        fn name() -> HeaderName {
+            HeaderName::new_from_ascii_str("Test")
+        }
+
+        fn parse(s: &str) -> Result<Self, Box<dyn StdError + Send + Sync>> {
+            Ok(Self(s.into()))
+        }
+
+        fn display(&self) -> HeaderValue {
+            HeaderValue::new(Self::name(), self.0.clone())
+        }
+    }
+
+    fn test_message() -> Message {
+        Message::builder()
+            .from("Test O'Leary <test+ezrz@example.net>".parse().unwrap())
+            .to("Test2 <test2@example.org>".parse().unwrap())
+            .date(std::time::UNIX_EPOCH)
+            .header(TestHeader("test  test very very long with spaces and extra spaces   \twill be folded to several lines ".to_owned()))
+            .subject("Test with utf-8 ë")
+            .body("test\r\n\r\ntest   \ttest\r\n\r\n\r\n".to_owned()).unwrap()
+    }
+
+    #[test]
+    fn test_headers_simple_canonicalize() {
+        let message = test_message();
+        dbg!(message.headers.to_string());
+        assert_eq!(dkim_canonicalize_headers(["From", "Test"], &message.headers, DkimCanonicalizationType::Simple), "From: =?utf-8?b?VGVzdCBPJ0xlYXJ5?= <test+ezrz@example.net>\r\nTest: test  test very very long with spaces and extra spaces   \twill be\r\n folded to several lines \r\n");
+    }
+
+    #[test]
+    fn test_headers_relaxed_canonicalize() {
+        let message = test_message();
+        dbg!(message.headers.to_string());
+        assert_eq!(dkim_canonicalize_headers(["From", "Test"], &message.headers, DkimCanonicalizationType::Relaxed),"from:=?utf-8?b?VGVzdCBPJ0xlYXJ5?= <test+ezrz@example.net>\r\ntest:test test very very long with spaces and extra spaces will be folded to several lines\r\n");
+    }
+
+    #[test]
+    fn test_body_simple_canonicalize() {
+        let body = b" C \r\nD \t E\r\n\r\n\r\n";
+        assert_eq!(
+            dkim_canonicalize_body(body, DkimCanonicalizationType::Simple).into_owned(),
+            b" C \r\nD \t E\r\n"
+        );
+    }
+
+    #[test]
+    fn test_body_relaxed_canonicalize() {
+        let body = b" C \r\nD \t E\r\n\tF\r\n\t\r\n\r\n\r\n";
+        assert_eq!(
+            dkim_canonicalize_body(body, DkimCanonicalizationType::Relaxed).into_owned(),
+            b" C\r\nD E\r\n F\r\n"
+        );
+    }
+
+    #[test]
+    fn test_signature_rsa_simple() {
+        let mut message = test_message();
+        let signing_key = DkimSigningKey::new(KEY_RSA, DkimSigningAlgorithm::Rsa).unwrap();
+        dkim_sign_fixed_time(
+            &mut message,
+            &DkimConfig::new(
+                "dkimtest".to_owned(),
+                "example.org".to_owned(),
+                signing_key,
+                vec![
+                    HeaderName::new_from_ascii_str("Date"),
+                    HeaderName::new_from_ascii_str("From"),
+                    HeaderName::new_from_ascii_str("Subject"),
+                    HeaderName::new_from_ascii_str("To"),
+                ],
+                DkimCanonicalization {
+                    header: DkimCanonicalizationType::Simple,
+                    body: DkimCanonicalizationType::Simple,
+                },
+            ),
+            std::time::UNIX_EPOCH,
+        );
+        let signed = message.formatted();
+        let signed = std::str::from_utf8(&signed).unwrap();
+        assert_eq!(
+            signed,
+            std::concat!(
+                "From: =?utf-8?b?VGVzdCBPJ0xlYXJ5?= <test+ezrz@example.net>\r\n",
+                "To: Test2 <test2@example.org>\r\n",
+                "Date: Thu, 01 Jan 1970 00:00:00 +0000\r\n",
+                "Test: test  test very very long with spaces and extra spaces   \twill be\r\n",
+                " folded to several lines \r\n",
+                "Subject: Test with utf-8 =?utf-8?b?w6s=?=\r\n",
+                "Content-Transfer-Encoding: 7bit\r\n",
+                "DKIM-Signature: v=1; a=rsa-sha256; d=example.org; s=dkimtest;\r\n",
+                " c=simple/simple; q=dns/txt; t=0; h=Date:From:Subject:To;\r\n",
+                " bh=f3Zksdcjqa/xRBwdyFzIXWCcgP7XTgxjCgYsXOMKQl4=;\r\n",
+                " b=NhoIMMAALoSgu5lKAR0+MUQunOWnU7wpF9ORUFtpxq9sGZDo9AX43AMhFemyM5W204jpFwMU6pm7AMR1nOYBdSYye4yUALtvT2nqbJBwSh7JeYu+z22t1RFKp7qQR1il8aSrkbZuNMFHYuSEwW76QtKwcNqP4bQOzS9CzgQp0ABu8qwYPBr/EypykPTfqjtyN+ywrfdqjjGOzTpRGolH0hc3CrAETNjjHbNBgKgucXmXTN7hMRdzqWjeFPxizXwouwNAavFClPG0l33gXVArFWn+CkgA84G/s4zuJiF7QPZR87Pu4pw/vIlSXxH4a42W3tT19v9iBTH7X7ldYegtmQ==\r\n",
+                "\r\n",
+                "test\r\n",
+                "\r\n",
+                "test   \ttest\r\n",
+                "\r\n",
+                "\r\n",
+            )
+        );
+    }
+
+    #[test]
+    fn test_signature_rsa_relaxed() {
+        let mut message = test_message();
+        let signing_key = DkimSigningKey::new(KEY_RSA, DkimSigningAlgorithm::Rsa).unwrap();
+        dkim_sign_fixed_time(
+            &mut message,
+            &DkimConfig::new(
+                "dkimtest".to_owned(),
+                "example.org".to_owned(),
+                signing_key,
+                vec![
+                    HeaderName::new_from_ascii_str("Date"),
+                    HeaderName::new_from_ascii_str("From"),
+                    HeaderName::new_from_ascii_str("Subject"),
+                    HeaderName::new_from_ascii_str("To"),
+                ],
+                DkimCanonicalization {
+                    header: DkimCanonicalizationType::Relaxed,
+                    body: DkimCanonicalizationType::Relaxed,
+                },
+            ),
+            std::time::UNIX_EPOCH,
+        );
+        let signed = message.formatted();
+        let signed = std::str::from_utf8(&signed).unwrap();
+        println!("{signed}");
+        assert_eq!(
+            signed,
+            std::concat!(
+                "From: =?utf-8?b?VGVzdCBPJ0xlYXJ5?= <test+ezrz@example.net>\r\n",
+                "To: Test2 <test2@example.org>\r\n",
+                "Date: Thu, 01 Jan 1970 00:00:00 +0000\r\n",
+                "Test: test  test very very long with spaces and extra spaces   \twill be\r\n",
+                " folded to several lines \r\n","Subject: Test with utf-8 =?utf-8?b?w6s=?=\r\n",
+                "Content-Transfer-Encoding: 7bit\r\n",
+                "DKIM-Signature: v=1; a=rsa-sha256; d=example.org; s=dkimtest;\r\n",
+                " c=relaxed/relaxed; q=dns/txt; t=0; h=date:from:subject:to;\r\n",
+                " bh=qN8je6qJgWFGSnN2MycC/XKPbN6BOrMJyAX2h4m19Ss=;\r\n",
+                " b=YaVfmH8dbGEywoLJ4uhbvYqDyQG1UGKFH3PE7zXGgk+YFxUgkwWjoA3aQupDNQtfTjfUsNe0dnrjyZP+ylnESpZBpbCIf5/n3FEh6j3RQthqNbQblcfH/U8mazTuRbVjYBbTZQDaQCMPTz+8D+ZQfXo2oq6dGzTuGvmuYft0CVsq/BIp/EkhZHqiphDeVJSHD4iKW8+L2XwEWThoY92xOYc1G0TtBwz2UJgtiHX2YulH/kRBHeK3dKn9RTNVL3VZ+9ZrnFwIhET9TPGtU2I+q0EMSWF9H9bTrASMgW/U+E0VM2btqJlrTU6rQ7wlQeHdwecLnzXcyhCUInF1+veMNw==\r\n",
+                "\r\n",
+                "test\r\n",
+                "\r\n",
+                "test   \ttest\r\n",
+                "\r\n",
+                "\r\n",
+            )
+        );
+    }
+}

src/message/header/content.rs

@@ -1,32 +1,45 @@
-use hyperx::{
-    header::{Formatter as HeaderFormatter, Header, RawLike},
-    Error as HeaderError, Result as HyperResult,
-};
 use std::{
     fmt::{Display, Formatter as FmtFormatter, Result as FmtResult},
-    str::{from_utf8, FromStr},
+    str::FromStr,
 };
 
-header! { (ContentId, "Content-ID") => [String] }
+use super::{Header, HeaderName, HeaderValue};
+use crate::BoxError;
 
 /// `Content-Transfer-Encoding` of the body
 ///
 /// The `Message` builder takes care of choosing the most
 /// efficient encoding based on the chosen body, so in most
 /// use-caches this header shouldn't be set manually.
-#[derive(Debug, Clone, Copy, PartialEq)]
+#[derive(Debug, Clone, Copy, PartialEq, Eq, Hash)]
+#[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
+#[derive(Default)]
 pub enum ContentTransferEncoding {
+    /// ASCII
     SevenBit,
+    /// Quoted-Printable encoding
     QuotedPrintable,
+    /// base64 encoding
+    #[default]
     Base64,
-    // 8BITMIME
+    /// Requires `8BITMIME`
     EightBit,
+    /// Binary data
     Binary,
 }
 
-impl Default for ContentTransferEncoding {
-    fn default() -> Self {
-        ContentTransferEncoding::Base64
+impl Header for ContentTransferEncoding {
+    fn name() -> HeaderName {
+        HeaderName::new_from_ascii_str("Content-Transfer-Encoding")
+    }
+
+    fn parse(s: &str) -> Result<Self, BoxError> {
+        Ok(s.parse()?)
+    }
+
+    fn display(&self) -> HeaderValue {
+        let val = self.to_string();
+        HeaderValue::dangerous_new_pre_encoded(Self::name(), val.clone(), val)
     }
 }
 
@@ -56,35 +69,12 @@ impl FromStr for ContentTransferEncoding {
     }
 }
 
-impl Header for ContentTransferEncoding {
-    fn header_name() -> &'static str {
-        "Content-Transfer-Encoding"
-    }
-
-    // FIXME HeaderError->HeaderError, same for result
-    fn parse_header<'a, T>(raw: &'a T) -> HyperResult<Self>
-    where
-        T: RawLike<'a>,
-        Self: Sized,
-    {
-        raw.one()
-            .ok_or(HeaderError::Header)
-            .and_then(|r| from_utf8(r).map_err(|_| HeaderError::Header))
-            .and_then(|s| {
-                s.parse::<ContentTransferEncoding>()
-                    .map_err(|_| HeaderError::Header)
-            })
-    }
-
-    fn fmt_header(&self, f: &mut HeaderFormatter<'_, '_>) -> FmtResult {
-        f.fmt_line(&format!("{}", self))
-    }
-}
-
 #[cfg(test)]
 mod test {
+    use pretty_assertions::assert_eq;
+
     use super::ContentTransferEncoding;
-    use hyperx::header::Headers;
+    use crate::message::header::{HeaderName, HeaderValue, Headers};
 
     #[test]
     fn format_content_transfer_encoding() {
@@ -92,35 +82,35 @@ mod test {
 
         headers.set(ContentTransferEncoding::SevenBit);
 
-        assert_eq!(
-            format!("{}", headers),
-            "Content-Transfer-Encoding: 7bit\r\n"
-        );
+        assert_eq!(headers.to_string(), "Content-Transfer-Encoding: 7bit\r\n");
 
         headers.set(ContentTransferEncoding::Base64);
 
-        assert_eq!(
-            format!("{}", headers),
-            "Content-Transfer-Encoding: base64\r\n"
-        );
+        assert_eq!(headers.to_string(), "Content-Transfer-Encoding: base64\r\n");
     }
 
     #[test]
     fn parse_content_transfer_encoding() {
         let mut headers = Headers::new();
 
-        headers.set_raw("Content-Transfer-Encoding", "7bit");
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("Content-Transfer-Encoding"),
+            "7bit".to_owned(),
+        ));
 
         assert_eq!(
             headers.get::<ContentTransferEncoding>(),
-            Some(&ContentTransferEncoding::SevenBit)
+            Some(ContentTransferEncoding::SevenBit)
         );
 
-        headers.set_raw("Content-Transfer-Encoding", "base64");
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("Content-Transfer-Encoding"),
+            "base64".to_owned(),
+        ));
 
         assert_eq!(
             headers.get::<ContentTransferEncoding>(),
-            Some(&ContentTransferEncoding::Base64)
+            Some(ContentTransferEncoding::Base64)
         );
     }
 }

src/message/header/content_disposition.rs

@@ -0,0 +1,127 @@
+use std::fmt::Write;
+
+use email_encoding::headers::writer::EmailWriter;
+
+use super::{Header, HeaderName, HeaderValue};
+use crate::BoxError;
+
+/// `Content-Disposition` of an attachment
+///
+/// Defined in [RFC2183](https://tools.ietf.org/html/rfc2183)
+#[derive(Debug, Clone, PartialEq)]
+pub struct ContentDisposition(HeaderValue);
+
+impl ContentDisposition {
+    /// An attachment which should be displayed inline into the message
+    pub fn inline() -> Self {
+        Self(HeaderValue::dangerous_new_pre_encoded(
+            Self::name(),
+            "inline".to_owned(),
+            "inline".to_owned(),
+        ))
+    }
+
+    /// An attachment which should be displayed inline into the message, but that also
+    /// species the filename in case it is downloaded
+    pub fn inline_with_name(file_name: &str) -> Self {
+        Self::with_name("inline", file_name)
+    }
+
+    /// An attachment which is separate from the body of the message, and can be downloaded separately
+    pub fn attachment(file_name: &str) -> Self {
+        Self::with_name("attachment", file_name)
+    }
+
+    fn with_name(kind: &str, file_name: &str) -> Self {
+        let raw_value = format!("{kind}; filename=\"{file_name}\"");
+
+        let mut encoded_value = String::new();
+        let line_len = "Content-Disposition: ".len();
+        {
+            let mut w = EmailWriter::new(&mut encoded_value, line_len, 0, false);
+            w.write_str(kind).expect("writing `kind` returned an error");
+            w.write_char(';').expect("writing `;` returned an error");
+            w.space();
+
+            email_encoding::headers::rfc2231::encode("filename", file_name, &mut w)
+                .expect("some Write implementation returned an error");
+        }
+
+        Self(HeaderValue::dangerous_new_pre_encoded(
+            Self::name(),
+            raw_value,
+            encoded_value,
+        ))
+    }
+}
+
+impl Header for ContentDisposition {
+    fn name() -> HeaderName {
+        HeaderName::new_from_ascii_str("Content-Disposition")
+    }
+
+    fn parse(s: &str) -> Result<Self, BoxError> {
+        match (s.split_once(';'), s) {
+            (_, "inline") => Ok(Self::inline()),
+            (Some((kind @ ("inline" | "attachment"), file_name)), _) => file_name
+                .split_once(" filename=\"")
+                .and_then(|(_, file_name)| file_name.strip_suffix('"'))
+                .map(|file_name| Self::with_name(kind, file_name))
+                .ok_or_else(|| "Unsupported ContentDisposition value".into()),
+            _ => Err("Unsupported ContentDisposition value".into()),
+        }
+    }
+
+    fn display(&self) -> HeaderValue {
+        self.0.clone()
+    }
+}
+
+#[cfg(test)]
+mod test {
+    use pretty_assertions::assert_eq;
+
+    use super::ContentDisposition;
+    use crate::message::header::{HeaderName, HeaderValue, Headers};
+
+    #[test]
+    fn format_content_disposition() {
+        let mut headers = Headers::new();
+
+        headers.set(ContentDisposition::inline());
+
+        assert_eq!(format!("{headers}"), "Content-Disposition: inline\r\n");
+
+        headers.set(ContentDisposition::attachment("something.txt"));
+
+        assert_eq!(
+            format!("{headers}"),
+            "Content-Disposition: attachment; filename=\"something.txt\"\r\n"
+        );
+    }
+
+    #[test]
+    fn parse_content_disposition() {
+        let mut headers = Headers::new();
+
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("Content-Disposition"),
+            "inline".to_owned(),
+        ));
+
+        assert_eq!(
+            headers.get::<ContentDisposition>(),
+            Some(ContentDisposition::inline())
+        );
+
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("Content-Disposition"),
+            "attachment; filename=\"something.txt\"".to_owned(),
+        ));
+
+        assert_eq!(
+            headers.get::<ContentDisposition>(),
+            Some(ContentDisposition::attachment("something.txt"))
+        );
+    }
+}

src/message/header/content_type.rs

@@ -0,0 +1,193 @@
+use std::{
+    error::Error as StdError,
+    fmt::{self, Display},
+    str::FromStr,
+};
+
+use mime::Mime;
+
+use super::{Header, HeaderName, HeaderValue};
+use crate::BoxError;
+
+/// `Content-Type` of the body
+///
+/// This struct can represent any valid [MIME type], which can be parsed via
+/// [`ContentType::parse`]. Constants are provided for the most-used mime-types.
+///
+/// Defined in [RFC2045](https://tools.ietf.org/html/rfc2045#section-5)
+///
+/// [MIME type]: https://www.iana.org/assignments/media-types/media-types.xhtml
+#[derive(Debug, Clone, PartialEq, Eq)]
+pub struct ContentType(Mime);
+
+impl ContentType {
+    /// A `ContentType` of type `text/plain; charset=utf-8`
+    ///
+    /// Indicates that the body is in utf-8 encoded plain text.
+    pub const TEXT_PLAIN: ContentType = Self::from_mime(mime::TEXT_PLAIN_UTF_8);
+
+    /// A `ContentType` of type `text/html; charset=utf-8`
+    ///
+    /// Indicates that the body is in utf-8 encoded html.
+    pub const TEXT_HTML: ContentType = Self::from_mime(mime::TEXT_HTML_UTF_8);
+
+    /// Parse `s` into `ContentType`
+    pub fn parse(s: &str) -> Result<ContentType, ContentTypeErr> {
+        Ok(Self::from_mime(s.parse().map_err(ContentTypeErr)?))
+    }
+
+    pub(crate) const fn from_mime(mime: Mime) -> Self {
+        Self(mime)
+    }
+
+    pub(crate) fn as_ref(&self) -> &Mime {
+        &self.0
+    }
+}
+
+impl Header for ContentType {
+    fn name() -> HeaderName {
+        HeaderName::new_from_ascii_str("Content-Type")
+    }
+
+    fn parse(s: &str) -> Result<Self, BoxError> {
+        Ok(Self(s.parse()?))
+    }
+
+    fn display(&self) -> HeaderValue {
+        HeaderValue::new(Self::name(), self.0.to_string())
+    }
+}
+
+impl FromStr for ContentType {
+    type Err = ContentTypeErr;
+
+    fn from_str(s: &str) -> Result<Self, Self::Err> {
+        Self::parse(s)
+    }
+}
+
+#[cfg(feature = "mime03")]
+#[cfg_attr(docsrs, doc(cfg(feature = "mime03")))]
+impl From<Mime> for ContentType {
+    fn from(mime: Mime) -> Self {
+        Self::from_mime(mime)
+    }
+}
+
+/// An error occurred while trying to [`ContentType::parse`].
+#[derive(Debug)]
+pub struct ContentTypeErr(mime::FromStrError);
+
+impl StdError for ContentTypeErr {
+    fn source(&self) -> Option<&(dyn StdError + 'static)> {
+        Some(&self.0)
+    }
+}
+
+impl Display for ContentTypeErr {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        Display::fmt(&self.0, f)
+    }
+}
+
+// -- Serialization and Deserialization --
+#[cfg(feature = "serde")]
+mod serde {
+    use std::fmt;
+
+    use serde::{
+        de::{self, Deserialize, Deserializer, Visitor},
+        ser::{Serialize, Serializer},
+    };
+
+    use super::ContentType;
+
+    impl Serialize for ContentType {
+        fn serialize<S>(&self, serializer: S) -> Result<S::Ok, S::Error>
+        where
+            S: Serializer,
+        {
+            serializer.serialize_newtype_struct("ContentType", &format!("{}", &self.0))
+        }
+    }
+
+    impl<'de> Deserialize<'de> for ContentType {
+        fn deserialize<D>(deserializer: D) -> Result<Self, D::Error>
+        where
+            D: Deserializer<'de>,
+        {
+            struct ContentTypeVisitor;
+
+            impl Visitor<'_> for ContentTypeVisitor {
+                type Value = ContentType;
+
+                // The error message which states what the Visitor expects to
+                // receive
+                fn expecting(&self, formatter: &mut fmt::Formatter<'_>) -> fmt::Result {
+                    formatter.write_str("a ContentType string like `text/plain`")
+                }
+
+                fn visit_str<E>(self, mime: &str) -> Result<ContentType, E>
+                where
+                    E: de::Error,
+                {
+                    match ContentType::parse(mime) {
+                        Ok(content_type) => Ok(content_type),
+                        Err(_) => Err(E::custom(format!(
+                            "Couldn't parse the following MIME-Type: {mime}"
+                        ))),
+                    }
+                }
+            }
+
+            deserializer.deserialize_str(ContentTypeVisitor)
+        }
+    }
+}
+
+#[cfg(test)]
+mod test {
+    use pretty_assertions::assert_eq;
+
+    use super::ContentType;
+    use crate::message::header::{HeaderName, HeaderValue, Headers};
+
+    #[test]
+    fn format_content_type() {
+        let mut headers = Headers::new();
+
+        headers.set(ContentType::TEXT_PLAIN);
+
+        assert_eq!(
+            headers.to_string(),
+            "Content-Type: text/plain; charset=utf-8\r\n"
+        );
+
+        headers.set(ContentType::TEXT_HTML);
+
+        assert_eq!(
+            headers.to_string(),
+            "Content-Type: text/html; charset=utf-8\r\n"
+        );
+    }
+
+    #[test]
+    fn parse_content_type() {
+        let mut headers = Headers::new();
+
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("Content-Type"),
+            "text/plain; charset=utf-8".to_owned(),
+        ));
+
+        assert_eq!(headers.get::<ContentType>(), Some(ContentType::TEXT_PLAIN));
+
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("Content-Type"),
+            "text/html; charset=utf-8".to_owned(),
+        ));
+
+        assert_eq!(headers.get::<ContentType>(), Some(ContentType::TEXT_HTML));
+    }
+}

src/message/header/date.rs

@@ -0,0 +1,135 @@
+use std::time::SystemTime;
+
+use httpdate::HttpDate;
+
+use super::{Header, HeaderName, HeaderValue};
+use crate::BoxError;
+
+/// Message `Date` header
+///
+/// Defined in [RFC2822](https://tools.ietf.org/html/rfc2822#section-3.3)
+#[derive(Debug, Clone, Copy, PartialEq, Eq)]
+pub struct Date(HttpDate);
+
+impl Date {
+    /// Build a `Date` from [`SystemTime`]
+    pub fn new(st: SystemTime) -> Self {
+        Self(st.into())
+    }
+
+    /// Get the current date
+    ///
+    /// Shortcut for `Date::new(SystemTime::now())`
+    pub fn now() -> Self {
+        Self::new(crate::time::now())
+    }
+}
+
+impl Header for Date {
+    fn name() -> HeaderName {
+        HeaderName::new_from_ascii_str("Date")
+    }
+
+    fn parse(s: &str) -> Result<Self, BoxError> {
+        let mut s = String::from(s);
+        if s.ends_with("+0000") {
+            // The httpdate crate expects the `Date` to end in ` GMT`, but email
+            // uses `+0000` to indicate UTC, so we crudely fix this issue here.
+
+            s.truncate(s.len() - "+0000".len());
+            s.push_str("GMT");
+        }
+
+        Ok(Self(s.parse::<HttpDate>()?))
+    }
+
+    fn display(&self) -> HeaderValue {
+        let mut val = self.0.to_string();
+        if val.ends_with(" GMT") {
+            // The httpdate crate always appends ` GMT` to the end of the string,
+            // but this is considered an obsolete date format for email
+            // https://tools.ietf.org/html/rfc2822#appendix-A.6.2,
+            // so we replace `GMT` with `+0000`
+            val.truncate(val.len() - "GMT".len());
+            val.push_str("+0000");
+        }
+
+        HeaderValue::dangerous_new_pre_encoded(Self::name(), val.clone(), val)
+    }
+}
+
+impl From<SystemTime> for Date {
+    fn from(st: SystemTime) -> Self {
+        Self::new(st)
+    }
+}
+
+impl From<Date> for SystemTime {
+    fn from(this: Date) -> SystemTime {
+        this.0.into()
+    }
+}
+
+#[cfg(test)]
+mod test {
+    use std::time::{Duration, SystemTime};
+
+    use pretty_assertions::assert_eq;
+
+    use super::Date;
+    use crate::message::header::{HeaderName, HeaderValue, Headers};
+
+    #[test]
+    fn format_date() {
+        let mut headers = Headers::new();
+
+        // Tue, 15 Nov 1994 08:12:31 GMT
+        headers.set(Date::from(
+            SystemTime::UNIX_EPOCH + Duration::from_secs(784887151),
+        ));
+
+        assert_eq!(
+            headers.to_string(),
+            "Date: Tue, 15 Nov 1994 08:12:31 +0000\r\n".to_owned()
+        );
+
+        // Tue, 15 Nov 1994 08:12:32 GMT
+        headers.set(Date::from(
+            SystemTime::UNIX_EPOCH + Duration::from_secs(784887152),
+        ));
+
+        assert_eq!(
+            headers.to_string(),
+            "Date: Tue, 15 Nov 1994 08:12:32 +0000\r\n"
+        );
+    }
+
+    #[test]
+    fn parse_date() {
+        let mut headers = Headers::new();
+
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("Date"),
+            "Tue, 15 Nov 1994 08:12:31 +0000".to_owned(),
+        ));
+
+        assert_eq!(
+            headers.get::<Date>(),
+            Some(Date::from(
+                SystemTime::UNIX_EPOCH + Duration::from_secs(784887151),
+            ))
+        );
+
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("Date"),
+            "Tue, 15 Nov 1994 08:12:32 +0000".to_owned(),
+        ));
+
+        assert_eq!(
+            headers.get::<Date>(),
+            Some(Date::from(
+                SystemTime::UNIX_EPOCH + Duration::from_secs(784887152),
+            ))
+        );
+    }
+}

src/message/header/mailbox.rs

@@ -1,12 +1,10 @@
-use crate::message::{
-    mailbox::{Mailbox, Mailboxes},
-    utf8_b,
+use email_encoding::headers::writer::EmailWriter;
+
+use super::{Header, HeaderName, HeaderValue};
+use crate::{
+    message::mailbox::{Mailbox, Mailboxes},
+    BoxError,
 };
-use hyperx::{
-    header::{Formatter as HeaderFormatter, Header, RawLike},
-    Error as HeaderError, Result as HyperResult,
-};
-use std::{fmt::Result as FmtResult, slice::Iter, str::from_utf8};
 
 /// Header which can contains multiple mailboxes
 pub trait MailboxesHeader {
@@ -16,27 +14,42 @@ pub trait MailboxesHeader {
 macro_rules! mailbox_header {
     ($(#[$doc:meta])*($type_name: ident, $header_name: expr)) => {
         $(#[$doc])*
-        #[derive(Debug, Clone, PartialEq)]
-        pub struct $type_name(pub Mailbox);
+        #[derive(Debug, Clone, PartialEq, Eq)]
+        pub struct $type_name(Mailbox);
 
         impl Header for $type_name {
-            fn header_name() -> &'static str {
-                $header_name
+            fn name() -> HeaderName {
+                HeaderName::new_from_ascii_str($header_name)
             }
 
-            fn parse_header<'a, T>(raw: &'a T) -> HyperResult<Self> where
-    T: RawLike<'a>,
-    Self: Sized {
-                raw.one()
-                    .ok_or(HeaderError::Header)
-                    .and_then(parse_mailboxes)
-                    .and_then(|mbs| {
-                        mbs.into_single().ok_or(HeaderError::Header)
-                    }).map($type_name)
+            fn parse(s: &str) -> Result<Self, BoxError> {
+                let mailbox: Mailbox = s.parse()?;
+                Ok(Self(mailbox))
             }
 
-            fn fmt_header(&self, f: &mut HeaderFormatter<'_, '_>) -> FmtResult {
-                f.fmt_line(&self.0.recode_name(utf8_b::encode))
+            fn display(&self) -> HeaderValue {
+                let mut encoded_value = String::new();
+                let line_len = $header_name.len() + ": ".len();
+                {
+                    let mut w = EmailWriter::new(&mut encoded_value, line_len, 0, false);
+                    self.0.encode(&mut w).expect("writing `Mailbox` returned an error");
+                }
+
+                HeaderValue::dangerous_new_pre_encoded(Self::name(), self.0.to_string(), encoded_value)
+            }
+        }
+
+        impl std::convert::From<Mailbox> for $type_name {
+            #[inline]
+            fn from(mailbox: Mailbox) -> Self {
+                Self(mailbox)
+            }
+        }
+
+        impl std::convert::From<$type_name> for Mailbox {
+            #[inline]
+            fn from(this: $type_name) -> Mailbox {
+                this.0
             }
         }
     };
@@ -45,8 +58,8 @@ macro_rules! mailbox_header {
 macro_rules! mailboxes_header {
     ($(#[$doc:meta])*($type_name: ident, $header_name: expr)) => {
         $(#[$doc])*
-        #[derive(Debug, Clone, PartialEq)]
-        pub struct $type_name(pub Mailboxes);
+        #[derive(Debug, Clone, PartialEq, Eq)]
+        pub struct $type_name(pub(crate) Mailboxes);
 
         impl MailboxesHeader for $type_name {
             fn join_mailboxes(&mut self, other: Self) {
@@ -55,23 +68,38 @@ macro_rules! mailboxes_header {
         }
 
         impl Header for $type_name {
-            fn header_name() -> &'static str {
-                $header_name
+            fn name() -> HeaderName {
+                HeaderName::new_from_ascii_str($header_name)
             }
 
-            fn parse_header<'a, T>(raw: &'a T) -> HyperResult<$type_name>
-            where
-                T: RawLike<'a>,
-                Self: Sized,
-            {
-                raw.one()
-                    .ok_or(HeaderError::Header)
-                    .and_then(parse_mailboxes)
-                    .map($type_name)
+            fn parse(s: &str) -> Result<Self, BoxError> {
+                let mailbox: Mailboxes = s.parse()?;
+                Ok(Self(mailbox))
             }
 
-            fn fmt_header(&self, f: &mut HeaderFormatter<'_, '_>) -> FmtResult {
-                format_mailboxes(self.0.iter(), f)
+            fn display(&self) -> HeaderValue {
+                let mut encoded_value = String::new();
+                let line_len = $header_name.len() + ": ".len();
+                {
+                    let mut w = EmailWriter::new(&mut encoded_value, line_len, 0, false);
+                    self.0.encode(&mut w).expect("writing `Mailboxes` returned an error");
+                }
+
+                HeaderValue::dangerous_new_pre_encoded(Self::name(), self.0.to_string(), encoded_value)
+            }
+        }
+
+        impl std::convert::From<Mailboxes> for $type_name {
+            #[inline]
+            fn from(mailboxes: Mailboxes) -> Self {
+                Self(mailboxes)
+            }
+        }
+
+        impl std::convert::From<$type_name> for Mailboxes {
+            #[inline]
+            fn from(this: $type_name) -> Mailboxes {
+                this.0
             }
         }
     };
@@ -82,7 +110,7 @@ mailbox_header! {
 
     `Sender` header
 
-    This header contains [`Mailbox`][self::Mailbox] associated with sender.
+    This header contains [`Mailbox`] associated with sender.
 
     ```no_test
     header::Sender("Mr. Sender <sender@example.com>".parse().unwrap())
@@ -96,7 +124,7 @@ mailboxes_header! {
 
     `From` header
 
-    This header contains [`Mailboxes`][self::Mailboxes].
+    This header contains [`Mailboxes`].
 
      */
     (From, "From")
@@ -107,7 +135,7 @@ mailboxes_header! {
 
     `Reply-To` header
 
-    This header contains [`Mailboxes`][self::Mailboxes].
+    This header contains [`Mailboxes`].
 
      */
     (ReplyTo, "Reply-To")
@@ -118,7 +146,7 @@ mailboxes_header! {
 
     `To` header
 
-    This header contains [`Mailboxes`][self::Mailboxes].
+    This header contains [`Mailboxes`].
 
      */
     (To, "To")
@@ -129,7 +157,7 @@ mailboxes_header! {
 
     `Cc` header
 
-    This header contains [`Mailboxes`][self::Mailboxes].
+    This header contains [`Mailboxes`].
 
      */
     (Cc, "Cc")
@@ -140,32 +168,18 @@ mailboxes_header! {
 
     `Bcc` header
 
-    This header contains [`Mailboxes`][self::Mailboxes].
+    This header contains [`Mailboxes`].
 
      */
     (Bcc, "Bcc")
 }
 
-fn parse_mailboxes(raw: &[u8]) -> HyperResult<Mailboxes> {
-    if let Ok(src) = from_utf8(raw) {
-        if let Ok(mbs) = src.parse() {
-            return Ok(mbs);
-        }
-    }
-    Err(HeaderError::Header)
-}
-
-fn format_mailboxes<'a>(mbs: Iter<'a, Mailbox>, f: &mut HeaderFormatter<'_, '_>) -> FmtResult {
-    f.fmt_line(&Mailboxes::from(
-        mbs.map(|mb| mb.recode_name(utf8_b::encode))
-            .collect::<Vec<_>>(),
-    ))
-}
-
 #[cfg(test)]
 mod test {
+    use pretty_assertions::assert_eq;
+
     use super::{From, Mailbox, Mailboxes};
-    use hyperx::header::Headers;
+    use crate::message::header::{HeaderName, HeaderValue, Headers};
 
     #[test]
     fn format_single_without_name() {
@@ -174,17 +188,17 @@ mod test {
         let mut headers = Headers::new();
         headers.set(From(from));
 
-        assert_eq!(format!("{}", headers), "From: kayo@example.com\r\n");
+        assert_eq!(headers.to_string(), "From: kayo@example.com\r\n");
     }
 
     #[test]
     fn format_single_with_name() {
-        let from = Mailboxes::new().with("K. <kayo@example.com>".parse().unwrap());
+        let from = Mailboxes::new().with("Kayo <kayo@example.com>".parse().unwrap());
 
         let mut headers = Headers::new();
         headers.set(From(from));
 
-        assert_eq!(format!("{}", headers), "From: K. <kayo@example.com>\r\n");
+        assert_eq!(headers.to_string(), "From: Kayo <kayo@example.com>\r\n");
     }
 
     #[test]
@@ -197,7 +211,7 @@ mod test {
         headers.set(From(from));
 
         assert_eq!(
-            format!("{}", headers),
+            headers.to_string(),
             "From: kayo@example.com, pony@domain.tld\r\n"
         );
     }
@@ -205,7 +219,7 @@ mod test {
     #[test]
     fn format_multi_with_name() {
         let from = vec![
-            "K. <kayo@example.com>".parse().unwrap(),
+            "Kayo <kayo@example.com>".parse().unwrap(),
             "Pony P. <pony@domain.tld>".parse().unwrap(),
         ];
 
@@ -213,8 +227,8 @@ mod test {
         headers.set(From(from.into()));
 
         assert_eq!(
-            format!("{}", headers),
-            "From: K. <kayo@example.com>, Pony P. <pony@domain.tld>\r\n"
+            headers.to_string(),
+            "From: Kayo <kayo@example.com>, \"Pony P.\" <pony@domain.tld>\r\n"
         );
     }
 
@@ -226,7 +240,7 @@ mod test {
         headers.set(From(from.into()));
 
         assert_eq!(
-            format!("{}", headers),
+            headers.to_string(),
             "From: =?utf-8?b?0JrQsNC50L4=?= <kayo@example.com>\r\n"
         );
     }
@@ -236,9 +250,12 @@ mod test {
         let from = vec!["kayo@example.com".parse().unwrap()].into();
 
         let mut headers = Headers::new();
-        headers.set_raw("From", "kayo@example.com");
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("From"),
+            "kayo@example.com".to_owned(),
+        ));
 
-        assert_eq!(headers.get::<From>(), Some(&From(from)));
+        assert_eq!(headers.get::<From>(), Some(From(from)));
     }
 
     #[test]
@@ -246,9 +263,12 @@ mod test {
         let from = vec!["K. <kayo@example.com>".parse().unwrap()].into();
 
         let mut headers = Headers::new();
-        headers.set_raw("From", "K. <kayo@example.com>");
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("From"),
+            "K. <kayo@example.com>".to_owned(),
+        ));
 
-        assert_eq!(headers.get::<From>(), Some(&From(from)));
+        assert_eq!(headers.get::<From>(), Some(From(from)));
     }
 
     #[test]
@@ -259,9 +279,12 @@ mod test {
         ];
 
         let mut headers = Headers::new();
-        headers.set_raw("From", "kayo@example.com, pony@domain.tld");
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("From"),
+            "kayo@example.com, pony@domain.tld".to_owned(),
+        ));
 
-        assert_eq!(headers.get::<From>(), Some(&From(from.into())));
+        assert_eq!(headers.get::<From>(), Some(From(from.into())));
     }
 
     #[test]
@@ -272,18 +295,65 @@ mod test {
         ];
 
         let mut headers = Headers::new();
-        headers.set_raw("From", "K. <kayo@example.com>, Pony P. <pony@domain.tld>");
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("From"),
+            "K. <kayo@example.com>, Pony P. <pony@domain.tld>".to_owned(),
+        ));
 
-        assert_eq!(headers.get::<From>(), Some(&From(from.into())));
+        assert_eq!(headers.get::<From>(), Some(From(from.into())));
     }
 
     #[test]
-    fn parse_single_with_utf8_name() {
-        let from: Vec<Mailbox> = vec!["Кайо <kayo@example.com>".parse().unwrap()];
+    fn parse_multi_with_name_containing_comma() {
+        let from: Vec<Mailbox> = vec![
+            "\"Test, test\" <1@example.com>".parse().unwrap(),
+            "\"Test2, test2\" <2@example.com>".parse().unwrap(),
+        ];
 
         let mut headers = Headers::new();
-        headers.set_raw("From", "=?utf-8?b?0JrQsNC50L4=?= <kayo@example.com>");
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("From"),
+            "\"Test, test\" <1@example.com>, \"Test2, test2\" <2@example.com>".to_owned(),
+        ));
 
-        assert_eq!(headers.get::<From>(), Some(&From(from.into())));
+        assert_eq!(headers.get::<From>(), Some(From(from.into())));
+    }
+
+    #[test]
+    fn parse_multi_with_name_containing_double_quotes() {
+        let from: Vec<Mailbox> = vec![
+            "\"Test, test\" <1@example.com>".parse().unwrap(),
+            "\"Test2, \"test2\"\" <2@example.com>".parse().unwrap(),
+        ];
+
+        let mut headers = Headers::new();
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("From"),
+            "\"Test, test\" <1@example.com>, \"Test2, \"test2\"\" <2@example.com>".to_owned(),
+        ));
+
+        assert_eq!(headers.get::<From>(), Some(From(from.into())));
+    }
+
+    #[test]
+    fn parse_multi_with_name_containing_comma_last_broken() {
+        let mut headers = Headers::new();
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("From"),
+            "\"Test, test\" <1@example.com>, \"Test2, test2\"".to_owned(),
+        ));
+
+        assert_eq!(headers.get::<From>(), None);
+    }
+
+    #[test]
+    fn mailbox_format_address_with_angle_bracket() {
+        assert_eq!(
+            format!(
+                "{}",
+                Mailbox::new(Some("<3".into()), "i@love.example".parse().unwrap())
+            ),
+            r#""<3" <i@love.example>"#
+        );
     }
 }

src/message/header/mod.rs

@@ -1,17 +1,754 @@
-/*!
+//! Headers widely used in email messages
 
-## Headers widely used in email messages
+use std::{
+    borrow::Cow,
+    error::Error,
+    fmt::{self, Display, Formatter, Write},
+    ops::Deref,
+};
 
-*/
+use email_encoding::headers::writer::EmailWriter;
+
+pub use self::{
+    content::*,
+    content_disposition::ContentDisposition,
+    content_type::{ContentType, ContentTypeErr},
+    date::Date,
+    mailbox::*,
+    special::*,
+    textual::*,
+};
+use crate::BoxError;
 
 mod content;
+mod content_disposition;
+mod content_type;
+mod date;
 mod mailbox;
 mod special;
 mod textual;
 
-pub use self::{content::*, mailbox::*, special::*, textual::*};
+/// Represents an email header
+///
+/// Email header as defined in [RFC5322](https://datatracker.ietf.org/doc/html/rfc5322) and extensions.
+pub trait Header: Clone {
+    fn name() -> HeaderName;
 
-pub use hyperx::header::{
-    Charset, ContentDisposition, ContentLocation, ContentType, Date, DispositionParam,
-    DispositionType, Header, Headers, HttpDate as EmailDate,
-};
+    fn parse(s: &str) -> Result<Self, BoxError>;
+
+    fn display(&self) -> HeaderValue;
+}
+
+/// A set of email headers
+#[derive(Debug, Clone, Default)]
+pub struct Headers {
+    headers: Vec<HeaderValue>,
+}
+
+impl Headers {
+    /// Create an empty `Headers`
+    ///
+    /// This function does not allocate.
+    #[inline]
+    pub const fn new() -> Self {
+        Self {
+            headers: Vec::new(),
+        }
+    }
+
+    /// Create an empty `Headers` with a pre-allocated capacity
+    ///
+    /// Pre-allocates a capacity of at least `capacity`.
+    #[inline]
+    pub fn with_capacity(capacity: usize) -> Self {
+        Self {
+            headers: Vec::with_capacity(capacity),
+        }
+    }
+
+    /// Returns a copy of a `Header` present in `Headers`
+    ///
+    /// Returns `None` if `Header` isn't present in `Headers`.
+    pub fn get<H: Header>(&self) -> Option<H> {
+        self.get_raw(&H::name())
+            .and_then(|raw_value| H::parse(raw_value).ok())
+    }
+
+    /// Sets `Header` into `Headers`, overriding `Header` if it
+    /// was already present in `Headers`
+    pub fn set<H: Header>(&mut self, header: H) {
+        self.insert_raw(header.display());
+    }
+
+    /// Remove `Header` from `Headers`, returning it
+    ///
+    /// Returns `None` if `Header` isn't in `Headers`.
+    pub fn remove<H: Header>(&mut self) -> Option<H> {
+        self.remove_raw(&H::name())
+            .and_then(|value| H::parse(&value.raw_value).ok())
+    }
+
+    /// Clears `Headers`, removing all headers from it
+    ///
+    /// Any pre-allocated capacity is left untouched.
+    #[inline]
+    pub fn clear(&mut self) {
+        self.headers.clear();
+    }
+
+    /// Returns a reference to the raw value of header `name`
+    ///
+    /// Returns `None` if `name` isn't present in `Headers`.
+    pub fn get_raw(&self, name: &str) -> Option<&str> {
+        self.find_header(name).map(|value| value.raw_value.as_str())
+    }
+
+    /// Inserts a raw header into `Headers`, overriding `value` if it
+    /// was already present in `Headers`.
+    pub fn insert_raw(&mut self, value: HeaderValue) {
+        match self.find_header_mut(&value.name) {
+            Some(current_value) => {
+                *current_value = value;
+            }
+            None => {
+                self.headers.push(value);
+            }
+        }
+    }
+
+    /// Remove a raw header from `Headers`, returning it
+    ///
+    /// Returns `None` if `name` isn't present in `Headers`.
+    pub fn remove_raw(&mut self, name: &str) -> Option<HeaderValue> {
+        self.find_header_index(name).map(|i| self.headers.remove(i))
+    }
+
+    pub(crate) fn find_header(&self, name: &str) -> Option<&HeaderValue> {
+        self.headers.iter().find(|value| name == value.name)
+    }
+
+    fn find_header_mut(&mut self, name: &str) -> Option<&mut HeaderValue> {
+        self.headers.iter_mut().find(|value| name == value.name)
+    }
+
+    fn find_header_index(&self, name: &str) -> Option<usize> {
+        self.headers
+            .iter()
+            .enumerate()
+            .find(|(_i, value)| name == value.name)
+            .map(|(i, _)| i)
+    }
+}
+
+impl Display for Headers {
+    /// Formats `Headers`, ready to put them into an email
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        for value in &self.headers {
+            f.write_str(&value.name)?;
+            f.write_str(": ")?;
+            f.write_str(&value.encoded_value)?;
+            f.write_str("\r\n")?;
+        }
+
+        Ok(())
+    }
+}
+
+/// A possible error when converting a `HeaderName` from another type.
+// comes from `http` crate
+#[allow(missing_copy_implementations)]
+#[derive(Debug, Clone)]
+#[non_exhaustive]
+pub struct InvalidHeaderName;
+
+impl fmt::Display for InvalidHeaderName {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        f.write_str("invalid header name")
+    }
+}
+
+impl Error for InvalidHeaderName {}
+
+/// A valid header name
+#[derive(Debug, Clone)]
+pub struct HeaderName(Cow<'static, str>);
+
+impl HeaderName {
+    /// Creates a new header name
+    pub fn new_from_ascii(ascii: String) -> Result<Self, InvalidHeaderName> {
+        if !ascii.is_empty() && ascii.len() <= 76 && ascii.is_ascii() && !ascii.contains([':', ' '])
+        {
+            Ok(Self(Cow::Owned(ascii)))
+        } else {
+            Err(InvalidHeaderName)
+        }
+    }
+
+    /// Creates a new header name, panics on invalid name
+    pub const fn new_from_ascii_str(ascii: &'static str) -> Self {
+        macro_rules! static_assert {
+            ($condition:expr) => {
+                let _ = [()][(!($condition)) as usize];
+            };
+        }
+
+        static_assert!(!ascii.is_empty());
+        static_assert!(ascii.len() <= 76);
+
+        let bytes = ascii.as_bytes();
+        let mut i = 0;
+        while i < bytes.len() {
+            static_assert!(bytes[i].is_ascii());
+            static_assert!(bytes[i] != b' ');
+            static_assert!(bytes[i] != b':');
+
+            i += 1;
+        }
+
+        Self(Cow::Borrowed(ascii))
+    }
+}
+
+impl Display for HeaderName {
+    fn fmt(&self, f: &mut Formatter<'_>) -> fmt::Result {
+        f.write_str(self)
+    }
+}
+
+impl Deref for HeaderName {
+    type Target = str;
+
+    #[inline]
+    fn deref(&self) -> &Self::Target {
+        &self.0
+    }
+}
+
+impl AsRef<[u8]> for HeaderName {
+    #[inline]
+    fn as_ref(&self) -> &[u8] {
+        let s: &str = self.as_ref();
+        s.as_bytes()
+    }
+}
+
+impl AsRef<str> for HeaderName {
+    #[inline]
+    fn as_ref(&self) -> &str {
+        &self.0
+    }
+}
+
+impl PartialEq<HeaderName> for HeaderName {
+    fn eq(&self, other: &HeaderName) -> bool {
+        self.eq_ignore_ascii_case(other)
+    }
+}
+
+impl PartialEq<&str> for HeaderName {
+    fn eq(&self, other: &&str) -> bool {
+        self.eq_ignore_ascii_case(other)
+    }
+}
+
+impl PartialEq<HeaderName> for &str {
+    fn eq(&self, other: &HeaderName) -> bool {
+        self.eq_ignore_ascii_case(other)
+    }
+}
+
+/// A safe for use header value
+#[derive(Debug, Clone, PartialEq)]
+pub struct HeaderValue {
+    name: HeaderName,
+    raw_value: String,
+    encoded_value: String,
+}
+
+impl HeaderValue {
+    /// Construct a new `HeaderValue` and encode it
+    ///
+    /// Takes the header `name` and the `raw_value` and encodes
+    /// it via `RFC2047` and line folds it.
+    ///
+    /// [`RFC2047`]: https://datatracker.ietf.org/doc/html/rfc2047
+    pub fn new(name: HeaderName, raw_value: String) -> Self {
+        let mut encoded_value = String::with_capacity(raw_value.len());
+        HeaderValueEncoder::encode(&name, &raw_value, &mut encoded_value).unwrap();
+
+        Self {
+            name,
+            raw_value,
+            encoded_value,
+        }
+    }
+
+    /// Construct a new `HeaderValue` using a pre-encoded header value
+    ///
+    /// This method is _extremely_ dangerous as it opens up
+    /// the encoder to header injection attacks, but is sometimes
+    /// acceptable for use if `encoded_value` contains only ascii
+    /// printable characters and is already line folded.
+    ///
+    /// When in doubt, use [`HeaderValue::new`].
+    pub fn dangerous_new_pre_encoded(
+        name: HeaderName,
+        raw_value: String,
+        encoded_value: String,
+    ) -> Self {
+        Self {
+            name,
+            raw_value,
+            encoded_value,
+        }
+    }
+
+    #[cfg(feature = "dkim")]
+    pub(crate) fn get_raw(&self) -> &str {
+        &self.raw_value
+    }
+
+    #[cfg(feature = "dkim")]
+    pub(crate) fn get_encoded(&self) -> &str {
+        &self.encoded_value
+    }
+}
+
+/// [RFC 1522](https://tools.ietf.org/html/rfc1522) header value encoder
+struct HeaderValueEncoder<'a> {
+    writer: EmailWriter<'a>,
+    encode_buf: String,
+}
+
+impl<'a> HeaderValueEncoder<'a> {
+    fn encode(name: &str, value: &'a str, f: &'a mut impl fmt::Write) -> fmt::Result {
+        let encoder = Self::new(name, f);
+        encoder.format(value.split_inclusive(' '))
+    }
+
+    fn new(name: &str, writer: &'a mut dyn Write) -> Self {
+        let line_len = name.len() + ": ".len();
+        let writer = EmailWriter::new(writer, line_len, 0, false);
+
+        Self {
+            writer,
+            encode_buf: String::new(),
+        }
+    }
+
+    fn format(mut self, words_iter: impl Iterator<Item = &'a str>) -> fmt::Result {
+        for next_word in words_iter {
+            let allowed = allowed_str(next_word);
+
+            if allowed {
+                // This word only contains allowed characters
+
+                // the next word is allowed, but we may have accumulated some words to encode
+                self.flush_encode_buf()?;
+
+                self.writer.folding().write_str(next_word)?;
+            } else {
+                // This word contains unallowed characters
+                self.encode_buf.push_str(next_word);
+            }
+        }
+
+        self.flush_encode_buf()?;
+
+        Ok(())
+    }
+
+    fn flush_encode_buf(&mut self) -> fmt::Result {
+        if self.encode_buf.is_empty() {
+            // nothing to encode
+            return Ok(());
+        }
+
+        let prefix = self.encode_buf.trim_end_matches(' ');
+        email_encoding::headers::rfc2047::encode(prefix, &mut self.writer)?;
+
+        // TODO: add a better API for doing this in email-encoding
+        let spaces = self.encode_buf.len() - prefix.len();
+        for _ in 0..spaces {
+            self.writer.space();
+        }
+
+        self.encode_buf.clear();
+        Ok(())
+    }
+}
+
+fn allowed_str(s: &str) -> bool {
+    s.bytes().all(allowed_char)
+}
+
+const fn allowed_char(c: u8) -> bool {
+    c >= 1 && c <= 9 || c == 11 || c == 12 || c >= 14 && c <= 127
+}
+
+#[cfg(test)]
+mod tests {
+    use pretty_assertions::assert_eq;
+
+    use super::{HeaderName, HeaderValue, Headers, To};
+    use crate::message::Mailboxes;
+
+    #[test]
+    fn valid_headername() {
+        assert!(HeaderName::new_from_ascii(String::from("From")).is_ok());
+    }
+
+    #[test]
+    fn non_ascii_headername() {
+        assert!(HeaderName::new_from_ascii(String::from("🌎")).is_err());
+    }
+
+    #[test]
+    fn spaces_in_headername() {
+        assert!(HeaderName::new_from_ascii(String::from("From ")).is_err());
+    }
+
+    #[test]
+    fn colons_in_headername() {
+        assert!(HeaderName::new_from_ascii(String::from("From:")).is_err());
+    }
+
+    #[test]
+    fn empty_headername() {
+        assert!(HeaderName::new_from_ascii("".to_owned()).is_err());
+    }
+
+    #[test]
+    fn const_valid_headername() {
+        let _ = HeaderName::new_from_ascii_str("From");
+    }
+
+    #[test]
+    #[should_panic]
+    fn const_non_ascii_headername() {
+        let _ = HeaderName::new_from_ascii_str("🌎");
+    }
+
+    #[test]
+    #[should_panic]
+    fn const_spaces_in_headername() {
+        let _ = HeaderName::new_from_ascii_str("From ");
+    }
+
+    #[test]
+    #[should_panic]
+    fn const_colons_in_headername() {
+        let _ = HeaderName::new_from_ascii_str("From:");
+    }
+
+    #[test]
+    #[should_panic]
+    fn const_empty_headername() {
+        let _ = HeaderName::new_from_ascii_str("");
+    }
+
+    #[test]
+    fn headername_headername_eq() {
+        assert_eq!(
+            HeaderName::new_from_ascii_str("From"),
+            HeaderName::new_from_ascii_str("From")
+        );
+    }
+
+    #[test]
+    fn headername_str_eq() {
+        assert_eq!(HeaderName::new_from_ascii_str("From"), "From");
+    }
+
+    #[test]
+    fn str_headername_eq() {
+        assert_eq!("From", HeaderName::new_from_ascii_str("From"));
+    }
+
+    #[test]
+    fn headername_headername_eq_case_insensitive() {
+        assert_eq!(
+            HeaderName::new_from_ascii_str("From"),
+            HeaderName::new_from_ascii_str("from")
+        );
+    }
+
+    #[test]
+    fn headername_str_eq_case_insensitive() {
+        assert_eq!(HeaderName::new_from_ascii_str("From"), "from");
+    }
+
+    #[test]
+    fn str_headername_eq_case_insensitive() {
+        assert_eq!("from", HeaderName::new_from_ascii_str("From"));
+    }
+
+    #[test]
+    fn headername_headername_ne() {
+        assert_ne!(
+            HeaderName::new_from_ascii_str("From"),
+            HeaderName::new_from_ascii_str("To")
+        );
+    }
+
+    #[test]
+    fn headername_str_ne() {
+        assert_ne!(HeaderName::new_from_ascii_str("From"), "To");
+    }
+
+    #[test]
+    fn str_headername_ne() {
+        assert_ne!("From", HeaderName::new_from_ascii_str("To"));
+    }
+
+    // names taken randomly from https://it.wikipedia.org/wiki/Pinco_Pallino
+
+    #[test]
+    fn format_ascii() {
+        let mut headers = Headers::new();
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("To"),
+            "John Doe <example@example.com>, Jean Dupont <jean@example.com>".to_owned(),
+        ));
+
+        assert_eq!(
+            headers.to_string(),
+            "To: John Doe <example@example.com>, Jean Dupont <jean@example.com>\r\n"
+        );
+    }
+
+    #[test]
+    fn format_ascii_with_folding() {
+        let mut headers = Headers::new();
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("To"),
+            "Ascii <example@example.com>, John Doe <johndoe@example.com, John Smith <johnsmith@example.com>, Pinco Pallino <pincopallino@example.com>, Jemand <jemand@example.com>, Jean Dupont <jean@example.com>".to_owned(),
+        ));
+
+        assert_eq!(
+            headers.to_string(),
+            concat!(
+                "To: Ascii <example@example.com>, John Doe <johndoe@example.com, John Smith\r\n",
+                " <johnsmith@example.com>, Pinco Pallino <pincopallino@example.com>, Jemand\r\n",
+                " <jemand@example.com>, Jean Dupont <jean@example.com>\r\n"
+            )
+        );
+    }
+
+    #[test]
+    fn format_ascii_with_folding_long_line() {
+        let mut headers = Headers::new();
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("Subject"),
+            "Hello! This is lettre, and this IsAVeryLongLineDoYouKnowWhatsGoingToHappenIGuessWeAreGoingToFindOut. Ok I guess that's it!".to_owned()
+        ));
+
+        assert_eq!(
+            headers.to_string(),
+            concat!(
+                "Subject: Hello! This is lettre, and this\r\n",
+                " IsAVeryLongLineDoYouKnowWhatsGoingToHappenIGuessWeAreGoingToFindOut. Ok I\r\n",
+                " guess that's it!\r\n"
+            )
+        );
+    }
+
+    #[test]
+    fn format_ascii_with_folding_very_long_line() {
+        let mut headers = Headers::new();
+        headers.insert_raw(
+            HeaderValue::new(
+            HeaderName::new_from_ascii_str("Subject"),
+            "Hello! IGuessTheLastLineWasntLongEnoughSoLetsTryAgainShallWeWhatDoYouThinkItsGoingToHappenIGuessWereAboutToFindOut! I don't know".to_owned()
+        ));
+
+        assert_eq!(
+            headers.to_string(),
+            concat!(
+                "Subject: Hello!\r\n",
+                " IGuessTheLastLineWasntLongEnoughSoLetsTryAgainShallWeWhatDoYouThinkItsGoingToHappenIGuessWereAboutToFindOut!\r\n",
+                " I don't know\r\n",
+            )
+        );
+    }
+
+    #[test]
+    fn format_ascii_with_folding_giant_word() {
+        let mut headers = Headers::new();
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("Subject"),
+            "1abcdefghijklmnopqrstuvwxyz2abcdefghijklmnopqrstuvwxyz3abcdefghijklmnopqrstuvwxyz4abcdefghijklmnopqrstuvwxyz5abcdefghijklmnopqrstuvwxyz6abcdefghijklmnopqrstuvwxyz".to_owned()
+        ));
+
+        assert_eq!(
+            headers.to_string(),
+            "Subject: 1abcdefghijklmnopqrstuvwxyz2abcdefghijklmnopqrstuvwxyz3abcdefghijklmnopqrstuvwxyz4abcdefghijklmnopqrstuvwxyz5abcdefghijklmnopqrstuvwxyz6abcdefghijklmnopqrstuvwxyz\r\n",
+        );
+    }
+
+    #[test]
+    fn format_special() {
+        let mut headers = Headers::new();
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("To"),
+            "Seán <sean@example.com>".to_owned(),
+        ));
+
+        assert_eq!(
+            headers.to_string(),
+            "To: =?utf-8?b?U2XDoW4=?= <sean@example.com>\r\n"
+        );
+    }
+
+    #[test]
+    fn format_special_emoji() {
+        let mut headers = Headers::new();
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("To"),
+            "🌎 <world@example.com>".to_owned(),
+        ));
+
+        assert_eq!(
+            headers.to_string(),
+            "To: =?utf-8?b?8J+Mjg==?= <world@example.com>\r\n"
+        );
+    }
+
+    #[test]
+    fn format_special_with_folding() {
+        let mut headers = Headers::new();
+        let to = To::from(Mailboxes::from_iter([
+            "🌍 <world@example.com>".parse().unwrap(),
+            "🦆 Everywhere <ducks@example.com>".parse().unwrap(),
+            "Иванов Иван Иванович <ivanov@example.com>".parse().unwrap(),
+            "Jānis Bērziņš <janis@example.com>".parse().unwrap(),
+            "Seán Ó Rudaí <sean@example.com>".parse().unwrap(),
+        ]));
+        headers.set(to);
+
+        assert_eq!(
+            headers.to_string(),
+            concat!(
+                "To: =?utf-8?b?8J+MjQ==?= <world@example.com>, =?utf-8?b?8J+mhiBFdmVyeXdo?=\r\n",
+                " =?utf-8?b?ZXJl?= <ducks@example.com>, =?utf-8?b?0JjQstCw0L3QvtCyINCY0LI=?=\r\n",
+                " =?utf-8?b?0LDQvSDQmNCy0LDQvdC+0LLQuNGH?= <ivanov@example.com>,\r\n",
+                " =?utf-8?b?SsSBbmlzIELEk3J6acWGxaE=?= <janis@example.com>, =?utf-8?b?U2U=?=\r\n",
+                " =?utf-8?b?w6FuIMOTIFJ1ZGHDrQ==?= <sean@example.com>\r\n",
+            )
+        );
+    }
+
+    #[test]
+    fn format_special_with_folding_raw() {
+        let mut headers = Headers::new();
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("To"),
+            "🌍 <world@example.com>, 🦆 Everywhere <ducks@example.com>, Иванов Иван Иванович <ivanov@example.com>, Jānis Bērziņš <janis@example.com>, Seán Ó Rudaí <sean@example.com>".to_owned(),
+        ));
+
+        assert_eq!(
+            headers.to_string(),
+            concat!(
+                "To: =?utf-8?b?8J+MjQ==?= <world@example.com>, =?utf-8?b?8J+mhg==?=\r\n",
+                " Everywhere <ducks@example.com>, =?utf-8?b?0JjQstCw0L3QvtCyINCY0LLQsNC9?=\r\n",
+                " =?utf-8?b?INCY0LLQsNC90L7QstC40Yc=?= <ivanov@example.com>,\r\n",
+                " =?utf-8?b?SsSBbmlzIELEk3J6acWGxaE=?= <janis@example.com>, =?utf-8?b?U2U=?=\r\n",
+                " =?utf-8?b?w6FuIMOTIFJ1ZGHDrQ==?= <sean@example.com>\r\n",
+            )
+        );
+    }
+
+    #[test]
+    fn format_slice_on_char_boundary_bug() {
+        let mut headers = Headers::new();
+        headers.insert_raw(
+            HeaderValue::new(
+            HeaderName::new_from_ascii_str("Subject"),
+            "🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳".to_owned(),)
+        );
+
+        assert_eq!(
+            headers.to_string(),
+            concat!(
+                "Subject: =?utf-8?b?8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz?=\r\n",
+                " =?utf-8?b?8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbM=?=\r\n",
+                " =?utf-8?b?8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbM=?=\r\n",
+                " =?utf-8?b?8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbM=?=\r\n",
+                " =?utf-8?b?8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbM=?=\r\n",
+                " =?utf-8?b?8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+lsw==?=\r\n"
+            )
+        );
+    }
+
+    #[test]
+    fn format_bad_stuff() {
+        let mut headers = Headers::new();
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("Subject"),
+            "Hello! \r\n This is \" bad \0. 👋".to_owned(),
+        ));
+
+        assert_eq!(
+            headers.to_string(),
+            "Subject: Hello! =?utf-8?b?DQo=?= This is \" bad =?utf-8?b?AC4g8J+Riw==?=\r\n"
+        );
+    }
+
+    #[test]
+    fn format_everything() {
+        let mut headers = Headers::new();
+        headers.insert_raw(
+            HeaderValue::new(
+            HeaderName::new_from_ascii_str("Subject"),
+            "Hello! This is lettre, and this IsAVeryLongLineDoYouKnowWhatsGoingToHappenIGuessWeAreGoingToFindOut. Ok I guess that's it!".to_owned()
+            )
+        );
+        headers.insert_raw(
+            HeaderValue::new(
+            HeaderName::new_from_ascii_str("To"),
+            "🌍 <world@example.com>, 🦆 Everywhere <ducks@example.com>, Иванов Иван Иванович <ivanov@example.com>, Jānis Bērziņš <janis@example.com>, Seán Ó Rudaí <sean@example.com>".to_owned(),
+            )
+        );
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("From"),
+            "Someone <somewhere@example.com>".to_owned(),
+        ));
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("Content-Transfer-Encoding"),
+            "quoted-printable".to_owned(),
+        ));
+
+        assert_eq!(
+            headers.to_string(),
+            concat!(
+                "Subject: Hello! This is lettre, and this\r\n",
+                " IsAVeryLongLineDoYouKnowWhatsGoingToHappenIGuessWeAreGoingToFindOut. Ok I\r\n",
+                " guess that's it!\r\n",
+                "To: =?utf-8?b?8J+MjQ==?= <world@example.com>, =?utf-8?b?8J+mhg==?=\r\n",
+                " Everywhere <ducks@example.com>, =?utf-8?b?0JjQstCw0L3QvtCyINCY0LLQsNC9?=\r\n",
+                " =?utf-8?b?INCY0LLQsNC90L7QstC40Yc=?= <ivanov@example.com>,\r\n",
+                " =?utf-8?b?SsSBbmlzIELEk3J6acWGxaE=?= <janis@example.com>, =?utf-8?b?U2U=?=\r\n",
+                " =?utf-8?b?w6FuIMOTIFJ1ZGHDrQ==?= <sean@example.com>\r\n",
+                "From: Someone <somewhere@example.com>\r\n",
+                "Content-Transfer-Encoding: quoted-printable\r\n",
+            )
+        );
+    }
+
+    #[test]
+    fn issue_653() {
+        let mut headers = Headers::new();
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("Subject"),
+            "＋仮名 :a;go; ;;;;;s;;;;;;;;;;;;;;;;fffeinmjgggggggggｆっ".to_owned(),
+        ));
+
+        assert_eq!(
+            headers.to_string(),
+            concat!(
+                "Subject: =?utf-8?b?77yL5Luu5ZCN?= :a;go; =?utf-8?b?Ozs7OztzOzs7Ozs7Ozs7?=\r\n",
+                " =?utf-8?b?Ozs7Ozs7O2ZmZmVpbm1qZ2dnZ2dnZ2dn772G44Gj?=\r\n",
+            )
+        );
+    }
+}

src/message/header/special.rs

@@ -1,21 +1,62 @@
-use hyperx::{
-    header::{Formatter as HeaderFormatter, Header, RawLike},
-    Error as HeaderError, Result as HyperResult,
+use crate::{
+    message::header::{Header, HeaderName, HeaderValue},
+    BoxError,
 };
-use std::{fmt::Result as FmtResult, str::from_utf8};
 
-#[derive(Debug, Clone, Copy, PartialEq)]
+/// Message format version, defined in [RFC2045](https://tools.ietf.org/html/rfc2045#section-4)
+#[derive(Debug, Copy, Clone, PartialEq, Eq)]
 pub struct MimeVersion {
-    pub major: u8,
-    pub minor: u8,
+    major: u8,
+    minor: u8,
 }
 
-pub const MIME_VERSION_1_0: MimeVersion = MimeVersion { major: 1, minor: 0 };
+/// MIME version 1.0
+///
+/// Should be used in all MIME messages.
+pub const MIME_VERSION_1_0: MimeVersion = MimeVersion::new(1, 0);
 
 impl MimeVersion {
-    pub fn new(major: u8, minor: u8) -> Self {
+    /// Build a new `MimeVersion` header
+    pub const fn new(major: u8, minor: u8) -> Self {
         MimeVersion { major, minor }
     }
+
+    /// Get the `major` value of this `MimeVersion` header.
+    #[inline]
+    pub const fn major(self) -> u8 {
+        self.major
+    }
+
+    /// Get the `minor` value of this `MimeVersion` header.
+    #[inline]
+    pub const fn minor(self) -> u8 {
+        self.minor
+    }
+}
+
+impl Header for MimeVersion {
+    fn name() -> HeaderName {
+        HeaderName::new_from_ascii_str("MIME-Version")
+    }
+
+    fn parse(s: &str) -> Result<Self, BoxError> {
+        let mut s = s.split('.');
+
+        let major = s
+            .next()
+            .expect("The first call to next for a Split<char> always succeeds");
+        let minor = s
+            .next()
+            .ok_or_else(|| String::from("MIME-Version header doesn't contain '.'"))?;
+        let major = major.parse()?;
+        let minor = minor.parse()?;
+        Ok(MimeVersion::new(major, minor))
+    }
+
+    fn display(&self) -> HeaderValue {
+        let val = format!("{}.{}", self.major, self.minor);
+        HeaderValue::dangerous_new_pre_encoded(Self::name(), val.clone(), val)
+    }
 }
 
 impl Default for MimeVersion {
@@ -24,36 +65,12 @@ impl Default for MimeVersion {
     }
 }
 
-impl Header for MimeVersion {
-    fn header_name() -> &'static str {
-        "MIME-Version"
-    }
-
-    fn parse_header<'a, T>(raw: &'a T) -> HyperResult<Self>
-    where
-        T: RawLike<'a>,
-        Self: Sized,
-    {
-        raw.one().ok_or(HeaderError::Header).and_then(|r| {
-            let mut s = from_utf8(r).map_err(|_| HeaderError::Header)?.split('.');
-
-            let major = s.next().ok_or(HeaderError::Header)?;
-            let minor = s.next().ok_or(HeaderError::Header)?;
-            let major = major.parse().map_err(|_| HeaderError::Header)?;
-            let minor = minor.parse().map_err(|_| HeaderError::Header)?;
-            Ok(MimeVersion::new(major, minor))
-        })
-    }
-
-    fn fmt_header(&self, f: &mut HeaderFormatter<'_, '_>) -> FmtResult {
-        f.fmt_line(&format!("{}.{}", self.major, self.minor))
-    }
-}
-
 #[cfg(test)]
 mod test {
+    use pretty_assertions::assert_eq;
+
     use super::{MimeVersion, MIME_VERSION_1_0};
-    use hyperx::header::Headers;
+    use crate::message::header::{HeaderName, HeaderValue, Headers};
 
     #[test]
     fn format_mime_version() {
@@ -61,23 +78,29 @@ mod test {
 
         headers.set(MIME_VERSION_1_0);
 
-        assert_eq!(format!("{}", headers), "MIME-Version: 1.0\r\n");
+        assert_eq!(headers.to_string(), "MIME-Version: 1.0\r\n");
 
         headers.set(MimeVersion::new(0, 1));
 
-        assert_eq!(format!("{}", headers), "MIME-Version: 0.1\r\n");
+        assert_eq!(headers.to_string(), "MIME-Version: 0.1\r\n");
     }
 
     #[test]
     fn parse_mime_version() {
         let mut headers = Headers::new();
 
-        headers.set_raw("MIME-Version", "1.0");
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("MIME-Version"),
+            "1.0".to_owned(),
+        ));
 
-        assert_eq!(headers.get::<MimeVersion>(), Some(&MIME_VERSION_1_0));
+        assert_eq!(headers.get::<MimeVersion>(), Some(MIME_VERSION_1_0));
 
-        headers.set_raw("MIME-Version", "0.1");
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("MIME-Version"),
+            "0.1".to_owned(),
+        ));
 
-        assert_eq!(headers.get::<MimeVersion>(), Some(&MimeVersion::new(0, 1)));
+        assert_eq!(headers.get::<MimeVersion>(), Some(MimeVersion::new(0, 1)));
     }
 }

src/message/header/textual.rs

@@ -1,70 +1,101 @@
-use crate::message::utf8_b;
-use hyperx::{
-    header::{Formatter as HeaderFormatter, Header, RawLike},
-    Error as HeaderError, Result as HyperResult,
-};
-use std::{fmt::Result as FmtResult, str::from_utf8};
+use super::{Header, HeaderName, HeaderValue};
+use crate::BoxError;
 
 macro_rules! text_header {
-    ( $type_name: ident, $header_name: expr ) => {
-        #[derive(Debug, Clone, PartialEq)]
-        pub struct $type_name(pub String);
+    ($(#[$attr:meta])* Header($type_name: ident, $header_name: expr )) => {
+        $(#[$attr])*
+        #[derive(Debug, Clone, PartialEq, Eq)]
+        pub struct $type_name(String);
 
         impl Header for $type_name {
-            fn header_name() -> &'static str {
-                $header_name
+            fn name() -> HeaderName {
+                HeaderName::new_from_ascii_str($header_name)
             }
 
-            fn parse_header<'a, T>(raw: &'a T) -> HyperResult<$type_name>
-            where
-                T: RawLike<'a>,
-                Self: Sized,
-            {
-                raw.one()
-                    .ok_or(HeaderError::Header)
-                    .and_then(parse_text)
-                    .map($type_name)
+            fn parse(s: &str) -> Result<Self, BoxError> {
+                Ok(Self(s.into()))
             }
 
-            fn fmt_header(&self, f: &mut HeaderFormatter<'_, '_>) -> FmtResult {
-                fmt_text(&self.0, f)
+            fn display(&self) -> HeaderValue {
+             HeaderValue::new(Self::name(),   self.0.clone())
+            }
+        }
+
+        impl From<String> for $type_name {
+            #[inline]
+            fn from(text: String) -> Self {
+                Self(text)
+            }
+        }
+
+        impl AsRef<str> for $type_name {
+            #[inline]
+            fn as_ref(&self) -> &str {
+                &self.0
             }
         }
     };
 }
 
-text_header!(Subject, "Subject");
-text_header!(Comments, "Comments");
-text_header!(Keywords, "Keywords");
-text_header!(InReplyTo, "In-Reply-To");
-text_header!(References, "References");
-text_header!(MessageId, "Message-Id");
-text_header!(UserAgent, "User-Agent");
-
-fn parse_text(raw: &[u8]) -> HyperResult<String> {
-    if let Ok(src) = from_utf8(raw) {
-        if let Some(txt) = utf8_b::decode(src) {
-            return Ok(txt);
-        }
-    }
-    Err(HeaderError::Header)
+text_header!(
+    /// `Subject` of the message, defined in [RFC5322](https://tools.ietf.org/html/rfc5322#section-3.6.5)
+    Header(Subject, "Subject")
+);
+text_header!(
+    /// `Comments` of the message, defined in [RFC5322](https://tools.ietf.org/html/rfc5322#section-3.6.5)
+    Header(Comments, "Comments")
+);
+text_header!(
+    /// `Keywords` header. Should contain a comma-separated list of one or more
+    /// words or quoted-strings, defined in [RFC5322](https://tools.ietf.org/html/rfc5322#section-3.6.5)
+    Header(Keywords, "Keywords")
+);
+text_header!(
+    /// `In-Reply-To` header. Contains one or more
+    /// unique message identifiers,
+    /// defined in [RFC5322](https://tools.ietf.org/html/rfc5322#section-3.6.4)
+    Header(InReplyTo, "In-Reply-To")
+);
+text_header!(
+    /// `References` header. Contains one or more
+    /// unique message identifiers,
+    /// defined in [RFC5322](https://tools.ietf.org/html/rfc5322#section-3.6.4)
+    Header(References, "References")
+);
+text_header!(
+    /// `Message-Id` header. Contains a unique message identifier,
+    /// defined in [RFC5322](https://tools.ietf.org/html/rfc5322#section-3.6.4)
+    Header(MessageId, "Message-ID")
+);
+text_header!(
+    /// `User-Agent` header. Contains information about the client,
+    /// defined in [draft-melnikov-email-user-agent-00](https://tools.ietf.org/html/draft-melnikov-email-user-agent-00#section-3)
+    Header(UserAgent, "User-Agent")
+);
+text_header! {
+    /// `Content-Id` header,
+    /// defined in [RFC2045](https://tools.ietf.org/html/rfc2045#section-7)
+    Header(ContentId, "Content-ID")
 }
-
-fn fmt_text(s: &str, f: &mut HeaderFormatter<'_, '_>) -> FmtResult {
-    f.fmt_line(&utf8_b::encode(s))
+text_header! {
+    /// `Content-Location` header,
+    /// defined in [RFC2110](https://tools.ietf.org/html/rfc2110#section-4.3)
+    Header(ContentLocation, "Content-Location")
 }
 
 #[cfg(test)]
 mod test {
+    use pretty_assertions::assert_eq;
+
     use super::Subject;
-    use hyperx::header::Headers;
+    use crate::message::header::{HeaderName, HeaderValue, Headers};
 
     #[test]
     fn format_ascii() {
         let mut headers = Headers::new();
         headers.set(Subject("Sample subject".into()));
 
-        assert_eq!(format!("{}", headers), "Subject: Sample subject\r\n");
+        assert_eq!(headers.to_string(), "Subject: Sample subject\r\n");
     }
 
     #[test]
@@ -73,33 +104,33 @@ mod test {
         headers.set(Subject("Тема сообщения".into()));
 
         assert_eq!(
-            format!("{}", headers),
+            headers.to_string(),
             "Subject: =?utf-8?b?0KLQtdC80LAg0YHQvtC+0LHRidC10L3QuNGP?=\r\n"
         );
     }
 
+    #[test]
+    fn format_utf8_word() {
+        let mut headers = Headers::new();
+        headers.set(Subject("Administratör".into()));
+
+        assert_eq!(
+            headers.to_string(),
+            "Subject: =?utf-8?b?QWRtaW5pc3RyYXTDtnI=?=\r\n"
+        );
+    }
+
     #[test]
     fn parse_ascii() {
         let mut headers = Headers::new();
-        headers.set_raw("Subject", "Sample subject");
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("Subject"),
+            "Sample subject".to_owned(),
+        ));
 
         assert_eq!(
             headers.get::<Subject>(),
-            Some(&Subject("Sample subject".into()))
-        );
-    }
-
-    #[test]
-    fn parse_utf8() {
-        let mut headers = Headers::new();
-        headers.set_raw(
-            "Subject",
-            "=?utf-8?b?0KLQtdC80LAg0YHQvtC+0LHRidC10L3QuNGP?=",
-        );
-
-        assert_eq!(
-            headers.get::<Subject>(),
-            Some(&Subject("Тема сообщения".into()))
+            Some(Subject("Sample subject".into()))
         );
     }
 }

src/message/mailbox/mod.rs

@@ -1,3 +1,4 @@
+mod parsers;
 #[cfg(feature = "serde")]
 mod serde;
 mod types;

src/message/mailbox/parsers/mod.rs

@@ -0,0 +1,5 @@
+mod rfc2234;
+mod rfc2822;
+mod rfc5336;
+
+pub(crate) use rfc2822::{mailbox, mailbox_list};

src/message/mailbox/parsers/rfc2234.rs

@@ -0,0 +1,32 @@
+//! Partial parsers implementation of [RFC2234]: Augmented BNF for
+//! Syntax Specifications: ABNF.
+//!
+//! [RFC2234]: https://datatracker.ietf.org/doc/html/rfc2234
+
+use chumsky::{error::Cheap, prelude::*};
+
+// 6.1  Core Rules
+// https://datatracker.ietf.org/doc/html/rfc2234#section-6.1
+
+// ALPHA          =  %x41-5A / %x61-7A   ; A-Z / a-z
+pub(super) fn alpha() -> impl Parser<char, char, Error = Cheap<char>> {
+    filter(|c: &char| c.is_ascii_alphabetic())
+}
+
+// DIGIT          =  %x30-39
+//                        ; 0-9
+pub(super) fn digit() -> impl Parser<char, char, Error = Cheap<char>> {
+    filter(|c: &char| c.is_ascii_digit())
+}
+
+// DQUOTE         =  %x22
+//                        ; " (Double Quote)
+pub(super) fn dquote() -> impl Parser<char, char, Error = Cheap<char>> {
+    just('"')
+}
+
+// WSP            =  SP / HTAB
+//                        ; white space
+pub(super) fn wsp() -> impl Parser<char, char, Error = Cheap<char>> {
+    choice((just(' '), just('\t')))
+}

src/message/mailbox/parsers/rfc2822.rs

@@ -0,0 +1,250 @@
+//! Partial parsers implementation of [RFC2822]: Internet Message
+//! Format.
+//!
+//! [RFC2822]: https://datatracker.ietf.org/doc/html/rfc2822
+
+use chumsky::{error::Cheap, prelude::*};
+
+use super::{rfc2234, rfc5336};
+
+// 3.2.1. Primitive Tokens
+// https://datatracker.ietf.org/doc/html/rfc2822#section-3.2.1
+
+// NO-WS-CTL       =       %d1-8 /         ; US-ASCII control characters
+//                         %d11 /          ;  that do not include the
+//                         %d12 /          ;  carriage return, line feed,
+//                         %d14-31 /       ;  and white space characters
+//                         %d127
+fn no_ws_ctl() -> impl Parser<char, char, Error = Cheap<char>> {
+    filter(|c| matches!(u32::from(*c), 1..=8 | 11 | 12 | 14..=31 | 127))
+}
+
+// text            =       %d1-9 /         ; Characters excluding CR and LF
+//                         %d11 /
+//                         %d12 /
+//                         %d14-127 /
+//                         obs-text
+fn text() -> impl Parser<char, char, Error = Cheap<char>> {
+    filter(|c| matches!(u32::from(*c), 1..=9 | 11 | 12 | 14..=127))
+}
+
+// 3.2.2. Quoted characters
+// https://datatracker.ietf.org/doc/html/rfc2822#section-3.2.2
+
+// quoted-pair     =       ("\" text) / obs-qp
+fn quoted_pair() -> impl Parser<char, char, Error = Cheap<char>> {
+    just('\\').ignore_then(text())
+}
+
+// 3.2.3. Folding white space and comments
+// https://datatracker.ietf.org/doc/html/rfc2822#section-3.2.3
+
+// FWS             =       ([*WSP CRLF] 1*WSP) /   ; Folding white space
+//                         obs-FWS
+pub(super) fn fws() -> impl Parser<char, Option<char>, Error = Cheap<char>> {
+    rfc2234::wsp()
+        .or_not()
+        .then_ignore(rfc2234::wsp().ignored().repeated())
+}
+
+// CFWS            =       *([FWS] comment) (([FWS] comment) / FWS)
+pub(super) fn cfws() -> impl Parser<char, Option<char>, Error = Cheap<char>> {
+    // TODO: comment are not currently supported, so for now a cfws is
+    // the same as a fws.
+    fws()
+}
+
+// 3.2.4. Atom
+// https://datatracker.ietf.org/doc/html/rfc2822#section-3.2.4
+
+// atext           =       ALPHA / DIGIT / ; Any character except controls,
+//                         "!" / "#" /     ;  SP, and specials.
+//                         "$" / "%" /     ;  Used for atoms
+//                         "&" / "'" /
+//                         "*" / "+" /
+//                         "-" / "/" /
+//                         "=" / "?" /
+//                         "^" / "_" /
+//                         "`" / "{" /
+//                         "|" / "}" /
+//                         "~"
+pub(super) fn atext() -> impl Parser<char, char, Error = Cheap<char>> {
+    choice((
+        rfc2234::alpha(),
+        rfc2234::digit(),
+        filter(|c| {
+            matches!(
+                *c,
+                '!' | '#'
+                    | '$'
+                    | '%'
+                    | '&'
+                    | '\''
+                    | '*'
+                    | '+'
+                    | '-'
+                    | '/'
+                    | '='
+                    | '?'
+                    | '^'
+                    | '_'
+                    | '`'
+                    | '{'
+                    | '|'
+                    | '}'
+                    | '~'
+            )
+        }),
+        // also allow non ASCII UTF8 chars
+        rfc5336::utf8_non_ascii(),
+    ))
+}
+
+// atom            =       [CFWS] 1*atext [CFWS]
+pub(super) fn atom() -> impl Parser<char, Vec<char>, Error = Cheap<char>> {
+    cfws().chain(atext().repeated().at_least(1))
+}
+
+// dot-atom        =       [CFWS] dot-atom-text [CFWS]
+pub(super) fn dot_atom() -> impl Parser<char, Vec<char>, Error = Cheap<char>> {
+    cfws().chain(dot_atom_text())
+}
+
+// dot-atom-text   =       1*atext *("." 1*atext)
+pub(super) fn dot_atom_text() -> impl Parser<char, Vec<char>, Error = Cheap<char>> {
+    atext().repeated().at_least(1).chain(
+        just('.')
+            .chain(atext().repeated().at_least(1))
+            .repeated()
+            .at_least(1)
+            .flatten(),
+    )
+}
+
+// 3.2.5. Quoted strings
+// https://datatracker.ietf.org/doc/html/rfc2822#section-3.2.5
+
+// qtext           =       NO-WS-CTL /     ; Non white space controls
+//
+//                         %d33 /          ; The rest of the US-ASCII
+//                         %d35-91 /       ;  characters not including "\"
+//                         %d93-126        ;  or the quote character
+fn qtext() -> impl Parser<char, char, Error = Cheap<char>> {
+    choice((
+        filter(|c| matches!(u32::from(*c), 33 | 35..=91 | 93..=126)),
+        no_ws_ctl(),
+    ))
+}
+
+// qcontent        =       qtext / quoted-pair
+pub(super) fn qcontent() -> impl Parser<char, char, Error = Cheap<char>> {
+    choice((qtext(), quoted_pair(), rfc5336::utf8_non_ascii()))
+}
+
+// quoted-string   =       [CFWS]
+//                         DQUOTE *([FWS] qcontent) [FWS] DQUOTE
+//                         [CFWS]
+fn quoted_string() -> impl Parser<char, Vec<char>, Error = Cheap<char>> {
+    rfc2234::dquote()
+        .ignore_then(fws().chain(qcontent()).repeated().flatten())
+        .then_ignore(text::whitespace())
+        .then_ignore(rfc2234::dquote())
+}
+
+// 3.2.6. Miscellaneous tokens
+// https://datatracker.ietf.org/doc/html/rfc2822#section-3.2.6
+
+// word            =       atom / quoted-string
+fn word() -> impl Parser<char, Vec<char>, Error = Cheap<char>> {
+    choice((quoted_string(), atom()))
+}
+
+// phrase          =       1*word / obs-phrase
+fn phrase() -> impl Parser<char, Vec<char>, Error = Cheap<char>> {
+    choice((obs_phrase(), word().repeated().at_least(1).flatten()))
+}
+
+// 3.4. Address Specification
+// https://datatracker.ietf.org/doc/html/rfc2822#section-3.4
+
+// mailbox         =       name-addr / addr-spec
+pub(crate) fn mailbox() -> impl Parser<char, (Option<String>, (String, String)), Error = Cheap<char>>
+{
+    choice((name_addr(), addr_spec().map(|addr| (None, addr))))
+        .padded()
+        .then_ignore(end())
+}
+
+// name-addr       =       [display-name] angle-addr
+fn name_addr() -> impl Parser<char, (Option<String>, (String, String)), Error = Cheap<char>> {
+    display_name().collect().or_not().then(angle_addr())
+}
+
+// angle-addr      =       [CFWS] "<" addr-spec ">" [CFWS] / obs-angle-addr
+fn angle_addr() -> impl Parser<char, (String, String), Error = Cheap<char>> {
+    addr_spec()
+        .delimited_by(just('<').ignored(), just('>').ignored())
+        .padded()
+}
+
+// display-name    =       phrase
+fn display_name() -> impl Parser<char, Vec<char>, Error = Cheap<char>> {
+    phrase()
+}
+
+// mailbox-list    =       (mailbox *("," mailbox)) / obs-mbox-list
+pub(crate) fn mailbox_list(
+) -> impl Parser<char, Vec<(Option<String>, (String, String))>, Error = Cheap<char>> {
+    choice((name_addr(), addr_spec().map(|addr| (None, addr))))
+        .separated_by(just(',').padded())
+        .then_ignore(end())
+}
+
+// 3.4.1. Addr-spec specification
+// https://datatracker.ietf.org/doc/html/rfc2822#section-3.4.1
+
+// addr-spec       =       local-part "@" domain
+pub(super) fn addr_spec() -> impl Parser<char, (String, String), Error = Cheap<char>> {
+    local_part()
+        .collect()
+        .then_ignore(just('@'))
+        .then(domain().collect())
+}
+
+// local-part      =       dot-atom / quoted-string / obs-local-part
+pub(super) fn local_part() -> impl Parser<char, Vec<char>, Error = Cheap<char>> {
+    choice((dot_atom(), quoted_string(), obs_local_part()))
+}
+
+// domain          =       dot-atom / domain-literal / obs-domain
+pub(super) fn domain() -> impl Parser<char, Vec<char>, Error = Cheap<char>> {
+    // NOTE: omitting domain-literal since it may never be used
+    choice((dot_atom(), obs_domain()))
+}
+
+// 4.1. Miscellaneous obsolete tokens
+// https://datatracker.ietf.org/doc/html/rfc2822#section-4.1
+
+// obs-phrase      =       word *(word / "." / CFWS)
+fn obs_phrase() -> impl Parser<char, Vec<char>, Error = Cheap<char>> {
+    // NOTE: the CFWS is already captured by the word, no need to add
+    // it there.
+    word().chain(
+        choice((word(), just('.').repeated().exactly(1)))
+            .repeated()
+            .flatten(),
+    )
+}
+
+// 4.4. Obsolete Addressing
+// https://datatracker.ietf.org/doc/html/rfc2822#section-4.4
+
+// obs-local-part  =       word *("." word)
+pub(super) fn obs_local_part() -> impl Parser<char, Vec<char>, Error = Cheap<char>> {
+    word().chain(just('.').chain(word()).repeated().flatten())
+}
+
+// obs-domain      =       atom *("." atom)
+pub(super) fn obs_domain() -> impl Parser<char, Vec<char>, Error = Cheap<char>> {
+    atom().chain(just('.').chain(atom()).repeated().flatten())
+}

src/message/mailbox/parsers/rfc5336.rs

@@ -0,0 +1,17 @@
+//! Partial parsers implementation of [RFC5336]: SMTP Extension for
+//! Internationalized Email Addresses.
+//!
+//! [RFC5336]: https://datatracker.ietf.org/doc/html/rfc5336
+
+use chumsky::{error::Cheap, prelude::*};
+
+// 3.3.  Extended Mailbox Address Syntax
+// https://datatracker.ietf.org/doc/html/rfc5336#section-3.3
+
+// UTF8-non-ascii = UTF8-2 / UTF8-3 / UTF8-4
+// UTF8-2 =  <See Section 4 of RFC 3629>
+// UTF8-3 =  <See Section 4 of RFC 3629>
+// UTF8-4 =  <See Section 4 of RFC 3629>
+pub(super) fn utf8_non_ascii() -> impl Parser<char, char, Error = Cheap<char>> {
+    filter(|c: &char| c.len_utf8() > 1)
+}

src/message/mailbox/serde.rs

@@ -1,17 +1,19 @@
-use crate::message::{Mailbox, Mailboxes};
+use std::fmt::{Formatter, Result as FmtResult};
+
 use serde::{
     de::{Deserializer, Error as DeError, MapAccess, SeqAccess, Visitor},
     ser::Serializer,
     Deserialize, Serialize,
 };
-use std::fmt::{Formatter, Result as FmtResult};
+
+use crate::message::{Mailbox, Mailboxes};
 
 impl Serialize for Mailbox {
     fn serialize<S>(&self, serializer: S) -> Result<S::Ok, S::Error>
     where
         S: Serializer,
     {
-        serializer.serialize_str(&self.to_string())
+        serializer.collect_str(self)
     }
 }
 
@@ -34,7 +36,7 @@ impl<'de> Deserialize<'de> for Mailbox {
             {
                 struct FieldVisitor;
 
-                impl<'de> Visitor<'de> for FieldVisitor {
+                impl Visitor<'_> for FieldVisitor {
                     type Value = Field;
 
                     fn expecting(&self, formatter: &mut Formatter<'_>) -> FmtResult {
@@ -109,7 +111,7 @@ impl Serialize for Mailboxes {
     where
         S: Serializer,
     {
-        serializer.serialize_str(&self.to_string())
+        serializer.collect_str(self)
     }
 }
 
@@ -152,9 +154,11 @@ impl<'de> Deserialize<'de> for Mailboxes {
 
 #[cfg(test)]
 mod test {
+    use pretty_assertions::assert_eq;
+    use serde_json::from_str;
+
     use super::*;
     use crate::address::Address;
-    use serde_json::from_str;
 
     #[test]
     fn parse_address_string() {
@@ -175,7 +179,7 @@ mod test {
     }
 
     #[test]
-    fn parse_mailbox_object_address_stirng() {
+    fn parse_mailbox_object_address_string() {
         let m: Mailbox = from_str(r#"{ "name": "Kai", "email": "kayo@example.com" }"#).unwrap();
         assert_eq!(m, "Kai <kayo@example.com>".parse().unwrap());
     }
@@ -194,7 +198,7 @@ mod test {
             from_str(r#""yin@dtb.com, Hei <hei@dtb.com>, Kai <kayo@example.com>""#).unwrap();
         assert_eq!(
             m,
-            "<yin@dtb.com>, Hei <hei@dtb.com>, Kai <kayo@example.com>"
+            "yin@dtb.com, Hei <hei@dtb.com>, Kai <kayo@example.com>"
                 .parse()
                 .unwrap()
         );
@@ -207,7 +211,7 @@ mod test {
                 .unwrap();
         assert_eq!(
             m,
-            "<yin@dtb.com>, Hei <hei@dtb.com>, Kai <kayo@example.com>"
+            "yin@dtb.com, Hei <hei@dtb.com>, Kai <kayo@example.com>"
                 .parse()
                 .unwrap()
         );

src/message/mailbox/types.rs

@@ -1,19 +1,21 @@
-use crate::{
-    address::{Address, AddressError},
-    message::utf8_b,
-};
 use std::{
-    convert::TryFrom,
     fmt::{Display, Formatter, Result as FmtResult, Write},
+    mem,
     slice::Iter,
     str::FromStr,
 };
 
+use chumsky::prelude::*;
+use email_encoding::headers::writer::EmailWriter;
+
+use super::parsers;
+use crate::address::{Address, AddressError};
+
 /// Represents an email address with an optional name for the sender/recipient.
 ///
 /// This type contains email address and the sender/recipient name (_Some Name \<user@domain.tld\>_ or _withoutname@domain.tld_).
 ///
-/// **NOTE**: Enable feature "serde" to be able serialize/deserialize it using [serde](https://serde.rs/).
+/// **NOTE**: Enable feature "serde" to be able to serialize/deserialize it using [serde](https://serde.rs/).
 ///
 /// # Examples
 ///
@@ -54,7 +56,7 @@ impl Mailbox {
     /// # Examples
     ///
     /// ```
-    /// use lettre::{Address, message::Mailbox};
+    /// use lettre::{message::Mailbox, Address};
     ///
     /// # use std::error::Error;
     /// # fn main() -> Result<(), Box<dyn Error>> {
@@ -67,21 +69,29 @@ impl Mailbox {
         Mailbox { name, email }
     }
 
-    /// Encode addressee name using function
-    pub(crate) fn recode_name<F>(&self, f: F) -> Self
-    where
-        F: FnOnce(&str) -> String,
-    {
-        Mailbox::new(self.name.clone().map(|s| f(&s)), self.email.clone())
+    pub(crate) fn encode(&self, w: &mut EmailWriter<'_>) -> FmtResult {
+        if let Some(name) = &self.name {
+            email_encoding::headers::quoted_string::encode(name, w)?;
+            w.space();
+            w.write_char('<')?;
+        }
+
+        w.write_str(self.email.as_ref())?;
+
+        if self.name.is_some() {
+            w.write_char('>')?;
+        }
+
+        Ok(())
     }
 }
 
 impl Display for Mailbox {
     fn fmt(&self, f: &mut Formatter<'_>) -> FmtResult {
-        if let Some(ref name) = self.name {
+        if let Some(name) = &self.name {
             let name = name.trim();
             if !name.is_empty() {
-                f.write_str(&name)?;
+                write_word(f, name)?;
                 f.write_str(" <")?;
                 self.email.fmt(f)?;
                 return f.write_char('>');
@@ -100,40 +110,24 @@ impl<S: Into<String>, T: Into<String>> TryFrom<(S, T)> for Mailbox {
     }
 }
 
-/*
-impl<S: AsRef<&str>, T: AsRef<&str>> TryFrom<(S, T)> for Mailbox {
-    type Error = AddressError;
-
-    fn try_from(header: (S, T)) -> Result<Self, Self::Error> {
-        let (name, address) = header;
-        Ok(Mailbox::new(Some(name.as_ref()), address.as_ref().parse()?))
-    }
-}*/
-
 impl FromStr for Mailbox {
     type Err = AddressError;
 
     fn from_str(src: &str) -> Result<Mailbox, Self::Err> {
-        match (src.find('<'), src.find('>')) {
-            (Some(addr_open), Some(addr_close)) if addr_open < addr_close => {
-                let name = src.split_at(addr_open).0;
-                let addr_open = addr_open + 1;
-                let addr = src.split_at(addr_open).1.split_at(addr_close - addr_open).0;
-                let addr = addr.parse()?;
-                let name = name.trim();
-                let name = if name.is_empty() {
-                    None
-                } else {
-                    Some(name.into())
-                };
-                Ok(Mailbox::new(name, addr))
-            }
-            (Some(_), _) => Err(AddressError::Unbalanced),
-            _ => {
-                let addr = src.parse()?;
-                Ok(Mailbox::new(None, addr))
-            }
-        }
+        let (name, (user, domain)) = parsers::mailbox().parse(src).map_err(|_errs| {
+            // TODO: improve error management
+            AddressError::InvalidInput
+        })?;
+
+        let mailbox = Mailbox::new(name, Address::new(user, domain)?);
+
+        Ok(mailbox)
+    }
+}
+
+impl From<Address> for Mailbox {
+    fn from(value: Address) -> Self {
+        Self::new(None, value)
     }
 }
 
@@ -141,7 +135,7 @@ impl FromStr for Mailbox {
 ///
 /// This type contains a sequence of mailboxes (_Some Name \<user@domain.tld\>, Another Name \<other@domain.tld\>, withoutname@domain.tld, ..._).
 ///
-/// **NOTE**: Enable feature "serde" to be able serialize/deserialize it using [serde](https://serde.rs/).
+/// **NOTE**: Enable feature "serde" to be able to serialize/deserialize it using [serde](https://serde.rs/).
 #[derive(Debug, Clone, PartialOrd, Ord, PartialEq, Eq, Hash)]
 pub struct Mailboxes(Vec<Mailbox>);
 
@@ -163,7 +157,10 @@ impl Mailboxes {
     /// # Examples
     ///
     /// ```
-    /// use lettre::{Address, message::{Mailbox, Mailboxes}};
+    /// use lettre::{
+    ///     message::{Mailbox, Mailboxes},
+    ///     Address,
+    /// };
     ///
     /// # use std::error::Error;
     /// # fn main() -> Result<(), Box<dyn Error>> {
@@ -177,12 +174,15 @@ impl Mailboxes {
         self
     }
 
-    /// Adds a new [`Mailbox`] to the list, in a Vec::push style pattern.
+    /// Adds a new [`Mailbox`] to the list, in a `Vec::push` style pattern.
     ///
     /// # Examples
     ///
     /// ```
-    /// use lettre::{Address, message::{Mailbox, Mailboxes}};
+    /// use lettre::{
+    ///     message::{Mailbox, Mailboxes},
+    ///     Address,
+    /// };
     ///
     /// # use std::error::Error;
     /// # fn main() -> Result<(), Box<dyn Error>> {
@@ -201,7 +201,10 @@ impl Mailboxes {
     /// # Examples
     ///
     /// ```
-    /// use lettre::{Address, message::{Mailbox, Mailboxes}};
+    /// use lettre::{
+    ///     message::{Mailbox, Mailboxes},
+    ///     Address,
+    /// };
     ///
     /// # use std::error::Error;
     /// # fn main() -> Result<(), Box<dyn Error>> {
@@ -225,7 +228,10 @@ impl Mailboxes {
     /// # Examples
     ///
     /// ```
-    /// use lettre::{Address, message::{Mailbox, Mailboxes}};
+    /// use lettre::{
+    ///     message::{Mailbox, Mailboxes},
+    ///     Address,
+    /// };
     ///
     /// # use std::error::Error;
     /// # fn main() -> Result<(), Box<dyn Error>> {
@@ -249,6 +255,20 @@ impl Mailboxes {
     pub fn iter(&self) -> Iter<'_, Mailbox> {
         self.0.iter()
     }
+
+    pub(crate) fn encode(&self, w: &mut EmailWriter<'_>) -> FmtResult {
+        let mut first = true;
+        for mailbox in self.iter() {
+            if !mem::take(&mut first) {
+                w.write_char(',')?;
+                w.space();
+            }
+
+            mailbox.encode(w)?;
+        }
+
+        Ok(())
+    }
 }
 
 impl Default for Mailboxes {
@@ -281,6 +301,18 @@ impl From<Mailboxes> for Vec<Mailbox> {
     }
 }
 
+impl FromIterator<Mailbox> for Mailboxes {
+    fn from_iter<T: IntoIterator<Item = Mailbox>>(iter: T) -> Self {
+        Self(Vec::from_iter(iter))
+    }
+}
+
+impl Extend<Mailbox> for Mailboxes {
+    fn extend<T: IntoIterator<Item = Mailbox>>(&mut self, iter: T) {
+        self.0.extend(iter);
+    }
+}
+
 impl IntoIterator for Mailboxes {
     type Item = Mailbox;
     type IntoIter = ::std::vec::IntoIter<Mailbox>;
@@ -290,14 +322,6 @@ impl IntoIterator for Mailboxes {
     }
 }
 
-impl Extend<Mailbox> for Mailboxes {
-    fn extend<T: IntoIterator<Item = Mailbox>>(&mut self, iter: T) {
-        for elem in iter {
-            self.0.push(elem);
-        }
-    }
-}
-
 impl Display for Mailboxes {
     fn fmt(&self, f: &mut Formatter<'_>) -> FmtResult {
         let mut iter = self.iter();
@@ -319,29 +343,110 @@ impl FromStr for Mailboxes {
     type Err = AddressError;
 
     fn from_str(src: &str) -> Result<Self, Self::Err> {
-        src.split(',')
-            .map(|m| {
-                m.trim().parse().and_then(|Mailbox { name, email }| {
-                    if let Some(name) = name {
-                        if let Some(name) = utf8_b::decode(&name) {
-                            Ok(Mailbox::new(Some(name), email))
-                        } else {
-                            Err(AddressError::InvalidUtf8b)
-                        }
-                    } else {
-                        Ok(Mailbox::new(None, email))
-                    }
-                })
-            })
-            .collect::<Result<Vec<_>, _>>()
-            .map(Mailboxes)
+        let mut mailboxes = Vec::new();
+
+        let parsed_mailboxes = parsers::mailbox_list().parse(src).map_err(|_errs| {
+            // TODO: improve error management
+            AddressError::InvalidInput
+        })?;
+
+        for (name, (user, domain)) in parsed_mailboxes {
+            mailboxes.push(Mailbox::new(name, Address::new(user, domain)?));
+        }
+
+        Ok(Mailboxes(mailboxes))
+    }
+}
+
+// https://datatracker.ietf.org/doc/html/rfc2822#section-3.2.6
+fn write_word(f: &mut Formatter<'_>, s: &str) -> FmtResult {
+    if s.as_bytes().iter().copied().all(is_valid_atom_char) {
+        f.write_str(s)
+    } else {
+        // Quoted string: https://datatracker.ietf.org/doc/html/rfc2822#section-3.2.5
+        f.write_char('"')?;
+        for c in s.chars() {
+            write_quoted_string_char(f, c)?;
+        }
+        f.write_char('"')?;
+
+        Ok(())
+    }
+}
+
+// https://datatracker.ietf.org/doc/html/rfc2822#section-3.2.4
+fn is_valid_atom_char(c: u8) -> bool {
+    matches!(c,
+		// Not really allowed but can be inserted between atoms.
+		b'\t' |
+		b' ' |
+
+		b'!' |
+		b'#' |
+		b'$' |
+		b'%' |
+		b'&' |
+		b'\'' |
+		b'*' |
+		b'+' |
+		b'-' |
+		b'/' |
+		b'0'..=b'8' |
+		b'=' |
+		b'?' |
+		b'A'..=b'Z' |
+		b'^' |
+		b'_' |
+		b'`' |
+		b'a'..=b'z' |
+		b'{' |
+		b'|' |
+		b'}' |
+		b'~' |
+
+		// Not technically allowed but will be escaped into allowed characters.
+		128..=255)
+}
+
+// https://datatracker.ietf.org/doc/html/rfc2822#section-3.2.5
+fn write_quoted_string_char(f: &mut Formatter<'_>, c: char) -> FmtResult {
+    match c {
+        // Can not be encoded.
+        '\n' | '\r' => Err(std::fmt::Error),
+
+        // Note, not qcontent but can be put before or after any qcontent.
+        '\t' | ' ' => f.write_char(c),
+
+        c if match c as u32 {
+            // NO-WS-CTL: https://datatracker.ietf.org/doc/html/rfc2822#section-3.2.1
+            1..=8 | 11 | 12 | 14..=31 | 127 |
+
+            // The rest of the US-ASCII except \ and "
+            33 |
+            35..=91 |
+            93..=126 |
+
+            // Non-ascii characters will be escaped separately later.
+            128.. => true,
+            _ => false,
+        } =>
+        {
+            f.write_char(c)
+        }
+
+        _ => {
+            // quoted-pair https://datatracker.ietf.org/doc/html/rfc2822#section-3.2.2
+            f.write_char('\\')?;
+            f.write_char(c)
+        }
     }
 }
 
 #[cfg(test)]
 mod test {
+    use pretty_assertions::assert_eq;
+
     use super::Mailbox;
-    use std::convert::TryInto;
 
     #[test]
     fn mailbox_format_address_only() {
@@ -361,7 +466,63 @@ mod test {
                 "{}",
                 Mailbox::new(Some("K.".into()), "kayo@example.com".parse().unwrap())
             ),
-            "K. <kayo@example.com>"
+            "\"K.\" <kayo@example.com>"
+        );
+    }
+
+    #[test]
+    fn mailbox_format_address_with_comma() {
+        assert_eq!(
+            format!(
+                "{}",
+                Mailbox::new(
+                    Some("Last, First".into()),
+                    "kayo@example.com".parse().unwrap()
+                )
+            ),
+            r#""Last, First" <kayo@example.com>"#
+        );
+    }
+
+    #[test]
+    fn mailbox_format_address_with_comma_and_non_ascii() {
+        assert_eq!(
+            format!(
+                "{}",
+                Mailbox::new(
+                    Some("Laşt, First".into()),
+                    "kayo@example.com".parse().unwrap()
+                )
+            ),
+            r#""Laşt, First" <kayo@example.com>"#
+        );
+    }
+
+    #[test]
+    fn mailbox_format_address_with_comma_and_quoted_non_ascii() {
+        assert_eq!(
+            format!(
+                "{}",
+                Mailbox::new(
+                    Some(r#"Laşt, "First""#.into()),
+                    "kayo@example.com".parse().unwrap()
+                )
+            ),
+            r#""Laşt, \"First\"" <kayo@example.com>"#
+        );
+    }
+
+    #[test]
+    fn mailbox_format_address_with_color() {
+        assert_eq!(
+            format!(
+                "{}",
+                Mailbox::new(
+                    Some("Chris's Wiki :: blog".into()),
+                    "kayo@example.com".parse().unwrap()
+                )
+            ),
+            r#""Chris's Wiki :: blog" <kayo@example.com>"#
         );
     }
 
@@ -370,7 +531,7 @@ mod test {
         assert_eq!(
             format!(
                 "{}",
-                Mailbox::new(Some("".into()), "kayo@example.com".parse().unwrap())
+                Mailbox::new(Some("".to_owned()), "kayo@example.com".parse().unwrap())
             ),
             "kayo@example.com"
         );
@@ -383,7 +544,7 @@ mod test {
                 "{}",
                 Mailbox::new(Some(" K. ".into()), "kayo@example.com".parse().unwrap())
             ),
-            "K. <kayo@example.com>"
+            "\"K.\" <kayo@example.com>"
         );
     }
 
@@ -395,6 +556,14 @@ mod test {
         );
     }
 
+    #[test]
+    fn parse_address_only_trim() {
+        assert_eq!(
+            " kayo@example.com ".parse(),
+            Ok(Mailbox::new(None, "kayo@example.com".parse().unwrap()))
+        );
+    }
+
     #[test]
     fn parse_address_with_name() {
         assert_eq!(
@@ -406,6 +575,17 @@ mod test {
         );
     }
 
+    #[test]
+    fn parse_address_with_name_trim() {
+        assert_eq!(
+            " K. <kayo@example.com> ".parse(),
+            Ok(Mailbox::new(
+                Some("K.".into()),
+                "kayo@example.com".parse().unwrap()
+            ))
+        );
+    }
+
     #[test]
     fn parse_address_with_empty_name() {
         assert_eq!(
@@ -417,7 +597,7 @@ mod test {
     #[test]
     fn parse_address_with_empty_name_trim() {
         assert_eq!(
-            " <kayo@example.com>".parse(),
+            " <kayo@example.com> ".parse(),
             Ok(Mailbox::new(None, "kayo@example.com".parse().unwrap()))
         );
     }
@@ -425,7 +605,7 @@ mod test {
     #[test]
     fn parse_address_from_tuple() {
         assert_eq!(
-            ("K.".to_string(), "kayo@example.com".to_string()).try_into(),
+            ("K.".to_owned(), "kayo@example.com".to_owned()).try_into(),
             Ok(Mailbox::new(
                 Some("K.".into()),
                 "kayo@example.com".parse().unwrap()

src/message/mimebody.rs

@@ -1,23 +1,32 @@
+use std::{io::Write, iter::repeat_with};
+
+use mime::Mime;
+
 use crate::message::{
-    header::{ContentTransferEncoding, ContentType, Header, Headers},
+    header::{self, ContentTransferEncoding, ContentType, Header, Headers},
     EmailFormat, IntoBody,
 };
-use mime::Mime;
-use rand::Rng;
 
 /// MIME part variants
-///
 #[derive(Debug, Clone)]
-pub enum Part {
+pub(super) enum Part {
     /// Single part with content
-    ///
     Single(SinglePart),
 
     /// Multiple parts of content
-    ///
     Multi(MultiPart),
 }
 
+impl Part {
+    #[cfg(feature = "dkim")]
+    pub(super) fn format_body(&self, out: &mut Vec<u8>) {
+        match self {
+            Part::Single(part) => part.format_body(out),
+            Part::Multi(part) => part.format_body(out),
+        }
+    }
+}
+
 impl EmailFormat for Part {
     fn format(&self, out: &mut Vec<u8>) {
         match self {
@@ -27,21 +36,7 @@ impl EmailFormat for Part {
     }
 }
 
-impl Part {
-    /// Get message content formatted for SMTP
-    pub fn formatted(&self) -> Vec<u8> {
-        let mut out = Vec::new();
-        self.format(&mut out);
-        out
-    }
-}
-
-/// Parts of multipart body
-///
-pub type Parts = Vec<Part>;
-
 /// Creates builder for single part
-///
 #[derive(Debug, Clone)]
 pub struct SinglePartBuilder {
     headers: Headers,
@@ -69,7 +64,7 @@ impl SinglePartBuilder {
 
     /// Build singlepart using body
     pub fn body<T: IntoBody>(mut self, body: T) -> SinglePart {
-        let maybe_encoding = self.headers.get::<ContentTransferEncoding>().copied();
+        let maybe_encoding = self.headers.get::<ContentTransferEncoding>();
         let body = body.into_body(maybe_encoding);
 
         self.headers.set(body.encoding());
@@ -92,17 +87,16 @@ impl Default for SinglePartBuilder {
 /// # Example
 ///
 /// ```
-/// use lettre::message::{SinglePart, header};
+/// use lettre::message::{header, SinglePart};
 ///
 /// # use std::error::Error;
 /// # fn main() -> Result<(), Box<dyn Error>> {
 /// let part = SinglePart::builder()
-///      .header(header::ContentType("text/plain; charset=utf8".parse()?))
-///      .body(String::from("Текст письма в уникоде"));
+///     .header(header::ContentType::TEXT_PLAIN)
+///     .body(String::from("Текст письма в уникоде"));
 /// # Ok(())
 /// # }
 /// ```
-///
 #[derive(Debug, Clone)]
 pub struct SinglePart {
     headers: Headers,
@@ -116,28 +110,18 @@ impl SinglePart {
         SinglePartBuilder::new()
     }
 
-    #[doc(hidden)]
-    #[deprecated = "Replaced by SinglePart::builder(), which chooses the best Content-Transfer-Encoding based on the provided body"]
-    pub fn seven_bit() -> SinglePartBuilder {
-        Self::builder().header(ContentTransferEncoding::SevenBit)
+    /// Directly create a `SinglePart` from a plain UTF-8 content
+    pub fn plain<T: IntoBody>(body: T) -> Self {
+        Self::builder()
+            .header(header::ContentType::TEXT_PLAIN)
+            .body(body)
     }
 
-    #[doc(hidden)]
-    #[deprecated = "Replaced by SinglePart::builder(), which chooses the best Content-Transfer-Encoding based on the provided body"]
-    pub fn quoted_printable() -> SinglePartBuilder {
-        Self::builder().header(ContentTransferEncoding::QuotedPrintable)
-    }
-
-    #[doc(hidden)]
-    #[deprecated = "Replaced by SinglePart::builder(), which chooses the best Content-Transfer-Encoding based on the provided body"]
-    pub fn base64() -> SinglePartBuilder {
-        Self::builder().header(ContentTransferEncoding::Base64)
-    }
-
-    #[doc(hidden)]
-    #[deprecated = "Replaced by SinglePart::builder(), which chooses the best Content-Transfer-Encoding based on the provided body"]
-    pub fn eight_bit() -> SinglePartBuilder {
-        Self::builder().header(ContentTransferEncoding::EightBit)
+    /// Directly create a `SinglePart` from a UTF-8 HTML content
+    pub fn html<T: IntoBody>(body: T) -> Self {
+        Self::builder()
+            .header(header::ContentType::TEXT_HTML)
+            .body(body)
     }
 
     /// Get the headers from singlepart
@@ -158,34 +142,39 @@ impl SinglePart {
         self.format(&mut out);
         out
     }
-}
 
-impl EmailFormat for SinglePart {
-    fn format(&self, out: &mut Vec<u8>) {
-        out.extend_from_slice(self.headers.to_string().as_bytes());
-        out.extend_from_slice(b"\r\n");
+    /// Format only the signlepart body
+    fn format_body(&self, out: &mut Vec<u8>) {
         out.extend_from_slice(&self.body);
         out.extend_from_slice(b"\r\n");
     }
 }
 
+impl EmailFormat for SinglePart {
+    fn format(&self, out: &mut Vec<u8>) {
+        write!(out, "{}", self.headers)
+            .expect("A Write implementation panicked while formatting headers");
+        out.extend_from_slice(b"\r\n");
+        self.format_body(out);
+    }
+}
+
 /// The kind of multipart
-///
 #[derive(Debug, Clone)]
 pub enum MultiPartKind {
     /// Mixed kind to combine unrelated content parts
     ///
-    /// For example this kind can be used to mix email message and attachments.
+    /// For example, this kind can be used to mix an email message and attachments.
     Mixed,
 
     /// Alternative kind to join several variants of same email contents.
     ///
-    /// That kind is recommended to use for joining plain (text) and rich (HTML) messages into single email message.
+    /// That kind is recommended to use for joining plain (text) and rich (HTML) messages into a single email message.
     Alternative,
 
     /// Related kind to mix content and related resources.
     ///
-    /// For example, you can include images into HTML content using that.
+    /// For example, you can include images in HTML content using that.
     Related,
 
     /// Encrypted kind for encrypted messages
@@ -196,33 +185,29 @@ pub enum MultiPartKind {
 }
 
 /// Create a random MIME boundary.
+/// (Not cryptographically random)
 fn make_boundary() -> String {
-    rand::thread_rng()
-        .sample_iter(rand::distributions::Alphanumeric)
-        .take(40)
-        .map(char::from)
-        .collect()
+    repeat_with(fastrand::alphanumeric).take(40).collect()
 }
 
 impl MultiPartKind {
-    fn to_mime<S: Into<String>>(&self, boundary: Option<S>) -> Mime {
-        let boundary = boundary.map_or_else(make_boundary, |s| s.into());
+    pub(crate) fn to_mime<S: Into<String>>(&self, boundary: Option<S>) -> Mime {
+        let boundary = boundary.map_or_else(make_boundary, Into::into);
 
-        use self::MultiPartKind::*;
         format!(
             "multipart/{}; boundary=\"{}\"{}",
             match self {
-                Mixed => "mixed",
-                Alternative => "alternative",
-                Related => "related",
-                Encrypted { .. } => "encrypted",
-                Signed { .. } => "signed",
+                Self::Mixed => "mixed",
+                Self::Alternative => "alternative",
+                Self::Related => "related",
+                Self::Encrypted { .. } => "encrypted",
+                Self::Signed { .. } => "signed",
             },
             boundary,
             match self {
-                Encrypted { protocol } => format!("; protocol=\"{}\"", protocol),
-                Signed { protocol, micalg } =>
-                    format!("; protocol=\"{}\"; micalg=\"{}\"", protocol, micalg),
+                Self::Encrypted { protocol } => format!("; protocol=\"{protocol}\""),
+                Self::Signed { protocol, micalg } =>
+                    format!("; protocol=\"{protocol}\"; micalg=\"{micalg}\""),
                 _ => String::new(),
             }
         )
@@ -231,18 +216,17 @@ impl MultiPartKind {
     }
 
     fn from_mime(m: &Mime) -> Option<Self> {
-        use self::MultiPartKind::*;
         match m.subtype().as_ref() {
-            "mixed" => Some(Mixed),
-            "alternative" => Some(Alternative),
-            "related" => Some(Related),
+            "mixed" => Some(Self::Mixed),
+            "alternative" => Some(Self::Alternative),
+            "related" => Some(Self::Related),
             "signed" => m.get_param("protocol").and_then(|p| {
-                m.get_param("micalg").map(|micalg| Signed {
+                m.get_param("micalg").map(|micalg| Self::Signed {
                     protocol: p.as_str().to_owned(),
                     micalg: micalg.as_str().to_owned(),
                 })
             }),
-            "encrypted" => m.get_param("protocol").map(|p| Encrypted {
+            "encrypted" => m.get_param("protocol").map(|p| Self::Encrypted {
                 protocol: p.as_str().to_owned(),
             }),
             _ => None,
@@ -250,14 +234,7 @@ impl MultiPartKind {
     }
 }
 
-impl From<MultiPartKind> for Mime {
-    fn from(m: MultiPartKind) -> Self {
-        m.to_mime::<String>(None)
-    }
-}
-
 /// Multipart builder
-///
 #[derive(Debug, Clone)]
 pub struct MultiPartBuilder {
     headers: Headers,
@@ -279,17 +256,17 @@ impl MultiPartBuilder {
 
     /// Set `Content-Type` header using [`MultiPartKind`]
     pub fn kind(self, kind: MultiPartKind) -> Self {
-        self.header(ContentType(kind.into()))
+        self.header(ContentType::from_mime(kind.to_mime::<String>(None)))
     }
 
     /// Set custom boundary
-    pub fn boundary<S: AsRef<str>>(self, boundary: S) -> Self {
+    pub fn boundary<S: Into<String>>(self, boundary: S) -> Self {
         let kind = {
-            let mime = &self.headers.get::<ContentType>().unwrap().0;
-            MultiPartKind::from_mime(mime).unwrap()
+            let content_type = self.headers.get::<ContentType>().unwrap();
+            MultiPartKind::from_mime(content_type.as_ref()).unwrap()
         };
-        let mime = kind.to_mime(Some(boundary.as_ref()));
-        self.header(ContentType(mime))
+        let mime = kind.to_mime(Some(boundary));
+        self.header(ContentType::from_mime(mime))
     }
 
     /// Creates multipart without parts
@@ -300,11 +277,6 @@ impl MultiPartBuilder {
         }
     }
 
-    /// Creates multipart using part
-    pub fn part(self, part: Part) -> MultiPart {
-        self.build().part(part)
-    }
-
     /// Creates multipart using singlepart
     pub fn singlepart(self, part: SinglePart) -> MultiPart {
         self.build().singlepart(part)
@@ -323,11 +295,10 @@ impl Default for MultiPartBuilder {
 }
 
 /// Multipart variant with parts
-///
 #[derive(Debug, Clone)]
 pub struct MultiPart {
     headers: Headers,
-    parts: Parts,
+    parts: Vec<Part>,
 }
 
 impl MultiPart {
@@ -371,10 +342,11 @@ impl MultiPart {
         MultiPart::builder().kind(MultiPartKind::Signed { protocol, micalg })
     }
 
-    /// Add part to multipart
-    pub fn part(mut self, part: Part) -> Self {
-        self.parts.push(part);
-        self
+    /// Alias for HTML and plain text versions of an email
+    pub fn alternative_plain_html<T: IntoBody, V: IntoBody>(plain: T, html: V) -> Self {
+        Self::alternative()
+            .singlepart(SinglePart::plain(plain))
+            .singlepart(SinglePart::html(html))
     }
 
     /// Add single part to multipart
@@ -391,8 +363,13 @@ impl MultiPart {
 
     /// Get the boundary of multipart contents
     pub fn boundary(&self) -> String {
-        let content_type = &self.headers.get::<ContentType>().unwrap().0;
-        content_type.get_param("boundary").unwrap().as_str().into()
+        let content_type = self.headers.get::<ContentType>().unwrap();
+        content_type
+            .as_ref()
+            .get_param("boundary")
+            .unwrap()
+            .as_str()
+            .into()
     }
 
     /// Get the headers from the multipart
@@ -405,29 +382,15 @@ impl MultiPart {
         &mut self.headers
     }
 
-    /// Get the parts from the multipart
-    pub fn parts(&self) -> &Parts {
-        &self.parts
-    }
-
-    /// Get a mutable reference to the parts
-    pub fn parts_mut(&mut self) -> &mut Parts {
-        &mut self.parts
-    }
-
     /// Get message content formatted for SMTP
     pub fn formatted(&self) -> Vec<u8> {
         let mut out = Vec::new();
         self.format(&mut out);
         out
     }
-}
-
-impl EmailFormat for MultiPart {
-    fn format(&self, out: &mut Vec<u8>) {
-        out.extend_from_slice(self.headers.to_string().as_bytes());
-        out.extend_from_slice(b"\r\n");
 
+    /// Format only the multipart body
+    fn format_body(&self, out: &mut Vec<u8>) {
         let boundary = self.boundary();
 
         for part in &self.parts {
@@ -443,24 +406,32 @@ impl EmailFormat for MultiPart {
     }
 }
 
+impl EmailFormat for MultiPart {
+    fn format(&self, out: &mut Vec<u8>) {
+        write!(out, "{}", self.headers)
+            .expect("A Write implementation panicked while formatting headers");
+        out.extend_from_slice(b"\r\n");
+        self.format_body(out);
+    }
+}
+
 #[cfg(test)]
 mod test {
+    use pretty_assertions::assert_eq;
+
     use super::*;
-    use crate::message::header;
 
     #[test]
     fn single_part_binary() {
         let part = SinglePart::builder()
-            .header(header::ContentType(
-                "text/plain; charset=utf8".parse().unwrap(),
-            ))
+            .header(header::ContentType::TEXT_PLAIN)
             .header(header::ContentTransferEncoding::Binary)
             .body(String::from("Текст письма в уникоде"));
 
         assert_eq!(
             String::from_utf8(part.formatted()).unwrap(),
             concat!(
-                "Content-Type: text/plain; charset=utf8\r\n",
+                "Content-Type: text/plain; charset=utf-8\r\n",
                 "Content-Transfer-Encoding: binary\r\n",
                 "\r\n",
                 "Текст письма в уникоде\r\n"
@@ -471,16 +442,14 @@ mod test {
     #[test]
     fn single_part_quoted_printable() {
         let part = SinglePart::builder()
-            .header(header::ContentType(
-                "text/plain; charset=utf8".parse().unwrap(),
-            ))
+            .header(header::ContentType::TEXT_PLAIN)
             .header(header::ContentTransferEncoding::QuotedPrintable)
             .body(String::from("Текст письма в уникоде"));
 
         assert_eq!(
             String::from_utf8(part.formatted()).unwrap(),
             concat!(
-                "Content-Type: text/plain; charset=utf8\r\n",
+                "Content-Type: text/plain; charset=utf-8\r\n",
                 "Content-Transfer-Encoding: quoted-printable\r\n",
                 "\r\n",
                 "=D0=A2=D0=B5=D0=BA=D1=81=D1=82 =D0=BF=D0=B8=D1=81=D1=8C=D0=BC=D0=B0 =D0=B2 =\r\n",
@@ -492,16 +461,14 @@ mod test {
     #[test]
     fn single_part_base64() {
         let part = SinglePart::builder()
-            .header(header::ContentType(
-                "text/plain; charset=utf8".parse().unwrap(),
-            ))
+            .header(header::ContentType::TEXT_PLAIN)
             .header(header::ContentTransferEncoding::Base64)
             .body(String::from("Текст письма в уникоде"));
 
         assert_eq!(
             String::from_utf8(part.formatted()).unwrap(),
             concat!(
-                "Content-Type: text/plain; charset=utf8\r\n",
+                "Content-Type: text/plain; charset=utf-8\r\n",
                 "Content-Transfer-Encoding: base64\r\n",
                 "\r\n",
                 "0KLQtdC60YHRgiDQv9C40YHRjNC80LAg0LIg0YPQvdC40LrQvtC00LU=\r\n"
@@ -512,75 +479,60 @@ mod test {
     #[test]
     fn multi_part_mixed() {
         let part = MultiPart::mixed()
-            .boundary("F2mTKN843loAAAAA8porEdAjCKhArPxGeahYoZYSftse1GT/84tup+O0bs8eueVuAlMK")
-            .part(Part::Single(
-                SinglePart::builder()
-                    .header(header::ContentType(
-                        "text/plain; charset=utf8".parse().unwrap(),
-                    ))
-                    .header(header::ContentTransferEncoding::Binary)
-                    .body(String::from("Текст письма в уникоде")),
-            ))
+            .boundary("0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1")
             .singlepart(
                 SinglePart::builder()
-                    .header(header::ContentType(
-                        "text/plain; charset=utf8".parse().unwrap(),
-                    ))
-                    .header(header::ContentDisposition {
-                        disposition: header::DispositionType::Attachment,
-                        parameters: vec![header::DispositionParam::Filename(
-                            header::Charset::Ext("utf-8".into()),
-                            None,
-                            "example.c".into(),
-                        )],
-                    })
+                    .header(header::ContentType::TEXT_PLAIN)
+                    .header(header::ContentTransferEncoding::Binary)
+                    .body(String::from("Текст письма в уникоде")),
+            )
+            .singlepart(
+                SinglePart::builder()
+                    .header(header::ContentType::TEXT_PLAIN)
+                    .header(header::ContentDisposition::attachment("example.c"))
                     .header(header::ContentTransferEncoding::Binary)
                     .body(String::from("int main() { return 0; }")),
             );
 
-        assert_eq!(String::from_utf8(part.formatted()).unwrap(),
-                   concat!("Content-Type: multipart/mixed;",
-                           " boundary=\"F2mTKN843loAAAAA8porEdAjCKhArPxGeahYoZYSftse1GT/84tup+O0bs8eueVuAlMK\"\r\n",
-                           "\r\n",
-                           "--F2mTKN843loAAAAA8porEdAjCKhArPxGeahYoZYSftse1GT/84tup+O0bs8eueVuAlMK\r\n",
-                           "Content-Type: text/plain; charset=utf8\r\n",
-                           "Content-Transfer-Encoding: binary\r\n",
-                           "\r\n",
-                           "Текст письма в уникоде\r\n",
-                           "--F2mTKN843loAAAAA8porEdAjCKhArPxGeahYoZYSftse1GT/84tup+O0bs8eueVuAlMK\r\n",
-                           "Content-Type: text/plain; charset=utf8\r\n",
-                           "Content-Disposition: attachment; filename=\"example.c\"\r\n",
-                           "Content-Transfer-Encoding: binary\r\n",
-                           "\r\n",
-                           "int main() { return 0; }\r\n",
-                           "--F2mTKN843loAAAAA8porEdAjCKhArPxGeahYoZYSftse1GT/84tup+O0bs8eueVuAlMK--\r\n"));
+        assert_eq!(
+            String::from_utf8(part.formatted()).unwrap(),
+            concat!(
+                "Content-Type: multipart/mixed;\r\n",
+                " boundary=\"0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\"\r\n",
+                "\r\n",
+                "--0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\r\n",
+                "Content-Type: text/plain; charset=utf-8\r\n",
+                "Content-Transfer-Encoding: binary\r\n",
+                "\r\n",
+                "Текст письма в уникоде\r\n",
+                "--0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\r\n",
+                "Content-Type: text/plain; charset=utf-8\r\n",
+                "Content-Disposition: attachment; filename=\"example.c\"\r\n",
+                "Content-Transfer-Encoding: binary\r\n",
+                "\r\n",
+                "int main() { return 0; }\r\n",
+                "--0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1--\r\n"
+            )
+        );
     }
     #[test]
     fn multi_part_encrypted() {
         let part = MultiPart::encrypted("application/pgp-encrypted".to_owned())
-            .boundary("F2mTKN843loAAAAA8porEdAjCKhArPxGeahYoZYSftse1GT/84tup+O0bs8eueVuAlMK")
-            .part(Part::Single(
-                SinglePart::builder()
-                    .header(header::ContentType(
-                        "application/pgp-encrypted".parse().unwrap(),
-                    ))
-                    .body(String::from("Version: 1")),
-            ))
+            .boundary("0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1")
             .singlepart(
                 SinglePart::builder()
-                    .header(ContentType(
-                        "application/octet-stream; name=\"encrypted.asc\""
-                            .parse()
+                    .header(header::ContentType::parse("application/pgp-encrypted").unwrap())
+                    .body(String::from("Version: 1")),
+            )
+            .singlepart(
+                SinglePart::builder()
+                    .header(
+                        ContentType::parse("application/octet-stream; name=\"encrypted.asc\"")
                             .unwrap(),
+                    )
+                    .header(header::ContentDisposition::inline_with_name(
+                        "encrypted.asc",
                     ))
-                    .header(header::ContentDisposition {
-                        disposition: header::DispositionType::Inline,
-                        parameters: vec![header::DispositionParam::Filename(
-                            header::Charset::Ext("utf-8".into()),
-                            None,
-                            "encrypted.asc".into(),
-                        )],
-                    })
                     .body(String::from(concat!(
                         "-----BEGIN PGP MESSAGE-----\r\n",
                         "wV4D0dz5vDXklO8SAQdA5lGX1UU/eVQqDxNYdHa7tukoingHzqUB6wQssbMfHl8w\r\n",
@@ -589,27 +541,31 @@ mod test {
                     ))),
             );
 
-        assert_eq!(String::from_utf8(part.formatted()).unwrap(),
-                   concat!("Content-Type: multipart/encrypted;",
-                           " boundary=\"F2mTKN843loAAAAA8porEdAjCKhArPxGeahYoZYSftse1GT/84tup+O0bs8eueVuAlMK\";",
-                           " protocol=\"application/pgp-encrypted\"\r\n",
-                           "\r\n",
-                           "--F2mTKN843loAAAAA8porEdAjCKhArPxGeahYoZYSftse1GT/84tup+O0bs8eueVuAlMK\r\n",
-                           "Content-Type: application/pgp-encrypted\r\n",
-                           "Content-Transfer-Encoding: 7bit\r\n",
-                           "\r\n",
-                           "Version: 1\r\n",
-                           "--F2mTKN843loAAAAA8porEdAjCKhArPxGeahYoZYSftse1GT/84tup+O0bs8eueVuAlMK\r\n",
-                           "Content-Type: application/octet-stream; name=\"encrypted.asc\"\r\n",
-                           "Content-Disposition: inline; filename=\"encrypted.asc\"\r\n",
-                           "Content-Transfer-Encoding: 7bit\r\n",
-                           "\r\n",
-                           "-----BEGIN PGP MESSAGE-----\r\n",
-                           "wV4D0dz5vDXklO8SAQdA5lGX1UU/eVQqDxNYdHa7tukoingHzqUB6wQssbMfHl8w\r\n",
-                           "...\r\n",
-                           "-----END PGP MESSAGE-----\r\n",
-                           "\r\n",
-                           "--F2mTKN843loAAAAA8porEdAjCKhArPxGeahYoZYSftse1GT/84tup+O0bs8eueVuAlMK--\r\n"));
+        assert_eq!(
+            String::from_utf8(part.formatted()).unwrap(),
+            concat!(
+                "Content-Type: multipart/encrypted;\r\n",
+                " boundary=\"0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\";\r\n",
+                " protocol=\"application/pgp-encrypted\"\r\n",
+                "\r\n",
+                "--0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\r\n",
+                "Content-Type: application/pgp-encrypted\r\n",
+                "Content-Transfer-Encoding: 7bit\r\n",
+                "\r\n",
+                "Version: 1\r\n",
+                "--0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\r\n",
+                "Content-Type: application/octet-stream; name=\"encrypted.asc\"\r\n",
+                "Content-Disposition: inline; filename=\"encrypted.asc\"\r\n",
+                "Content-Transfer-Encoding: 7bit\r\n",
+                "\r\n",
+                "-----BEGIN PGP MESSAGE-----\r\n",
+                "wV4D0dz5vDXklO8SAQdA5lGX1UU/eVQqDxNYdHa7tukoingHzqUB6wQssbMfHl8w\r\n",
+                "...\r\n",
+                "-----END PGP MESSAGE-----\r\n",
+                "\r\n",
+                "--0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1--\r\n"
+            )
+        );
     }
     #[test]
     fn multi_part_signed() {
@@ -617,27 +573,19 @@ mod test {
             "application/pgp-signature".to_owned(),
             "pgp-sha256".to_owned(),
         )
-        .boundary("F2mTKN843loAAAAA8porEdAjCKhArPxGeahYoZYSftse1GT/84tup+O0bs8eueVuAlMK")
-        .part(Part::Single(
-            SinglePart::builder()
-                .header(header::ContentType("text/plain".parse().unwrap()))
-                .body(String::from("Test email for signature")),
-        ))
+        .boundary("0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1")
         .singlepart(
             SinglePart::builder()
-                .header(ContentType(
-                    "application/pgp-signature; name=\"signature.asc\""
-                        .parse()
+                .header(header::ContentType::TEXT_PLAIN)
+                .body(String::from("Test email for signature")),
+        )
+        .singlepart(
+            SinglePart::builder()
+                .header(
+                    ContentType::parse("application/pgp-signature; name=\"signature.asc\"")
                         .unwrap(),
-                ))
-                .header(header::ContentDisposition {
-                    disposition: header::DispositionType::Attachment,
-                    parameters: vec![header::DispositionParam::Filename(
-                        header::Charset::Ext("utf-8".into()),
-                        None,
-                        "signature.asc".into(),
-                    )],
-                })
+                )
+                .header(header::ContentDisposition::attachment("signature.asc"))
                 .body(String::from(concat!(
                     "-----BEGIN PGP SIGNATURE-----\r\n",
                     "\r\n",
@@ -649,101 +597,102 @@ mod test {
                 ))),
         );
 
-        assert_eq!(String::from_utf8(part.formatted()).unwrap(),
-                   concat!("Content-Type: multipart/signed;",
-                           " boundary=\"F2mTKN843loAAAAA8porEdAjCKhArPxGeahYoZYSftse1GT/84tup+O0bs8eueVuAlMK\";",
-                           " protocol=\"application/pgp-signature\";",
-                           " micalg=\"pgp-sha256\"\r\n",
-                           "\r\n",
-                           "--F2mTKN843loAAAAA8porEdAjCKhArPxGeahYoZYSftse1GT/84tup+O0bs8eueVuAlMK\r\n",
-                           "Content-Type: text/plain\r\n",
-                           "Content-Transfer-Encoding: 7bit\r\n",
-                           "\r\n",
-                           "Test email for signature\r\n",
-                           "--F2mTKN843loAAAAA8porEdAjCKhArPxGeahYoZYSftse1GT/84tup+O0bs8eueVuAlMK\r\n",
-                           "Content-Type: application/pgp-signature; name=\"signature.asc\"\r\n",
-                           "Content-Disposition: attachment; filename=\"signature.asc\"\r\n",
-                           "Content-Transfer-Encoding: 7bit\r\n",
-                           "\r\n",
-                           "-----BEGIN PGP SIGNATURE-----\r\n",
-                            "\r\n",
-                            "iHUEARYIAB0WIQTNsp3S/GbdE0KoiQ+IGQOscREZuQUCXyOzDAAKCRCIGQOscREZ\r\n",
-                            "udgDAQCv3FJ3QWW5bRaGZAa0Ug6vASFdkvDMKoRwcoFnHPthjQEAiQ8skkIyE2GE\r\n",
-                            "PoLpAXiKpT+NU8S8+8dfvwutnb4dSwM=\r\n",
-                            "=3FYZ\r\n",
-                            "-----END PGP SIGNATURE-----\r\n",
-                           "\r\n",
-                           "--F2mTKN843loAAAAA8porEdAjCKhArPxGeahYoZYSftse1GT/84tup+O0bs8eueVuAlMK--\r\n"));
+        assert_eq!(
+            String::from_utf8(part.formatted()).unwrap(),
+            concat!(
+                "Content-Type: multipart/signed;\r\n",
+                " boundary=\"0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\";\r\n",
+                " protocol=\"application/pgp-signature\";",
+                " micalg=\"pgp-sha256\"\r\n",
+                "\r\n",
+                "--0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\r\n",
+                "Content-Type: text/plain; charset=utf-8\r\n",
+                "Content-Transfer-Encoding: 7bit\r\n",
+                "\r\n",
+                "Test email for signature\r\n",
+                "--0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\r\n",
+                "Content-Type: application/pgp-signature; name=\"signature.asc\"\r\n",
+                "Content-Disposition: attachment; filename=\"signature.asc\"\r\n",
+                "Content-Transfer-Encoding: 7bit\r\n",
+                "\r\n",
+                "-----BEGIN PGP SIGNATURE-----\r\n",
+                "\r\n",
+                "iHUEARYIAB0WIQTNsp3S/GbdE0KoiQ+IGQOscREZuQUCXyOzDAAKCRCIGQOscREZ\r\n",
+                "udgDAQCv3FJ3QWW5bRaGZAa0Ug6vASFdkvDMKoRwcoFnHPthjQEAiQ8skkIyE2GE\r\n",
+                "PoLpAXiKpT+NU8S8+8dfvwutnb4dSwM=\r\n",
+                "=3FYZ\r\n",
+                "-----END PGP SIGNATURE-----\r\n",
+                "\r\n",
+                "--0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1--\r\n"
+            )
+        );
     }
 
     #[test]
     fn multi_part_alternative() {
         let part = MultiPart::alternative()
-            .boundary("F2mTKN843loAAAAA8porEdAjCKhArPxGeahYoZYSftse1GT/84tup+O0bs8eueVuAlMK")
-            .part(Part::Single(SinglePart::builder()
-                             .header(header::ContentType("text/plain; charset=utf8".parse().unwrap()))
-                             .header(header::ContentTransferEncoding::Binary)
-                             .body(String::from("Текст письма в уникоде"))))
+            .boundary("0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1")
             .singlepart(SinglePart::builder()
-                             .header(header::ContentType("text/html; charset=utf8".parse().unwrap()))
+                             .header(header::ContentType::TEXT_PLAIN)
+                             .header(header::ContentTransferEncoding::Binary)
+                             .body(String::from("Текст письма в уникоде")))
+            .singlepart(SinglePart::builder()
+                             .header(header::ContentType::TEXT_HTML)
                              .header(header::ContentTransferEncoding::Binary)
                              .body(String::from("<p>Текст <em>письма</em> в <a href=\"https://ru.wikipedia.org/wiki/Юникод\">уникоде</a><p>")));
 
         assert_eq!(String::from_utf8(part.formatted()).unwrap(),
-                   concat!("Content-Type: multipart/alternative;",
-                           " boundary=\"F2mTKN843loAAAAA8porEdAjCKhArPxGeahYoZYSftse1GT/84tup+O0bs8eueVuAlMK\"\r\n",
+                   concat!("Content-Type: multipart/alternative;\r\n",
+                           " boundary=\"0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\"\r\n",
                            "\r\n",
-                           "--F2mTKN843loAAAAA8porEdAjCKhArPxGeahYoZYSftse1GT/84tup+O0bs8eueVuAlMK\r\n",
-                           "Content-Type: text/plain; charset=utf8\r\n",
+                           "--0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\r\n",
+                           "Content-Type: text/plain; charset=utf-8\r\n",
                            "Content-Transfer-Encoding: binary\r\n",
                            "\r\n",
                            "Текст письма в уникоде\r\n",
-                           "--F2mTKN843loAAAAA8porEdAjCKhArPxGeahYoZYSftse1GT/84tup+O0bs8eueVuAlMK\r\n",
-                           "Content-Type: text/html; charset=utf8\r\n",
+                           "--0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\r\n",
+                           "Content-Type: text/html; charset=utf-8\r\n",
                            "Content-Transfer-Encoding: binary\r\n",
                            "\r\n",
                            "<p>Текст <em>письма</em> в <a href=\"https://ru.wikipedia.org/wiki/Юникод\">уникоде</a><p>\r\n",
-                           "--F2mTKN843loAAAAA8porEdAjCKhArPxGeahYoZYSftse1GT/84tup+O0bs8eueVuAlMK--\r\n"));
+                           "--0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1--\r\n"));
     }
 
     #[test]
     fn multi_part_mixed_related() {
         let part = MultiPart::mixed()
-            .boundary("F2mTKN843loAAAAA8porEdAjCKhArPxGeahYoZYSftse1GT/84tup+O0bs8eueVuAlMK")
+            .boundary("0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1")
             .multipart(MultiPart::related()
-                            .boundary("E912L4JH3loAAAAAFu/33Gx7PEoTMmhGaxG3FlbVMQHctj96q4nHvBM+7DTtXo/im8gh")
+                            .boundary("0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1")
                             .singlepart(SinglePart::builder()
-                                             .header(header::ContentType("text/html; charset=utf8".parse().unwrap()))
+                                             .header(header::ContentType::TEXT_HTML)
                                              .header(header::ContentTransferEncoding::Binary)
                                              .body(String::from("<p>Текст <em>письма</em> в <a href=\"https://ru.wikipedia.org/wiki/Юникод\">уникоде</a><p>")))
                             .singlepart(SinglePart::builder()
-                                             .header(header::ContentType("image/png".parse().unwrap()))
-                                             .header(header::ContentLocation("/image.png".into()))
+                                             .header(header::ContentType::parse("image/png").unwrap())
+                                             .header(header::ContentLocation::from(String::from("/image.png")))
                                              .header(header::ContentTransferEncoding::Base64)
                                              .body(String::from("1234567890123456789012345678901234567890123456789012345678901234567890123456789012345678901234567890123456789012345678901234567890"))))
             .singlepart(SinglePart::builder()
-                             .header(header::ContentType("text/plain; charset=utf8".parse().unwrap()))
-                             .header(header::ContentDisposition {
-                                 disposition: header::DispositionType::Attachment,
-                                 parameters: vec![header::DispositionParam::Filename(header::Charset::Ext("utf-8".into()), None, "example.c".into())]
-                             })
+                             .header(header::ContentType::TEXT_PLAIN)
+                             .header(header::ContentDisposition::attachment("example.c"))
                              .header(header::ContentTransferEncoding::Binary)
                              .body(String::from("int main() { return 0; }")));
 
         assert_eq!(String::from_utf8(part.formatted()).unwrap(),
-                   concat!("Content-Type: multipart/mixed;",
-                           " boundary=\"F2mTKN843loAAAAA8porEdAjCKhArPxGeahYoZYSftse1GT/84tup+O0bs8eueVuAlMK\"\r\n",
+                   concat!("Content-Type: multipart/mixed;\r\n",
+                           " boundary=\"0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\"\r\n",
                            "\r\n",
-                           "--F2mTKN843loAAAAA8porEdAjCKhArPxGeahYoZYSftse1GT/84tup+O0bs8eueVuAlMK\r\n",
-                           "Content-Type: multipart/related;",
-                           " boundary=\"E912L4JH3loAAAAAFu/33Gx7PEoTMmhGaxG3FlbVMQHctj96q4nHvBM+7DTtXo/im8gh\"\r\n",
+                           "--0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\r\n",
+                           "Content-Type: multipart/related;\r\n",
+                           " boundary=\"0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\"\r\n",
                            "\r\n",
-                           "--E912L4JH3loAAAAAFu/33Gx7PEoTMmhGaxG3FlbVMQHctj96q4nHvBM+7DTtXo/im8gh\r\n",
-                           "Content-Type: text/html; charset=utf8\r\n",
+                           "--0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\r\n",
+                           "Content-Type: text/html; charset=utf-8\r\n",
                            "Content-Transfer-Encoding: binary\r\n",
                            "\r\n",
                            "<p>Текст <em>письма</em> в <a href=\"https://ru.wikipedia.org/wiki/Юникод\">уникоде</a><p>\r\n",
-                           "--E912L4JH3loAAAAAFu/33Gx7PEoTMmhGaxG3FlbVMQHctj96q4nHvBM+7DTtXo/im8gh\r\n",
+                           "--0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\r\n",
                            "Content-Type: image/png\r\n",
                            "Content-Location: /image.png\r\n",
                            "Content-Transfer-Encoding: base64\r\n",
@@ -751,14 +700,14 @@ mod test {
                            "MTIzNDU2Nzg5MDEyMzQ1Njc4OTAxMjM0NTY3ODkwMTIzNDU2Nzg5MDEyMzQ1Njc4OTAxMjM0NTY3\r\n",
                            "ODkwMTIzNDU2Nzg5MDEyMzQ1Njc4OTAxMjM0NTY3ODkwMTIzNDU2Nzg5MDEyMzQ1Njc4OTAxMjM0\r\n",
                            "NTY3ODkwMTIzNDU2Nzg5MA==\r\n",
-                           "--E912L4JH3loAAAAAFu/33Gx7PEoTMmhGaxG3FlbVMQHctj96q4nHvBM+7DTtXo/im8gh--\r\n",
-                           "--F2mTKN843loAAAAA8porEdAjCKhArPxGeahYoZYSftse1GT/84tup+O0bs8eueVuAlMK\r\n",
-                           "Content-Type: text/plain; charset=utf8\r\n",
+                           "--0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1--\r\n",
+                           "--0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\r\n",
+                           "Content-Type: text/plain; charset=utf-8\r\n",
                            "Content-Disposition: attachment; filename=\"example.c\"\r\n",
                            "Content-Transfer-Encoding: binary\r\n",
                            "\r\n",
                            "int main() { return 0; }\r\n",
-                           "--F2mTKN843loAAAAA8porEdAjCKhArPxGeahYoZYSftse1GT/84tup+O0bs8eueVuAlMK--\r\n"));
+                           "--0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1--\r\n"));
     }
 
     #[test]

src/message/mod.rs

@@ -4,15 +4,8 @@
 //!
 //! This section demonstrates how to build messages.
 //!
-//! <!--
-//! style for <details><summary>Blablabla</summary> Lots of stuff</details>
-//! borrowed from https://docs.rs/time/0.2.23/src/time/lib.rs.html#49-54
-//! -->
 //! <style>
 //! summary, details:not([open]) { cursor: pointer; }
-//! summary { display: list-item; }
-//! summary::marker { content: '▶ '; }
-//! details[open] summary::marker { content: '▼ '; }
 //! </style>
 //!
 //!
@@ -21,7 +14,7 @@
 //! The easiest way of creating a message, which uses a plain text body.
 //!
 //! ```rust
-//! use lettre::message::Message;
+//! use lettre::message::{header::ContentType, Message};
 //!
 //! # use std::error::Error;
 //! # fn main() -> Result<(), Box<dyn Error>> {
@@ -30,6 +23,7 @@
 //!     .reply_to("Yuin <yuin@domain.tld>".parse()?)
 //!     .to("Hei <hei@domain.tld>".parse()?)
 //!     .subject("Happy new year")
+//!     .header(ContentType::TEXT_PLAIN)
 //!     .body(String::from("Be happy!"))?;
 //! # Ok(())
 //! # }
@@ -45,6 +39,7 @@
 //! To: Hei <hei@domain.tld>
 //! Subject: Happy new year
 //! Date: Sat, 12 Dec 2020 16:33:19 GMT
+//! Content-Type: text/plain; charset=utf-8
 //! Content-Transfer-Encoding: 7bit
 //!
 //! Be happy!
@@ -63,7 +58,7 @@
 //!
 //! ```rust
 //! # use std::error::Error;
-//! use lettre::message::{header, Message, MultiPart, Part, SinglePart};
+//! use lettre::message::{header, Message, MultiPart, SinglePart};
 //!
 //! # fn main() -> Result<(), Box<dyn Error>> {
 //! let m = Message::builder()
@@ -71,21 +66,10 @@
 //!     .reply_to("Yuin <yuin@domain.tld>".parse()?)
 //!     .to("Hei <hei@domain.tld>".parse()?)
 //!     .subject("Happy new year")
-//!     .multipart(
-//!         MultiPart::alternative()
-//!             .singlepart(
-//!                 SinglePart::builder()
-//!                     .header(header::ContentType("text/plain; charset=utf8".parse()?))
-//!                     .body(String::from("Hello, world! :)")),
-//!             )
-//!             .singlepart(
-//!                 SinglePart::builder()
-//!                     .header(header::ContentType("text/html; charset=utf8".parse()?))
-//!                     .body(String::from(
-//!                         "<p><b>Hello</b>, <i>world</i>! <img src=\"cid:123\"></p>",
-//!                     )),
-//!             ),
-//!     )?;
+//!     .multipart(MultiPart::alternative_plain_html(
+//!         String::from("Hello, world! :)"),
+//!         String::from("<p><b>Hello</b>, <i>world</i>! <img src=\"cid:123\"></p>"),
+//!     ))?;
 //! # Ok(())
 //! # }
 //! ```
@@ -114,7 +98,6 @@
 //!
 //! <p><b>Hello</b>, <i>world</i>! <img src="cid:123"></p>
 //! --0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1--
-//!
 //! ```
 //! </details>
 //!
@@ -126,7 +109,8 @@
 //! ```rust
 //! # use std::error::Error;
 //! use std::fs;
-//! use lettre::message::{Body, header, Message, MultiPart, Part, SinglePart};
+//!
+//! use lettre::message::{header, Attachment, Body, Message, MultiPart, SinglePart};
 //!
 //! # fn main() -> Result<(), Box<dyn Error>> {
 //! let image = fs::read("docs/lettre.png")?;
@@ -145,47 +129,22 @@
 //!         MultiPart::mixed()
 //!             .multipart(
 //!                 MultiPart::alternative()
-//!                     .singlepart(
-//!                         SinglePart::builder()
-//!                             .header(header::ContentType("text/plain; charset=utf8".parse()?))
-//!                             .body(String::from("Hello, world! :)")),
-//!                     )
+//!                     .singlepart(SinglePart::plain(String::from("Hello, world! :)")))
 //!                     .multipart(
 //!                         MultiPart::related()
+//!                             .singlepart(SinglePart::html(String::from(
+//!                                 "<p><b>Hello</b>, <i>world</i>! <img src=cid:123></p>",
+//!                             )))
 //!                             .singlepart(
-//!                                 SinglePart::builder()
-//!                                     .header(header::ContentType(
-//!                                         "text/html; charset=utf8".parse()?,
-//!                                     ))
-//!                                     .body(String::from(
-//!                                         "<p><b>Hello</b>, <i>world</i>! <img src=cid:123></p>",
-//!                                     )),
-//!                             )
-//!                             .singlepart(
-//!                                 SinglePart::builder()
-//!                                     .header(header::ContentType("image/png".parse()?))
-//!                                     .header(header::ContentDisposition {
-//!                                         disposition: header::DispositionType::Inline,
-//!                                         parameters: vec![],
-//!                                     })
-//!                                     .header(header::ContentId("<123>".into()))
-//!                                     .body(image_body),
+//!                                 Attachment::new_inline(String::from("123"))
+//!                                     .body(image_body, "image/png".parse().unwrap()),
 //!                             ),
 //!                     ),
 //!             )
-//!             .singlepart(
-//!                 SinglePart::builder()
-//!                     .header(header::ContentType("text/plain; charset=utf8".parse()?))
-//!                     .header(header::ContentDisposition {
-//!                         disposition: header::DispositionType::Attachment,
-//!                         parameters: vec![header::DispositionParam::Filename(
-//!                             header::Charset::Ext("utf-8".into()),
-//!                             None,
-//!                             "example.rs".as_bytes().into(),
-//!                         )],
-//!                     })
-//!                     .body(String::from("fn main() { println!(\"Hello, World!\") }")),
-//!             ),
+//!             .singlepart(Attachment::new(String::from("example.rs")).body(
+//!                 String::from("fn main() { println!(\"Hello, World!\") }"),
+//!                 "text/plain".parse().unwrap(),
+//!             )),
 //!     )?;
 //! # Ok(())
 //! # }
@@ -236,36 +195,36 @@
 //!
 //! fn main() { println!("Hello, World!") }
 //! --0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1--
-//!
 //! ```
 //! </details>
 
+use std::{io::Write, iter, time::SystemTime};
+
+pub use attachment::Attachment;
 pub use body::{Body, IntoBody, MaybeString};
+#[cfg(feature = "dkim")]
+pub use dkim::*;
 pub use mailbox::*;
 pub use mimebody::*;
 
-pub use mime;
-
+mod attachment;
 mod body;
+#[cfg(feature = "dkim")]
+pub mod dkim;
 pub mod header;
 mod mailbox;
 mod mimebody;
-mod utf8_b;
-
-use std::convert::TryFrom;
-use std::time::SystemTime;
-
-use uuid::Uuid;
 
 use crate::{
     address::Envelope,
-    message::header::{ContentTransferEncoding, EmailDate, Header, Headers, MailboxesHeader},
+    message::header::{ContentTransferEncoding, Header, Headers, MailboxesHeader},
     Error as EmailError,
 };
 
 const DEFAULT_MESSAGE_ID_DOMAIN: &str = "localhost";
 
-pub trait EmailFormat {
+/// Something that can be formatted as an email message
+trait EmailFormat {
     // Use a writer?
     fn format(&self, out: &mut Vec<u8>);
 }
@@ -275,6 +234,7 @@ pub trait EmailFormat {
 pub struct MessageBuilder {
     headers: Headers,
     envelope: Option<Envelope>,
+    drop_bcc: bool,
 }
 
 impl MessageBuilder {
@@ -283,76 +243,46 @@ impl MessageBuilder {
         Self {
             headers: Headers::new(),
             envelope: None,
+            drop_bcc: true,
         }
     }
 
-    /// Set custom header to message
-    pub fn header<H: Header>(mut self, header: H) -> Self {
-        self.headers.set(header);
-        self
-    }
-
-    /// Add mailbox to header
-    pub fn mailbox<H: Header + MailboxesHeader>(mut self, header: H) -> Self {
-        if self.headers.has::<H>() {
-            self.headers.get_mut::<H>().unwrap().join_mailboxes(header);
-            self
-        } else {
-            self.header(header)
-        }
-    }
-
-    /// Add `Date` header to message
-    ///
-    /// Shortcut for `self.header(header::Date(date))`.
-    pub fn date(self, date: EmailDate) -> Self {
-        self.header(header::Date(date))
-    }
-
-    /// Set `Date` header using current date/time
-    ///
-    /// Shortcut for `self.date(SystemTime::now())`.
-    pub fn date_now(self) -> Self {
-        self.date(SystemTime::now().into())
-    }
-
-    /// Set `Subject` header to message
-    ///
-    /// Shortcut for `self.header(header::Subject(subject.into()))`.
-    pub fn subject<S: Into<String>>(self, subject: S) -> Self {
-        self.header(header::Subject(subject.into()))
-    }
-
-    /// Set `Mime-Version` header to 1.0
-    ///
-    /// Shortcut for `self.header(header::MIME_VERSION_1_0)`.
-    ///
-    /// Not exposed as it is set by body methods
-    fn mime_1_0(self) -> Self {
-        self.header(header::MIME_VERSION_1_0)
-    }
-
-    /// Set `Sender` header. Should be used when providing several `From` mailboxes.
-    ///
-    /// https://tools.ietf.org/html/rfc5322#section-3.6.2
-    ///
-    /// Shortcut for `self.header(header::Sender(mbox))`.
-    pub fn sender(self, mbox: Mailbox) -> Self {
-        self.header(header::Sender(mbox))
-    }
-
     /// Set or add mailbox to `From` header
     ///
-    /// https://tools.ietf.org/html/rfc5322#section-3.6.2
+    /// Defined in [RFC5322](https://tools.ietf.org/html/rfc5322#section-3.6.2).
     ///
     /// Shortcut for `self.mailbox(header::From(mbox))`.
     pub fn from(self, mbox: Mailbox) -> Self {
-        self.mailbox(header::From(mbox.into()))
+        self.mailbox(header::From::from(Mailboxes::from(mbox)))
+    }
+
+    /// Set `Sender` header. Should be used when providing several `From` mailboxes.
+    ///
+    /// Defined in [RFC5322](https://tools.ietf.org/html/rfc5322#section-3.6.2).
+    ///
+    /// Shortcut for `self.header(header::Sender(mbox))`.
+    pub fn sender(self, mbox: Mailbox) -> Self {
+        self.header(header::Sender::from(mbox))
+    }
+
+    /// Add `Date` header to message
+    ///
+    /// Shortcut for `self.header(header::Date::new(st))`.
+    pub fn date(self, st: SystemTime) -> Self {
+        self.header(header::Date::new(st))
+    }
+
+    /// Set `Date` header using current date/time
+    ///
+    /// Shortcut for `self.date(SystemTime::now())`, it is automatically inserted
+    /// if no date has been provided.
+    pub fn date_now(self) -> Self {
+        self.date(crate::time::now())
     }
 
     /// Set or add mailbox to `ReplyTo` header
     ///
-    /// https://tools.ietf.org/html/rfc5322#section-3.6.2
+    /// Defined in [RFC5322](https://tools.ietf.org/html/rfc5322#section-3.6.2).
     ///
     /// Shortcut for `self.mailbox(header::ReplyTo(mbox))`.
     pub fn reply_to(self, mbox: Mailbox) -> Self {
@@ -383,16 +313,24 @@ impl MessageBuilder {
     /// Set or add message id to [`In-Reply-To`
     /// header](https://tools.ietf.org/html/rfc5322#section-3.6.4)
     pub fn in_reply_to(self, id: String) -> Self {
-        self.header(header::InReplyTo(id))
+        self.header(header::InReplyTo::from(id))
     }
 
     /// Set or add message id to [`References`
     /// header](https://tools.ietf.org/html/rfc5322#section-3.6.4)
     pub fn references(self, id: String) -> Self {
-        self.header(header::References(id))
+        self.header(header::References::from(id))
     }
 
-    /// Set [Message-Id
+    /// Set `Subject` header to message
+    ///
+    /// Shortcut for `self.header(header::Subject(subject.into()))`.
+    pub fn subject<S: Into<String>>(self, subject: S) -> Self {
+        let s: String = subject.into();
+        self.header(header::Subject::from(s))
+    }
+
+    /// Set [Message-ID
     /// header](https://tools.ietf.org/html/rfc5322#section-3.6.4)
     ///
     /// Should generally be inserted by the mail relay.
@@ -401,28 +339,45 @@ impl MessageBuilder {
     /// `<UUID@HOSTNAME>`.
     pub fn message_id(self, id: Option<String>) -> Self {
         match id {
-            Some(i) => self.header(header::MessageId(i)),
+            Some(i) => self.header(header::MessageId::from(i)),
             None => {
                 #[cfg(feature = "hostname")]
                 let hostname = hostname::get()
                     .map_err(|_| ())
                     .and_then(|s| s.into_string().map_err(|_| ()))
-                    .unwrap_or_else(|_| DEFAULT_MESSAGE_ID_DOMAIN.to_string());
+                    .unwrap_or_else(|()| DEFAULT_MESSAGE_ID_DOMAIN.to_owned());
                 #[cfg(not(feature = "hostname"))]
-                let hostname = DEFAULT_MESSAGE_ID_DOMAIN.to_string();
+                let hostname = DEFAULT_MESSAGE_ID_DOMAIN.to_owned();
 
-                self.header(header::MessageId(
+                self.header(header::MessageId::from(
                     // https://tools.ietf.org/html/rfc5322#section-3.6.4
-                    format!("<{}@{}>", Uuid::new_v4(), hostname),
+                    format!("<{}@{}>", make_message_id(), hostname),
                 ))
             }
         }
     }
 
     /// Set [User-Agent
-    /// header](https://tools.ietf.org/html/draft-melnikov-email-user-agent-004)
+    /// header](https://tools.ietf.org/html/draft-melnikov-email-user-agent-00)
     pub fn user_agent(self, id: String) -> Self {
-        self.header(header::UserAgent(id))
+        self.header(header::UserAgent::from(id))
+    }
+
+    /// Set custom header to message
+    pub fn header<H: Header>(mut self, header: H) -> Self {
+        self.headers.set(header);
+        self
+    }
+
+    /// Add mailbox to header
+    pub fn mailbox<H: Header + MailboxesHeader>(self, header: H) -> Self {
+        match self.headers.get::<H>() {
+            Some(mut header_) => {
+                header_.join_mailboxes(header);
+                self.header(header_)
+            }
+            None => self.header(header),
+        }
     }
 
     /// Force specific envelope (by default it is derived from headers)
@@ -431,6 +386,20 @@ impl MessageBuilder {
         self
     }
 
+    /// Keep the `Bcc` header
+    ///
+    /// By default, the `Bcc` header is removed from the email after
+    /// using it to generate the message envelope. In some cases though,
+    /// like when saving the email as an `.eml`, or sending through
+    /// some transports (like the Gmail API) that don't take a separate
+    /// envelope value, it becomes necessary to keep the `Bcc` header.
+    ///
+    /// Calling this method overrides the default behavior.
+    pub fn keep_bcc(mut self) -> Self {
+        self.drop_bcc = false;
+        self
+    }
+
     // TODO: High-level methods for attachments and embedded files
 
     /// Create message from body
@@ -439,7 +408,7 @@ impl MessageBuilder {
         // https://tools.ietf.org/html/rfc5322#section-3.6
 
         // Insert Date if missing
-        let res = if self.headers.get::<header::Date>().is_none() {
+        let mut res = if self.headers.get::<header::Date>().is_none() {
             self.date_now()
         } else {
             self
@@ -448,7 +417,7 @@ impl MessageBuilder {
         // Fail is missing correct originator (Sender or From)
         match res.headers.get::<header::From>() {
             Some(header::From(f)) => {
-                let from: Vec<Mailbox> = f.clone().into();
+                let from: Vec<Mailbox> = f.into();
                 if from.len() > 1 && res.headers.get::<header::Sender>().is_none() {
                     return Err(EmailError::TooManyFrom);
                 }
@@ -462,6 +431,12 @@ impl MessageBuilder {
             Some(e) => e,
             None => Envelope::try_from(&res.headers)?,
         };
+
+        if res.drop_bcc {
+            // Remove `Bcc` headers now the envelope is set
+            res.headers.remove::<header::Bcc>();
+        }
+
         Ok(Message {
             headers: res.headers,
             body,
@@ -475,25 +450,35 @@ impl MessageBuilder {
     /// `Content-Transfer-Encoding`, based on the most efficient and valid encoding
     /// for `body`.
     pub fn body<T: IntoBody>(mut self, body: T) -> Result<Message, EmailError> {
-        let maybe_encoding = self.headers.get::<ContentTransferEncoding>().copied();
+        let maybe_encoding = self.headers.get::<ContentTransferEncoding>();
         let body = body.into_body(maybe_encoding);
 
         self.headers.set(body.encoding());
         self.build(MessageBody::Raw(body.into_vec()))
     }
 
-    /// Create message using mime body ([`MultiPart`][self::MultiPart])
+    /// Create message using mime body ([`MultiPart`])
     pub fn multipart(self, part: MultiPart) -> Result<Message, EmailError> {
         self.mime_1_0().build(MessageBody::Mime(Part::Multi(part)))
     }
 
-    /// Create message using mime body ([`SinglePart`][self::SinglePart])
+    /// Create message using mime body ([`SinglePart`])
     pub fn singlepart(self, part: SinglePart) -> Result<Message, EmailError> {
         self.mime_1_0().build(MessageBody::Mime(Part::Single(part)))
     }
+
+    /// Set `MIME-Version` header to 1.0
+    ///
+    /// Shortcut for `self.header(header::MIME_VERSION_1_0)`.
+    ///
+    /// Not exposed as it is set by body methods
+    fn mime_1_0(self) -> Self {
+        self.header(header::MIME_VERSION_1_0)
+    }
 }
 
 /// Email message which can be formatted
+#[cfg_attr(docsrs, doc(cfg(feature = "builder")))]
 #[derive(Clone, Debug)]
 pub struct Message {
     headers: Headers,
@@ -518,6 +503,11 @@ impl Message {
         &self.headers
     }
 
+    /// Get a mutable reference to the headers
+    pub fn headers_mut(&mut self) -> &mut Headers {
+        &mut self.headers
+    }
+
     /// Get `Message` envelope
     pub fn envelope(&self) -> &Envelope {
         &self.envelope
@@ -529,17 +519,93 @@ impl Message {
         self.format(&mut out);
         out
     }
+
+    #[cfg(feature = "dkim")]
+    /// Format body for signing
+    pub(crate) fn body_raw(&self) -> Vec<u8> {
+        let mut out = Vec::new();
+        match &self.body {
+            MessageBody::Mime(p) => p.format_body(&mut out),
+            MessageBody::Raw(r) => out.extend_from_slice(r),
+        }
+        out.extend_from_slice(b"\r\n");
+        out
+    }
+
+    /// Sign the message using Dkim
+    ///
+    /// Example:
+    /// ```rust
+    /// use lettre::{
+    ///     message::{
+    ///         dkim::{DkimConfig, DkimSigningAlgorithm, DkimSigningKey},
+    ///         header::ContentType,
+    ///     },
+    ///     Message,
+    /// };
+    ///
+    /// let mut message = Message::builder()
+    ///     .from("Alice <alice@example.org>".parse().unwrap())
+    ///     .reply_to("Bob <bob@example.org>".parse().unwrap())
+    ///     .to("Carla <carla@example.net>".parse().unwrap())
+    ///     .subject("Hello")
+    ///     .header(ContentType::TEXT_PLAIN)
+    ///     .body("Hi there, it's a test email, with utf-8 chars ë!\n\n\n".to_owned())
+    ///     .unwrap();
+    /// let key = "-----BEGIN RSA PRIVATE KEY-----
+    /// MIIEowIBAAKCAQEAt2gawjoybf0mAz0mSX0cq1ah5F9cPazZdCwLnFBhRufxaZB8
+    /// NLTdc9xfPIOK8l/xGrN7Nd63J4cTATqZukumczkA46O8YKHwa53pNT6NYwCNtDUL
+    /// eBu+7xUW18GmDzkIFkxGO2R5kkTeWPlKvKpEiicIMfl0OmyW/fI3AbtM7e/gmqQ4
+    /// kEYIO0mTjPT+jTgWE4JIi5KUTHudUBtfMKcSFyM2HkUOExl1c9+A4epjRFQwEXMA
+    /// hM5GrqZoOdUm4fIpvGpLIGIxFgHPpZYbyq6yJZzH3+5aKyCHrsHawPuPiCD45zsU
+    /// re31zCE6b6k1sDiiBR4CaRHnbL7hxFp0aNLOVQIDAQABAoIBAGMK3gBrKxaIcUGo
+    /// gQeIf7XrJ6vK72YC9L8uleqI4a9Hy++E7f4MedZ6eBeWta8jrnEL4Yp6xg+beuDc
+    /// A24+Mhng+6Dyp+TLLqj+8pQlPnbrMprRVms7GIXFrrs+wO1RkBNyhy7FmH0roaMM
+    /// pJZzoGW2pE9QdbqjL3rdlWTi/60xRX9eZ42nNxYnbc+RK03SBd46c3UBha6Y9iQX
+    /// 562yWilDnB5WCX2tBoSN39bEhJvuZDzMwOuGw68Q96Hdz82Iz1xVBnRhH+uNStjR
+    /// VnAssSHVxPSpwWrm3sHlhjBHWPnNIaOKIKl1lbL+qWfVQCj/6a5DquC+vYAeYR6L
+    /// 3mA0z0ECgYEA5YkNYcILSXyE0hZ8eA/t58h8eWvYI5iqt3nT4fznCoYJJ74Vukeg
+    /// 6BTlq/CsanwT1lDtvDKrOaJbA7DPTES/bqT0HoeIdOvAw9w/AZI5DAqYp61i6RMK
+    /// xfAQL/Ik5MDFN8gEMLLXRVMe/aR27f6JFZpShJOK/KCzHqikKfYVJ+UCgYEAzI2F
+    /// ZlTyittWSyUSl5UKyfSnFOx2+6vNy+lu5DeMJu8Wh9rqBk388Bxq98CfkCseWESN
+    /// pTCGdYltz9DvVNBdBLwSMdLuYJAI6U+Zd70MWyuNdHFPyWVHUNqMUBvbUtj2w74q
+    /// Hzu0GI0OrRjdX6C63S17PggmT/N2R9X7P4STxbECgYA+AZAD4I98Ao8+0aQ+Ks9x
+    /// 1c8KXf+9XfiAKAD9A3zGcv72JXtpHwBwsXR5xkJNYcdaFfKi7G0k3J8JmDHnwIqW
+    /// MSlhNeu+6hDg2BaNLhsLDbG/Wi9mFybJ4df9m8Qrp4efUgEPxsAwkgvFKTCXijMu
+    /// CspP1iutoxvAJH50d22voQKBgDIsSFtIXNGYaTs3Va8enK3at5zXP3wNsQXiNRP/
+    /// V/44yNL77EktmewfXFF2yuym1uOZtRCerWxpEClYO0wXa6l8pA3aiiPfUIBByQfo
+    /// s/4s2Z6FKKfikrKPWLlRi+NvWl+65kQQ9eTLvJzSq4IIP61+uWsGvrb/pbSLFPyI
+    /// fWKRAoGBALFCStBXvdMptjq4APUzAdJ0vytZzXkOZHxgmc+R0fQn22OiW0huW6iX
+    /// JcaBbL6ZSBIMA3AdaIjtvNRiomueHqh0GspTgOeCE2585TSFnw6vEOJ8RlR4A0Mw
+    /// I45fbR4l+3D/30WMfZlM6bzZbwPXEnr2s1mirmuQpjumY9wLhK25
+    /// -----END RSA PRIVATE KEY-----";
+    /// let signing_key = DkimSigningKey::new(key, DkimSigningAlgorithm::Rsa).unwrap();
+    /// message.sign(&DkimConfig::default_config(
+    ///     "dkimtest".to_owned(),
+    ///     "example.org".to_owned(),
+    ///     signing_key,
+    /// ));
+    /// println!(
+    ///     "message: {}",
+    ///     std::str::from_utf8(&message.formatted()).unwrap()
+    /// );
+    /// ```
+    #[cfg(feature = "dkim")]
+    pub fn sign(&mut self, dkim_config: &DkimConfig) {
+        dkim_sign(self, dkim_config);
+    }
 }
 
 impl EmailFormat for Message {
     fn format(&self, out: &mut Vec<u8>) {
-        out.extend_from_slice(self.headers.to_string().as_bytes());
+        write!(out, "{}", self.headers)
+            .expect("A Write implementation panicked while formatting headers");
 
         match &self.body {
             MessageBody::Mime(p) => p.format(out),
             MessageBody::Raw(r) => {
                 out.extend_from_slice(b"\r\n");
-                out.extend_from_slice(&r)
+                out.extend_from_slice(r);
             }
         }
     }
@@ -551,9 +617,19 @@ impl Default for MessageBuilder {
     }
 }
 
+/// Create a random message id.
+/// (Not cryptographically random)
+fn make_message_id() -> String {
+    iter::repeat_with(fastrand::alphanumeric).take(36).collect()
+}
+
 #[cfg(test)]
 mod test {
-    use crate::message::{header, mailbox::Mailbox, Message, MultiPart, SinglePart};
+    use std::time::{Duration, SystemTime};
+
+    use pretty_assertions::assert_eq;
+
+    use super::{header, mailbox::Mailbox, make_message_id, Message, MultiPart, SinglePart};
 
     #[test]
     fn email_missing_originator() {
@@ -563,7 +639,7 @@ mod test {
     }
 
     #[test]
-    fn email_miminal_message() {
+    fn email_minimal_message() {
         assert!(Message::builder()
             .from("NoBody <nobody@domain.tld>".parse().unwrap())
             .to("NoBody <nobody@domain.tld>".parse().unwrap())
@@ -581,11 +657,13 @@ mod test {
     }
 
     #[test]
-    fn email_message() {
-        let date = "Tue, 15 Nov 1994 08:12:31 GMT".parse().unwrap();
+    fn email_message_no_bcc() {
+        // Tue, 15 Nov 1994 08:12:31 GMT
+        let date = SystemTime::UNIX_EPOCH + Duration::from_secs(784887151);
 
         let email = Message::builder()
             .date(date)
+            .bcc("hidden@example.com".parse().unwrap())
             .header(header::From(
                 vec![Mailbox::new(
                     Some("Каи".into()),
@@ -596,16 +674,54 @@ mod test {
             .header(header::To(
                 vec!["Pony O.P. <pony@domain.tld>".parse().unwrap()].into(),
             ))
-            .header(header::Subject("яңа ел белән!".into()))
+            .header(header::Subject::from(String::from("яңа ел белән!")))
             .body(String::from("Happy new year!"))
             .unwrap();
 
         assert_eq!(
             String::from_utf8(email.formatted()).unwrap(),
             concat!(
-                "Date: Tue, 15 Nov 1994 08:12:31 GMT\r\n",
+                "Date: Tue, 15 Nov 1994 08:12:31 +0000\r\n",
                 "From: =?utf-8?b?0JrQsNC4?= <kayo@example.com>\r\n",
-                "To: Pony O.P. <pony@domain.tld>\r\n",
+                "To: \"Pony O.P.\" <pony@domain.tld>\r\n",
+                "Subject: =?utf-8?b?0Y/So9CwINC10Lsg0LHQtdC705nQvSE=?=\r\n",
+                "Content-Transfer-Encoding: 7bit\r\n",
+                "\r\n",
+                "Happy new year!"
+            )
+        );
+    }
+
+    #[test]
+    fn email_message_keep_bcc() {
+        // Tue, 15 Nov 1994 08:12:31 GMT
+        let date = SystemTime::UNIX_EPOCH + Duration::from_secs(784887151);
+
+        let email = Message::builder()
+            .date(date)
+            .bcc("hidden@example.com".parse().unwrap())
+            .keep_bcc()
+            .header(header::From(
+                vec![Mailbox::new(
+                    Some("Каи".into()),
+                    "kayo@example.com".parse().unwrap(),
+                )]
+                .into(),
+            ))
+            .header(header::To(
+                vec!["Pony O.P. <pony@domain.tld>".parse().unwrap()].into(),
+            ))
+            .header(header::Subject::from(String::from("яңа ел белән!")))
+            .body(String::from("Happy new year!"))
+            .unwrap();
+
+        assert_eq!(
+            String::from_utf8(email.formatted()).unwrap(),
+            concat!(
+                "Date: Tue, 15 Nov 1994 08:12:31 +0000\r\n",
+                "Bcc: hidden@example.com\r\n",
+                "From: =?utf-8?b?0JrQsNC4?= <kayo@example.com>\r\n",
+                "To: \"Pony O.P.\" <pony@domain.tld>\r\n",
                 "Subject: =?utf-8?b?0Y/So9CwINC10Lsg0LHQtdC705nQvSE=?=\r\n",
                 "Content-Transfer-Encoding: 7bit\r\n",
                 "\r\n",
@@ -616,7 +732,8 @@ mod test {
 
     #[test]
     fn email_with_png() {
-        let date = "Tue, 15 Nov 1994 08:12:31 GMT".parse().unwrap();
+        // Tue, 15 Nov 1994 08:12:31 GMT
+        let date = SystemTime::UNIX_EPOCH + Duration::from_secs(784887151);
         let img = std::fs::read("./docs/lettre.png").unwrap();
         let m = Message::builder()
             .date(date)
@@ -628,21 +745,16 @@ mod test {
                 MultiPart::related()
                     .singlepart(
                         SinglePart::builder()
-                            .header(header::ContentType(
-                                "text/html; charset=utf8".parse().unwrap(),
-                            ))
+                            .header(header::ContentType::TEXT_HTML)
                             .body(String::from(
                                 "<p><b>Hello</b>, <i>world</i>! <img src=cid:123></p>",
                             )),
                     )
                     .singlepart(
                         SinglePart::builder()
-                            .header(header::ContentType("image/png".parse().unwrap()))
-                            .header(header::ContentDisposition {
-                                disposition: header::DispositionType::Inline,
-                                parameters: vec![],
-                            })
-                            .header(header::ContentId("<123>".into()))
+                            .header(header::ContentType::parse("image/png").unwrap())
+                            .header(header::ContentDisposition::inline())
+                            .header(header::ContentId::from(String::from("<123>")))
                             .body(img),
                     ),
             )
@@ -653,11 +765,27 @@ mod test {
         let expected = String::from_utf8(file_expected).unwrap();
 
         for (i, line) in output.lines().zip(expected.lines()).enumerate() {
-            if i == 6 || i == 8 || i == 13 || i == 232 {
+            if i == 7 || i == 9 || i == 14 || i == 233 {
                 continue;
             }
 
-            assert_eq!(line.0, line.1)
+            assert_eq!(line.0, line.1);
+        }
+    }
+
+    #[test]
+    fn test_make_message_id() {
+        let mut ids = std::collections::HashSet::with_capacity(10);
+        for _ in 0..1000 {
+            ids.insert(make_message_id());
+        }
+
+        // Ensure there are no duplicates
+        assert_eq!(1000, ids.len());
+
+        // Ensure correct length
+        for id in ids {
+            assert_eq!(36, id.len());
         }
     }
 }

src/message/utf8_b.rs

@@ -1,60 +0,0 @@
-// https://tools.ietf.org/html/rfc1522
-
-fn allowed_char(c: char) -> bool {
-    c >= 1 as char && c <= 9 as char
-        || c == 11 as char
-        || c == 12 as char
-        || c >= 14 as char && c <= 127 as char
-}
-
-pub fn encode(s: &str) -> String {
-    if s.chars().all(allowed_char) {
-        s.into()
-    } else {
-        format!("=?utf-8?b?{}?=", base64::encode(s))
-    }
-}
-
-pub fn decode(s: &str) -> Option<String> {
-    s.strip_prefix("=?utf-8?b?")
-        .and_then(|stripped| stripped.strip_suffix("?="))
-        .map_or_else(
-            || Some(s.into()),
-            |stripped| {
-                let decoded = base64::decode(stripped).ok()?;
-                let decoded = String::from_utf8(decoded).ok()?;
-                Some(decoded)
-            },
-        )
-}
-
-#[cfg(test)]
-mod test {
-    use super::{decode, encode};
-
-    #[test]
-    fn encode_ascii() {
-        assert_eq!(&encode("Kayo. ?"), "Kayo. ?");
-    }
-
-    #[test]
-    fn decode_ascii() {
-        assert_eq!(decode("Kayo. ?"), Some("Kayo. ?".into()));
-    }
-
-    #[test]
-    fn encode_utf8() {
-        assert_eq!(
-            &encode("Привет, мир!"),
-            "=?utf-8?b?0J/RgNC40LLQtdGCLCDQvNC40YAh?="
-        );
-    }
-
-    #[test]
-    fn decode_utf8() {
-        assert_eq!(
-            decode("=?utf-8?b?0J/RgNC40LLQtdGCLCDQvNC40YAh?="),
-            Some("Привет, мир!".into())
-        );
-    }
-}

src/rustls_crypto.rs

@@ -0,0 +1,14 @@
+use std::sync::Arc;
+
+use rustls::crypto::CryptoProvider;
+
+pub(crate) fn crypto_provider() -> Arc<CryptoProvider> {
+    CryptoProvider::get_default().cloned().unwrap_or_else(|| {
+        #[cfg(feature = "aws-lc-rs")]
+        let provider = rustls::crypto::aws_lc_rs::default_provider();
+        #[cfg(not(feature = "aws-lc-rs"))]
+        let provider = rustls::crypto::ring::default_provider();
+
+        Arc::new(provider)
+    })
+}

src/time.rs

@@ -0,0 +1,26 @@
+use std::time::SystemTime;
+
+#[cfg(feature = "web")]
+pub(crate) fn now() -> SystemTime {
+    fn to_std_systemtime(time: web_time::SystemTime) -> std::time::SystemTime {
+        let duration = time
+            .duration_since(web_time::SystemTime::UNIX_EPOCH)
+            .unwrap();
+        SystemTime::UNIX_EPOCH + duration
+    }
+
+    // FIXME: change to:
+    // #[allow(
+    //     clippy::disallowed_methods,
+    //     reason = "`web-time` aliases `std::time::SystemTime::now` on non-WASM platforms"
+    // )]
+    #[allow(clippy::disallowed_methods)]
+    to_std_systemtime(web_time::SystemTime::now())
+}
+
+#[cfg(not(feature = "web"))]
+pub(crate) fn now() -> SystemTime {
+    // FIXME: change to #[expect(clippy::disallowed_methods, reason = "the `web` feature is disabled")]
+    #[allow(clippy::disallowed_methods)]
+    SystemTime::now()
+}

src/transport/file/error.rs

@@ -1,61 +1,97 @@
 //! Error and result type for file transport
 
-use self::Error::*;
-use std::{
-    error::Error as StdError,
-    fmt::{self, Display, Formatter},
-    io,
-};
+use std::{error::Error as StdError, fmt};
 
-/// An enum of all error kinds.
-#[derive(Debug)]
-pub enum Error {
-    /// Internal client error
-    Client(&'static str),
-    /// IO error
-    Io(io::Error),
-    /// JSON error
-    #[cfg(feature = "file-transport-envelope")]
-    Json(serde_json::Error),
+use crate::BoxError;
+
+/// The Errors that may occur when sending an email over SMTP
+pub struct Error {
+    inner: Box<Inner>,
 }
 
-impl Display for Error {
-    fn fmt(&self, fmt: &mut Formatter<'_>) -> Result<(), fmt::Error> {
-        match *self {
-            Client(err) => fmt.write_str(err),
-            Io(ref err) => err.fmt(fmt),
-            #[cfg(feature = "file-transport-envelope")]
-            Json(ref err) => err.fmt(fmt),
+struct Inner {
+    kind: Kind,
+    source: Option<BoxError>,
+}
+
+impl Error {
+    pub(crate) fn new<E>(kind: Kind, source: Option<E>) -> Error
+    where
+        E: Into<BoxError>,
+    {
+        Error {
+            inner: Box::new(Inner {
+                kind,
+                source: source.map(Into::into),
+            }),
         }
     }
+
+    /// Returns true if the error is a file I/O error
+    pub fn is_io(&self) -> bool {
+        matches!(self.inner.kind, Kind::Io)
+    }
+
+    /// Returns true if the error is an envelope serialization or deserialization error
+    #[cfg(feature = "file-transport-envelope")]
+    pub fn is_envelope(&self) -> bool {
+        matches!(self.inner.kind, Kind::Envelope)
+    }
+}
+
+#[derive(Debug)]
+pub(crate) enum Kind {
+    /// File I/O error
+    Io,
+    /// Envelope serialization/deserialization error
+    #[cfg(feature = "file-transport-envelope")]
+    Envelope,
+}
+
+impl fmt::Debug for Error {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        let mut builder = f.debug_struct("lettre::transport::file::Error");
+
+        builder.field("kind", &self.inner.kind);
+
+        if let Some(source) = &self.inner.source {
+            builder.field("source", source);
+        }
+
+        builder.finish()
+    }
+}
+
+impl fmt::Display for Error {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        match self.inner.kind {
+            Kind::Io => f.write_str("response error")?,
+            #[cfg(feature = "file-transport-envelope")]
+            Kind::Envelope => f.write_str("internal client error")?,
+        }
+
+        if let Some(e) = &self.inner.source {
+            write!(f, ": {e}")?;
+        }
+
+        Ok(())
+    }
 }
 
 impl StdError for Error {
     fn source(&self) -> Option<&(dyn StdError + 'static)> {
-        match *self {
-            Io(ref err) => Some(&*err),
-            #[cfg(feature = "file-transport-envelope")]
-            Json(ref err) => Some(&*err),
-            _ => None,
-        }
+        self.inner.source.as_ref().map(|e| {
+            let r: &(dyn std::error::Error + 'static) = &**e;
+            r
+        })
     }
 }
 
-impl From<io::Error> for Error {
-    fn from(err: io::Error) -> Error {
-        Error::Io(err)
-    }
+pub(crate) fn io<E: Into<BoxError>>(e: E) -> Error {
+    Error::new(Kind::Io, Some(e))
 }
 
 #[cfg(feature = "file-transport-envelope")]
-impl From<serde_json::Error> for Error {
-    fn from(err: serde_json::Error) -> Error {
-        Error::Json(err)
-    }
-}
-
-impl From<&'static str> for Error {
-    fn from(string: &'static str) -> Error {
-        Error::Client(string)
-    }
+pub(crate) fn envelope<E: Into<BoxError>>(e: E) -> Error {
+    Error::new(Kind::Envelope, Some(e))
 }

src/transport/file/mod.rs

@@ -6,11 +6,12 @@
 //!
 //! ```rust
 //! # use std::error::Error;
-//!
+//! #
 //! # #[cfg(all(feature = "file-transport", feature = "builder"))]
 //! # fn main() -> Result<(), Box<dyn Error>> {
 //! use std::env::temp_dir;
-//! use lettre::{Transport, Message, FileTransport};
+//!
+//! use lettre::{message::header::ContentType, FileTransport, Message, Transport};
 //!
 //! // Write to the local temp directory
 //! let sender = FileTransport::new(temp_dir());
@@ -19,10 +20,10 @@
 //!     .reply_to("Yuin <yuin@domain.tld>".parse()?)
 //!     .to("Hei <hei@domain.tld>".parse()?)
 //!     .subject("Happy new year")
+//!     .header(ContentType::TEXT_PLAIN)
 //!     .body(String::from("Be happy!"))?;
 //!
-//! let result = sender.send(&email);
-//! assert!(result.is_ok());
+//! sender.send(&email)?;
 //! # Ok(())
 //! # }
 //!
@@ -38,11 +39,12 @@
 //!
 //! ```rust
 //! # use std::error::Error;
-//!
+//! #
 //! # #[cfg(all(feature = "file-transport-envelope", feature = "builder"))]
 //! # fn main() -> Result<(), Box<dyn Error>> {
 //! use std::env::temp_dir;
-//! use lettre::{Transport, Message, FileTransport};
+//!
+//! use lettre::{message::header::ContentType, FileTransport, Message, Transport};
 //!
 //! // Write to the local temp directory
 //! let sender = FileTransport::with_envelope(temp_dir());
@@ -51,10 +53,10 @@
 //!     .reply_to("Yuin <yuin@domain.tld>".parse()?)
 //!     .to("Hei <hei@domain.tld>".parse()?)
 //!     .subject("Happy new year")
+//!     .header(ContentType::TEXT_PLAIN)
 //!     .body(String::from("Be happy!"))?;
 //!
-//! let result = sender.send(&email);
-//! assert!(result.is_ok());
+//! sender.send(&email)?;
 //! # Ok(())
 //! # }
 //!
@@ -66,23 +68,26 @@
 //!
 //! ```rust,no_run
 //! # use std::error::Error;
-//!
+//! #
 //! # #[cfg(all(feature = "tokio1", feature = "file-transport", feature = "builder"))]
 //! # async fn run() -> Result<(), Box<dyn Error>> {
 //! use std::env::temp_dir;
-//! use lettre::{Tokio1Transport, Message, FileTransport};
+//!
+//! use lettre::{
+//!     message::header::ContentType, AsyncFileTransport, AsyncTransport, Message, Tokio1Executor,
+//! };
 //!
 //! // Write to the local temp directory
-//! let sender = FileTransport::new(temp_dir());
+//! let sender = AsyncFileTransport::<Tokio1Executor>::new(temp_dir());
 //! let email = Message::builder()
 //!     .from("NoBody <nobody@domain.tld>".parse()?)
 //!     .reply_to("Yuin <yuin@domain.tld>".parse()?)
 //!     .to("Hei <hei@domain.tld>".parse()?)
 //!     .subject("Happy new year")
+//!     .header(ContentType::TEXT_PLAIN)
 //!     .body(String::from("Be happy!"))?;
 //!
-//! let result = sender.send(email).await;
-//! assert!(result.is_ok());
+//! sender.send(email).await?;
 //! # Ok(())
 //! # }
 //! ```
@@ -91,23 +96,27 @@
 //!
 //! ```rust,no_run
 //! # use std::error::Error;
-//!
+//! #
 //! # #[cfg(all(feature = "async-std1", feature = "file-transport", feature = "builder"))]
 //! # async fn run() -> Result<(), Box<dyn Error>> {
 //! use std::env::temp_dir;
-//! use lettre::{AsyncStd1Transport, Message, FileTransport};
+//!
+//! use lettre::{
+//!     message::header::ContentType, AsyncFileTransport, AsyncStd1Executor, AsyncTransport,
+//!     Message,
+//! };
 //!
 //! // Write to the local temp directory
-//! let sender = FileTransport::new(temp_dir());
+//! let sender = AsyncFileTransport::<AsyncStd1Executor>::new(temp_dir());
 //! let email = Message::builder()
 //!     .from("NoBody <nobody@domain.tld>".parse()?)
 //!     .reply_to("Yuin <yuin@domain.tld>".parse()?)
 //!     .to("Hei <hei@domain.tld>".parse()?)
 //!     .subject("Happy new year")
+//!     .header(ContentType::TEXT_PLAIN)
 //!     .body(String::from("Be happy!"))?;
 //!
-//! let result = sender.send(email).await;
-//! assert!(result.is_ok());
+//! sender.send(email).await?;
 //! # Ok(())
 //! # }
 //! ```
@@ -121,6 +130,7 @@
 //! Reply-To: Yuin <yuin@domain.tld>
 //! To: Hei <hei@domain.tld>
 //! Subject: Happy new year
+//! Content-Type: text/plain; charset=utf-8
 //! Date: Tue, 18 Aug 2020 22:50:17 GMT
 //!
 //! Be happy!
@@ -132,36 +142,46 @@
 //! {"forward_path":["hei@domain.tld"],"reverse_path":"nobody@domain.tld"}
 //! ```
 
-pub use self::error::Error;
-use crate::address::Envelope;
-#[cfg(feature = "async-std1")]
-use crate::AsyncStd1Transport;
-#[cfg(feature = "tokio02")]
-use crate::Tokio02Transport;
-#[cfg(feature = "tokio1")]
-use crate::Tokio1Transport;
-use crate::Transport;
-#[cfg(any(feature = "async-std1", feature = "tokio02", feature = "tokio1"))]
-use async_trait::async_trait;
+#[cfg(any(feature = "async-std1", feature = "tokio1"))]
+use std::marker::PhantomData;
 use std::{
     path::{Path, PathBuf},
     str,
 };
+
+#[cfg(any(feature = "async-std1", feature = "tokio1"))]
+use async_trait::async_trait;
 use uuid::Uuid;
 
+pub use self::error::Error;
+use crate::{address::Envelope, Transport};
+#[cfg(any(feature = "async-std1", feature = "tokio1"))]
+use crate::{AsyncTransport, Executor};
+
 mod error;
 
 type Id = String;
 
 /// Writes the content and the envelope information to a file
-#[derive(Debug)]
+#[derive(Debug, Clone)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
+#[cfg_attr(docsrs, doc(cfg(feature = "file-transport")))]
 pub struct FileTransport {
     path: PathBuf,
     #[cfg(feature = "file-transport-envelope")]
     save_envelope: bool,
 }
 
+/// Asynchronously writes the content and the envelope information to a file
+#[derive(Debug, Clone)]
+#[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
+#[cfg_attr(docsrs, doc(cfg(any(feature = "tokio1", feature = "async-std1"))))]
+#[cfg(any(feature = "async-std1", feature = "tokio1"))]
+pub struct AsyncFileTransport<E: Executor> {
+    inner: FileTransport,
+    marker_: PhantomData<E>,
+}
+
 impl FileTransport {
     /// Creates a new transport to the given directory
     ///
@@ -187,8 +207,68 @@ impl FileTransport {
         }
     }
 
+    /// Read a message that was written using the file transport.
+    ///
+    /// Reads the envelope and the raw message content.
+    #[cfg(feature = "file-transport-envelope")]
+    pub fn read(&self, email_id: &str) -> Result<(Envelope, Vec<u8>), Error> {
+        use std::fs;
+
+        let eml_file = self.path.join(format!("{email_id}.eml"));
+        let eml = fs::read(eml_file).map_err(error::io)?;
+
+        let json_file = self.path.join(format!("{email_id}.json"));
+        let json = fs::read(json_file).map_err(error::io)?;
+        let envelope = serde_json::from_slice(&json).map_err(error::envelope)?;
+
+        Ok((envelope, eml))
+    }
+
     fn path(&self, email_id: &Uuid, extension: &str) -> PathBuf {
-        self.path.join(format!("{}.{}", email_id, extension))
+        self.path.join(format!("{email_id}.{extension}"))
+    }
+}
+
+#[cfg(any(feature = "async-std1", feature = "tokio1"))]
+impl<E> AsyncFileTransport<E>
+where
+    E: Executor,
+{
+    /// Creates a new transport to the given directory
+    ///
+    /// Writes the email content in eml format.
+    pub fn new<P: AsRef<Path>>(path: P) -> Self {
+        Self {
+            inner: FileTransport::new(path),
+            marker_: PhantomData,
+        }
+    }
+
+    /// Creates a new transport to the given directory
+    ///
+    /// Writes the email content in eml format and the envelope
+    /// in json format.
+    #[cfg(feature = "file-transport-envelope")]
+    pub fn with_envelope<P: AsRef<Path>>(path: P) -> Self {
+        Self {
+            inner: FileTransport::with_envelope(path),
+            marker_: PhantomData,
+        }
+    }
+
+    /// Read a message that was written using the file transport.
+    ///
+    /// Reads the envelope and the raw message content.
+    #[cfg(feature = "file-transport-envelope")]
+    pub async fn read(&self, email_id: &str) -> Result<(Envelope, Vec<u8>), Error> {
+        let eml_file = self.inner.path.join(format!("{email_id}.eml"));
+        let eml = E::fs_read(&eml_file).await.map_err(error::io)?;
+
+        let json_file = self.inner.path.join(format!("{email_id}.json"));
+        let json = E::fs_read(&json_file).await.map_err(error::io)?;
+        let envelope = serde_json::from_slice(&json).map_err(error::envelope)?;
+
+        Ok((envelope, eml))
     }
 }
 
@@ -202,13 +282,16 @@ impl Transport for FileTransport {
         let email_id = Uuid::new_v4();
 
         let file = self.path(&email_id, "eml");
-        fs::write(file, email)?;
+        #[cfg(feature = "tracing")]
+        tracing::debug!(?file, "writing email to");
+        fs::write(file, email).map_err(error::io)?;
 
         #[cfg(feature = "file-transport-envelope")]
         {
             if self.save_envelope {
                 let file = self.path(&email_id, "json");
-                fs::write(file, serde_json::to_string(&envelope)?)?;
+                let buf = serde_json::to_string(&envelope).map_err(error::envelope)?;
+                fs::write(file, buf).map_err(error::io)?;
             }
         }
         // use envelope anyway
@@ -218,80 +301,29 @@ impl Transport for FileTransport {
     }
 }
 
-#[cfg(feature = "async-std1")]
+#[cfg(any(feature = "async-std1", feature = "tokio1"))]
 #[async_trait]
-impl AsyncStd1Transport for FileTransport {
+impl<E> AsyncTransport for AsyncFileTransport<E>
+where
+    E: Executor,
+{
     type Ok = Id;
     type Error = Error;
 
     async fn send_raw(&self, envelope: &Envelope, email: &[u8]) -> Result<Self::Ok, Self::Error> {
-        use async_std::fs;
-
         let email_id = Uuid::new_v4();
 
-        let file = self.path(&email_id, "eml");
-        fs::write(file, email).await?;
+        let file = self.inner.path(&email_id, "eml");
+        #[cfg(feature = "tracing")]
+        tracing::debug!(?file, "writing email to");
+        E::fs_write(&file, email).await.map_err(error::io)?;
 
         #[cfg(feature = "file-transport-envelope")]
         {
-            if self.save_envelope {
-                let file = self.path(&email_id, "json");
-                fs::write(file, serde_json::to_string(&envelope)?).await?;
-            }
-        }
-        // use envelope anyway
-        let _ = envelope;
-
-        Ok(email_id.to_string())
-    }
-}
-
-#[cfg(feature = "tokio02")]
-#[async_trait]
-impl Tokio02Transport for FileTransport {
-    type Ok = Id;
-    type Error = Error;
-
-    async fn send_raw(&self, envelope: &Envelope, email: &[u8]) -> Result<Self::Ok, Self::Error> {
-        use tokio02_crate::fs;
-
-        let email_id = Uuid::new_v4();
-        let file = self.path(&email_id, "eml");
-        fs::write(file, email).await?;
-
-        #[cfg(feature = "file-transport-envelope")]
-        {
-            if self.save_envelope {
-                let file = self.path(&email_id, "json");
-                fs::write(file, serde_json::to_string(&envelope)?).await?;
-            }
-        }
-        // use envelope anyway
-        let _ = envelope;
-
-        Ok(email_id.to_string())
-    }
-}
-
-#[cfg(feature = "tokio1")]
-#[async_trait]
-impl Tokio1Transport for FileTransport {
-    type Ok = Id;
-    type Error = Error;
-
-    async fn send_raw(&self, envelope: &Envelope, email: &[u8]) -> Result<Self::Ok, Self::Error> {
-        use tokio1_crate::fs;
-
-        let email_id = Uuid::new_v4();
-
-        let file = self.path(&email_id, "eml");
-        fs::write(file, email).await?;
-
-        #[cfg(feature = "file-transport-envelope")]
-        {
-            if self.save_envelope {
-                let file = self.path(&email_id, "json");
-                fs::write(file, serde_json::to_string(&envelope)?).await?;
+            if self.inner.save_envelope {
+                let file = self.inner.path(&email_id, "json");
+                let buf = serde_json::to_vec(&envelope).map_err(error::envelope)?;
+                E::fs_write(&file, &buf).await.map_err(error::io)?;
             }
         }
         // use envelope anyway

src/transport/mod.rs

@@ -1,20 +1,114 @@
-//! ### Sending Messages
+//! ## Transports for sending emails
 //!
-//! This section explains how to manipulate emails you have created.
+//! This module contains `Transport`s for sending emails. A `Transport` implements a high-level API
+//! for sending emails. It automatically manages the underlying resources and doesn't require any
+//! specific knowledge of email protocols in order to be used.
 //!
-//! This mailer contains several different transports for your emails. To be sendable, the
-//! emails have to implement `Email`, which is the case for emails created with `lettre::builder`.
+//! ### Getting started
+//!
+//! Sending emails from your programs requires using an email relay, as client libraries are not
+//! designed to handle email delivery by themselves. Depending on your infrastructure, your relay
+//! could be:
+//!
+//! * a service from your Cloud or hosting provider
+//! * an email server ([MTA] for Mail Transfer Agent, like Postfix or Exchange), running either
+//!   locally on your servers or accessible over the network
+//! * a dedicated external service, like Mailchimp, Mailgun, etc.
+//!
+//! In most cases, the best option is to:
+//!
+//! * Use the [`SMTP`] transport, with the [`relay`] builder (or one of its async counterparts)
+//!   with your server's hostname. They provide modern and secure defaults.
+//! * Use the [`credentials`] method of the builder to pass your credentials.
+//!
+//! These should be enough to safely cover most use cases.
+//!
+//! ### Available transports
 //!
 //! The following transports are available:
 //!
-//! * The `SmtpTransport` uses the SMTP protocol to send the message over the network. It is
-//!   the preferred way of sending emails.
-//! * The `SendmailTransport` uses the sendmail command to send messages. It is an alternative to
-//!   the SMTP transport.
-//! * The `FileTransport` creates a file containing the email content to be sent. It can be used
-//!   for debugging or if you want to keep all sent emails.
-//! * The `StubTransport` is useful for debugging, and only prints the content of the email in the
-//!   logs.
+//! | Module       | Protocol | Sync API              | Async API                  | Description                                             |
+//! | ------------ | -------- | --------------------- | -------------------------- | ------------------------------------------------------- |
+//! | [`smtp`]     | SMTP     | [`SmtpTransport`]     | [`AsyncSmtpTransport`]     | Uses the SMTP protocol to send emails to a relay server |
+//! | [`sendmail`] | Sendmail | [`SendmailTransport`] | [`AsyncSendmailTransport`] | Uses the `sendmail` command to send emails              |
+//! | [`file`]     | File     | [`FileTransport`]     | [`AsyncFileTransport`]     | Saves the email as an `.eml` file                       |
+//! | [`stub`]     | Debug    | [`StubTransport`]     | [`AsyncStubTransport`]     | Drops the email - Useful for debugging                  |
+//!
+//! ## Building an email
+//!
+//! Emails can either be built though [`Message`], which is a typed API for constructing emails
+//! (find out more about it by going over the [`message`][crate::message] module),
+//! or via external means.
+//!
+//! [`Message`]s can be sent via [`Transport::send`] or [`AsyncTransport::send`], while messages
+//! built without lettre's [`message`][crate::message] APIs can be sent via [`Transport::send_raw`]
+//! or [`AsyncTransport::send_raw`].
+//!
+//! ## Brief example
+//!
+//! This example shows how to build an email and send it via an SMTP relay server.
+//! It is in no way a complete example, but it shows how to get started with lettre.
+//! More examples can be found by looking at the specific modules, linked in the _Module_ column
+//! of the [table above](#transports-for-sending-emails).
+//!
+//! ```rust,no_run
+//! # use std::error::Error;
+//! #
+//! # #[cfg(all(feature = "builder", feature = "smtp-transport"))]
+//! # fn main() -> Result<(), Box<dyn Error>> {
+//! use lettre::{
+//!     message::header::ContentType, transport::smtp::authentication::Credentials, Message,
+//!     SmtpTransport, Transport,
+//! };
+//!
+//! let email = Message::builder()
+//!     .from("NoBody <nobody@domain.tld>".parse()?)
+//!     .reply_to("Yuin <yuin@domain.tld>".parse()?)
+//!     .to("Hei <hei@domain.tld>".parse()?)
+//!     .subject("Happy new year")
+//!     .header(ContentType::TEXT_PLAIN)
+//!     .body(String::from("Be happy!"))?;
+//!
+//! let creds = Credentials::new("smtp_username".to_owned(), "smtp_password".to_owned());
+//!
+//! // Open a remote connection to the SMTP relay server
+//! let mailer = SmtpTransport::relay("smtp.gmail.com")?
+//!     .credentials(creds)
+//!     .build();
+//!
+//! // Send the email
+//! match mailer.send(&email) {
+//!     Ok(_) => println!("Email sent successfully!"),
+//!     Err(e) => panic!("Could not send email: {e:?}"),
+//! }
+//! # Ok(())
+//! # }
+//! # #[cfg(not(all(feature = "builder", feature = "smtp-transport")))]
+//! # fn main() {}
+//! ```
+//!
+//! [MTA]: https://en.wikipedia.org/wiki/Message_transfer_agent
+//! [`SMTP`]: crate::transport::smtp
+//! [`relay`]: crate::SmtpTransport::relay
+//! [`starttls_relay`]: crate::SmtpTransport::starttls_relay
+//! [`credentials`]: crate::transport::smtp::SmtpTransportBuilder::credentials
+//! [`Message`]: crate::Message
+//! [`file`]: self::file
+//! [`SmtpTransport`]: crate::SmtpTransport
+//! [`AsyncSmtpTransport`]: crate::AsyncSmtpTransport
+//! [`SendmailTransport`]: crate::SendmailTransport
+//! [`AsyncSendmailTransport`]: crate::AsyncSendmailTransport
+//! [`FileTransport`]: crate::FileTransport
+//! [`AsyncFileTransport`]: crate::AsyncFileTransport
+//! [`StubTransport`]: crate::transport::stub::StubTransport
+//! [`AsyncStubTransport`]: crate::transport::stub::AsyncStubTransport
+
+#[cfg(any(feature = "async-std1", feature = "tokio1"))]
+use async_trait::async_trait;
+
+use crate::Envelope;
+#[cfg(feature = "builder")]
+use crate::Message;
 
 #[cfg(feature = "file-transport")]
 #[cfg_attr(docsrs, doc(cfg(feature = "file-transport")))]
@@ -26,3 +120,58 @@ pub mod sendmail;
 #[cfg_attr(docsrs, doc(cfg(feature = "smtp-transport")))]
 pub mod smtp;
 pub mod stub;
+
+/// Blocking Transport method for emails
+pub trait Transport {
+    /// Response produced by the Transport
+    type Ok;
+    /// Error produced by the Transport
+    type Error;
+
+    /// Sends the email
+    #[cfg(feature = "builder")]
+    #[cfg_attr(docsrs, doc(cfg(feature = "builder")))]
+    fn send(&self, message: &Message) -> Result<Self::Ok, Self::Error> {
+        #[cfg(feature = "tracing")]
+        tracing::trace!("starting to send an email");
+
+        let raw = message.formatted();
+        self.send_raw(message.envelope(), &raw)
+    }
+
+    fn send_raw(&self, envelope: &Envelope, email: &[u8]) -> Result<Self::Ok, Self::Error>;
+
+    /// Shuts down the transport. Future calls to [`Self::send`] and
+    /// [`Self::send_raw`] might fail.
+    fn shutdown(&self) {}
+}
+
+/// Async Transport method for emails
+#[cfg(any(feature = "tokio1", feature = "async-std1"))]
+#[cfg_attr(docsrs, doc(cfg(any(feature = "tokio1", feature = "async-std1"))))]
+#[async_trait]
+pub trait AsyncTransport {
+    /// Response produced by the Transport
+    type Ok;
+    /// Error produced by the Transport
+    type Error;
+
+    /// Sends the email
+    #[cfg(feature = "builder")]
+    #[cfg_attr(docsrs, doc(cfg(feature = "builder")))]
+    // TODO take &Message
+    async fn send(&self, message: Message) -> Result<Self::Ok, Self::Error> {
+        #[cfg(feature = "tracing")]
+        tracing::trace!("starting to send an email");
+
+        let raw = message.formatted();
+        let envelope = message.envelope();
+        self.send_raw(envelope, &raw).await
+    }
+
+    async fn send_raw(&self, envelope: &Envelope, email: &[u8]) -> Result<Self::Ok, Self::Error>;
+
+    /// Shuts down the transport. Future calls to [`Self::send`] and
+    /// [`Self::send_raw`] might fail.
+    async fn shutdown(&self) {}
+}

src/transport/sendmail/error.rs

@@ -1,52 +1,93 @@
 //! Error and result type for sendmail transport
 
-use self::Error::*;
-use std::{
-    error::Error as StdError,
-    fmt::{self, Display, Formatter},
-    io,
-    string::FromUtf8Error,
-};
+use std::{error::Error as StdError, fmt};
 
-/// An enum of all error kinds.
-#[derive(Debug)]
-pub enum Error {
-    /// Internal client error
-    Client(String),
-    /// Error parsing UTF8 in response
-    Utf8Parsing(FromUtf8Error),
-    /// IO error
-    Io(io::Error),
+use crate::BoxError;
+
+/// The Errors that may occur when sending an email over sendmail
+pub struct Error {
+    inner: Box<Inner>,
 }
 
-impl Display for Error {
-    fn fmt(&self, fmt: &mut Formatter<'_>) -> Result<(), fmt::Error> {
-        match *self {
-            Client(ref err) => err.fmt(fmt),
-            Utf8Parsing(ref err) => err.fmt(fmt),
-            Io(ref err) => err.fmt(fmt),
+struct Inner {
+    kind: Kind,
+    source: Option<BoxError>,
+}
+
+impl Error {
+    pub(crate) fn new<E>(kind: Kind, source: Option<E>) -> Error
+    where
+        E: Into<BoxError>,
+    {
+        Error {
+            inner: Box::new(Inner {
+                kind,
+                source: source.map(Into::into),
+            }),
         }
     }
+
+    /// Returns true if the error is from client
+    pub fn is_client(&self) -> bool {
+        matches!(self.inner.kind, Kind::Client)
+    }
+
+    /// Returns true if the error comes from the response
+    pub fn is_response(&self) -> bool {
+        matches!(self.inner.kind, Kind::Response)
+    }
+}
+
+#[derive(Debug)]
+pub(crate) enum Kind {
+    /// Error parsing a response
+    Response,
+    /// Internal client error
+    Client,
+}
+
+impl fmt::Debug for Error {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        let mut builder = f.debug_struct("lettre::transport::sendmail::Error");
+
+        builder.field("kind", &self.inner.kind);
+
+        if let Some(source) = &self.inner.source {
+            builder.field("source", source);
+        }
+
+        builder.finish()
+    }
+}
+
+impl fmt::Display for Error {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        match self.inner.kind {
+            Kind::Response => f.write_str("response error")?,
+            Kind::Client => f.write_str("internal client error")?,
+        }
+
+        if let Some(e) = &self.inner.source {
+            write!(f, ": {e}")?;
+        }
+
+        Ok(())
+    }
 }
 
 impl StdError for Error {
     fn source(&self) -> Option<&(dyn StdError + 'static)> {
-        match *self {
-            Io(ref err) => Some(&*err),
-            Utf8Parsing(ref err) => Some(&*err),
-            _ => None,
-        }
+        self.inner.source.as_ref().map(|e| {
+            let r: &(dyn std::error::Error + 'static) = &**e;
+            r
+        })
     }
 }
 
-impl From<io::Error> for Error {
-    fn from(err: io::Error) -> Error {
-        Error::Io(err)
-    }
+pub(crate) fn response<E: Into<BoxError>>(e: E) -> Error {
+    Error::new(Kind::Response, Some(e))
 }
 
-impl From<FromUtf8Error> for Error {
-    fn from(err: FromUtf8Error) -> Error {
-        Utf8Parsing(err)
-    }
+pub(crate) fn client<E: Into<BoxError>>(e: E) -> Error {
+    Error::new(Kind::Client, Some(e))
 }

src/transport/sendmail/mod.rs

@@ -1,24 +1,24 @@
-//! The sendmail transport sends the email using the local sendmail command.
+//! The sendmail transport sends the email using the local `sendmail` command.
 //!
 //! ## Sync example
 //!
 //! ```rust
 //! # use std::error::Error;
-//!
+//! #
 //! # #[cfg(all(feature = "sendmail-transport", feature = "builder"))]
 //! # fn main() -> Result<(), Box<dyn Error>> {
-//! # use lettre::{Message, Transport, SendmailTransport};
+//! use lettre::{message::header::ContentType, Message, SendmailTransport, Transport};
 //!
 //! let email = Message::builder()
 //!     .from("NoBody <nobody@domain.tld>".parse()?)
 //!     .reply_to("Yuin <yuin@domain.tld>".parse()?)
 //!     .to("Hei <hei@domain.tld>".parse()?)
 //!     .subject("Happy new year")
+//!     .header(ContentType::TEXT_PLAIN)
 //!     .body(String::from("Be happy!"))?;
 //!
 //! let sender = SendmailTransport::new();
-//! let result = sender.send(&email);
-//! assert!(result.is_ok());
+//! sender.send(&email)?;
 //! # Ok(())
 //! # }
 //!
@@ -26,48 +26,28 @@
 //! # fn main() {}
 //! ```
 //!
-//! ## Async tokio 0.2 example
-//!
-//! ```rust,no_run
-//! # use std::error::Error;
-//!
-//! # #[cfg(all(feature = "tokio02", feature = "sendmail-transport", feature = "builder"))]
-//! # async fn run() -> Result<(), Box<dyn Error>> {
-//! use lettre::{Message, Tokio02Transport, SendmailTransport};
-//!
-//! let email = Message::builder()
-//!     .from("NoBody <nobody@domain.tld>".parse()?)
-//!     .reply_to("Yuin <yuin@domain.tld>".parse()?)
-//!     .to("Hei <hei@domain.tld>".parse()?)
-//!     .subject("Happy new year")
-//!     .body(String::from("Be happy!"))?;
-//!
-//! let sender = SendmailTransport::new();
-//! let result = sender.send(email).await;
-//! assert!(result.is_ok());
-//! # Ok(())
-//! # }
-//! ```
-//!
 //! ## Async tokio 1.x example
 //!
 //! ```rust,no_run
 //! # use std::error::Error;
-//!
+//! #
 //! # #[cfg(all(feature = "tokio1", feature = "sendmail-transport", feature = "builder"))]
 //! # async fn run() -> Result<(), Box<dyn Error>> {
-//! use lettre::{Message, Tokio1Transport, SendmailTransport};
+//! use lettre::{
+//!     message::header::ContentType, AsyncSendmailTransport, AsyncTransport, Message,
+//!     SendmailTransport, Tokio1Executor,
+//! };
 //!
 //! let email = Message::builder()
 //!     .from("NoBody <nobody@domain.tld>".parse()?)
 //!     .reply_to("Yuin <yuin@domain.tld>".parse()?)
 //!     .to("Hei <hei@domain.tld>".parse()?)
 //!     .subject("Happy new year")
+//!     .header(ContentType::TEXT_PLAIN)
 //!     .body(String::from("Be happy!"))?;
 //!
-//! let sender = SendmailTransport::new();
-//! let result = sender.send(email).await;
-//! assert!(result.is_ok());
+//! let sender = AsyncSendmailTransport::<Tokio1Executor>::new();
+//! sender.send(email).await?;
 //! # Ok(())
 //! # }
 //! ```
@@ -76,58 +56,74 @@
 //!
 //!```rust,no_run
 //! # use std::error::Error;
-//!
+//! #
 //! # #[cfg(all(feature = "async-std1", feature = "sendmail-transport", feature = "builder"))]
 //! # async fn run() -> Result<(), Box<dyn Error>> {
-//! use lettre::{Message, AsyncStd1Transport, SendmailTransport};
+//! use lettre::{Message, AsyncTransport, AsyncStd1Executor,message::header::ContentType, AsyncSendmailTransport};
 //!
 //! let email = Message::builder()
 //!     .from("NoBody <nobody@domain.tld>".parse()?)
 //!     .reply_to("Yuin <yuin@domain.tld>".parse()?)
 //!     .to("Hei <hei@domain.tld>".parse()?)
-//!     .subject("Happy new year")
+//!     .subject("Happy new year").header(ContentType::TEXT_PLAIN)
 //!     .body(String::from("Be happy!"))?;
 //!
-//! let sender = SendmailTransport::new();
-//! let result = sender.send(email).await;
-//! assert!(result.is_ok());
+//! let sender = AsyncSendmailTransport::<AsyncStd1Executor>::new();
+//! sender.send(email).await?;
 //! # Ok(())
 //! # }
 //! ```
 
-pub use self::error::Error;
-use crate::address::Envelope;
-#[cfg(feature = "async-std1")]
-use crate::AsyncStd1Transport;
-#[cfg(feature = "tokio02")]
-use crate::Tokio02Transport;
-#[cfg(feature = "tokio1")]
-use crate::Tokio1Transport;
-use crate::Transport;
-#[cfg(any(feature = "async-std1", feature = "tokio02", feature = "tokio1"))]
-use async_trait::async_trait;
+#[cfg(any(feature = "async-std1", feature = "tokio1"))]
+use std::marker::PhantomData;
 use std::{
     ffi::OsString,
-    io::prelude::*,
+    io::Write,
     process::{Command, Stdio},
 };
 
+#[cfg(any(feature = "async-std1", feature = "tokio1"))]
+use async_trait::async_trait;
+
+pub use self::error::Error;
+#[cfg(feature = "async-std1")]
+use crate::AsyncStd1Executor;
+#[cfg(feature = "tokio1")]
+use crate::Tokio1Executor;
+use crate::{address::Envelope, Transport};
+#[cfg(any(feature = "async-std1", feature = "tokio1"))]
+use crate::{AsyncTransport, Executor};
+
 mod error;
 
-const DEFAUT_SENDMAIL: &str = "/usr/sbin/sendmail";
+const DEFAULT_SENDMAIL: &str = "sendmail";
 
-/// Sends an email using the `sendmail` command
+/// Sends emails using the `sendmail` command
 #[derive(Debug, Clone)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
+#[cfg_attr(docsrs, doc(cfg(feature = "sendmail-transport")))]
 pub struct SendmailTransport {
     command: OsString,
 }
 
+/// Asynchronously sends emails using the `sendmail` command
+#[derive(Debug, Clone)]
+#[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
+#[cfg(any(feature = "async-std1", feature = "tokio1"))]
+#[cfg_attr(docsrs, doc(cfg(any(feature = "tokio1", feature = "async-std1"))))]
+pub struct AsyncSendmailTransport<E: Executor> {
+    inner: SendmailTransport,
+    marker_: PhantomData<E>,
+}
+
 impl SendmailTransport {
-    /// Creates a new transport with the default `/usr/sbin/sendmail` command
+    /// Creates a new transport with the `sendmail` command
+    ///
+    /// Note: This uses the `sendmail` command in the current `PATH`. To use another command,
+    /// use [`SendmailTransport::new_with_command`].
     pub fn new() -> SendmailTransport {
         SendmailTransport {
-            command: DEFAUT_SENDMAIL.into(),
+            command: DEFAULT_SENDMAIL.into(),
         }
     }
 
@@ -151,30 +147,37 @@ impl SendmailTransport {
             .stderr(Stdio::piped());
         c
     }
+}
 
-    #[cfg(feature = "tokio02")]
-    fn tokio02_command(&self, envelope: &Envelope) -> tokio02_crate::process::Command {
-        use tokio02_crate::process::Command;
-
-        let mut c = Command::new(&self.command);
-        c.kill_on_drop(true);
-        c.arg("-i");
-        if let Some(from) = envelope.from() {
-            c.arg("-f").arg(from);
+#[cfg(any(feature = "async-std1", feature = "tokio1"))]
+impl<E> AsyncSendmailTransport<E>
+where
+    E: Executor,
+{
+    /// Creates a new transport with the `sendmail` command
+    ///
+    /// Note: This uses the `sendmail` command in the current `PATH`. To use another command,
+    /// use [`AsyncSendmailTransport::new_with_command`].
+    pub fn new() -> Self {
+        Self {
+            inner: SendmailTransport::new(),
+            marker_: PhantomData,
+        }
+    }
+
+    /// Creates a new transport to the given sendmail command
+    pub fn new_with_command<S: Into<OsString>>(command: S) -> Self {
+        Self {
+            inner: SendmailTransport::new_with_command(command),
+            marker_: PhantomData,
         }
-        c.arg("--")
-            .args(envelope.to())
-            .stdin(Stdio::piped())
-            .stdout(Stdio::piped())
-            .stderr(Stdio::piped());
-        c
     }
 
     #[cfg(feature = "tokio1")]
     fn tokio1_command(&self, envelope: &Envelope) -> tokio1_crate::process::Command {
         use tokio1_crate::process::Command;
 
-        let mut c = Command::new(&self.command);
+        let mut c = Command::new(&self.inner.command);
         c.kill_on_drop(true);
         c.arg("-i");
         if let Some(from) = envelope.from() {
@@ -192,7 +195,7 @@ impl SendmailTransport {
     fn async_std_command(&self, envelope: &Envelope) -> async_std::process::Command {
         use async_std::process::Command;
 
-        let mut c = Command::new(&self.command);
+        let mut c = Command::new(&self.inner.command);
         // TODO: figure out why enabling this kills it earlier
         // c.kill_on_drop(true);
         c.arg("-i");
@@ -214,96 +217,110 @@ impl Default for SendmailTransport {
     }
 }
 
+#[cfg(any(feature = "async-std1", feature = "tokio1"))]
+impl<E> Default for AsyncSendmailTransport<E>
+where
+    E: Executor,
+{
+    fn default() -> Self {
+        Self::new()
+    }
+}
+
 impl Transport for SendmailTransport {
     type Ok = ();
     type Error = Error;
 
     fn send_raw(&self, envelope: &Envelope, email: &[u8]) -> Result<Self::Ok, Self::Error> {
-        // Spawn the sendmail command
-        let mut process = self.command(envelope).spawn()?;
+        #[cfg(feature = "tracing")]
+        tracing::debug!(command = ?self.command, "sending email with");
 
-        process.stdin.as_mut().unwrap().write_all(email)?;
-        let output = process.wait_with_output()?;
+        // Spawn the sendmail command
+        let mut process = self.command(envelope).spawn().map_err(error::client)?;
+
+        process
+            .stdin
+            .as_mut()
+            .unwrap()
+            .write_all(email)
+            .map_err(error::client)?;
+        let output = process.wait_with_output().map_err(error::client)?;
 
         if output.status.success() {
             Ok(())
         } else {
-            Err(error::Error::Client(String::from_utf8(output.stderr)?))
+            let stderr = String::from_utf8(output.stderr).map_err(error::response)?;
+            Err(error::client(stderr))
         }
     }
 }
 
 #[cfg(feature = "async-std1")]
 #[async_trait]
-impl AsyncStd1Transport for SendmailTransport {
+impl AsyncTransport for AsyncSendmailTransport<AsyncStd1Executor> {
     type Ok = ();
     type Error = Error;
 
     async fn send_raw(&self, envelope: &Envelope, email: &[u8]) -> Result<Self::Ok, Self::Error> {
         use async_std::io::prelude::WriteExt;
 
+        #[cfg(feature = "tracing")]
+        tracing::debug!(command = ?self.inner.command, "sending email with");
+
         let mut command = self.async_std_command(envelope);
 
         // Spawn the sendmail command
-        let mut process = command.spawn()?;
+        let mut process = command.spawn().map_err(error::client)?;
 
-        process.stdin.as_mut().unwrap().write_all(&email).await?;
-        let output = process.output().await?;
+        process
+            .stdin
+            .as_mut()
+            .unwrap()
+            .write_all(email)
+            .await
+            .map_err(error::client)?;
+        let output = process.output().await.map_err(error::client)?;
 
         if output.status.success() {
             Ok(())
         } else {
-            Err(Error::Client(String::from_utf8(output.stderr)?))
-        }
-    }
-}
-
-#[cfg(feature = "tokio02")]
-#[async_trait]
-impl Tokio02Transport for SendmailTransport {
-    type Ok = ();
-    type Error = Error;
-
-    async fn send_raw(&self, envelope: &Envelope, email: &[u8]) -> Result<Self::Ok, Self::Error> {
-        use tokio02_crate::io::AsyncWriteExt;
-
-        let mut command = self.tokio02_command(envelope);
-
-        // Spawn the sendmail command
-        let mut process = command.spawn()?;
-
-        process.stdin.as_mut().unwrap().write_all(&email).await?;
-        let output = process.wait_with_output().await?;
-
-        if output.status.success() {
-            Ok(())
-        } else {
-            Err(Error::Client(String::from_utf8(output.stderr)?))
+            let stderr = String::from_utf8(output.stderr).map_err(error::response)?;
+            Err(error::client(stderr))
         }
     }
 }
 
 #[cfg(feature = "tokio1")]
 #[async_trait]
-impl Tokio1Transport for SendmailTransport {
+impl AsyncTransport for AsyncSendmailTransport<Tokio1Executor> {
     type Ok = ();
     type Error = Error;
 
     async fn send_raw(&self, envelope: &Envelope, email: &[u8]) -> Result<Self::Ok, Self::Error> {
         use tokio1_crate::io::AsyncWriteExt;
 
+        #[cfg(feature = "tracing")]
+        tracing::debug!(command = ?self.inner.command, "sending email with");
+
         let mut command = self.tokio1_command(envelope);
 
         // Spawn the sendmail command
-        let mut process = command.spawn()?;
+        let mut process = command.spawn().map_err(error::client)?;
 
-        process.stdin.as_mut().unwrap().write_all(&email).await?;
-        let output = process.wait_with_output().await?;
+        process
+            .stdin
+            .as_mut()
+            .unwrap()
+            .write_all(email)
+            .await
+            .map_err(error::client)?;
+        let output = process.wait_with_output().await.map_err(error::client)?;
 
         if output.status.success() {
             Ok(())
         } else {
-            Err(Error::Client(String::from_utf8(output.stderr)?))
+            let stderr = String::from_utf8(output.stderr).map_err(error::response)?;
+            Err(error::client(stderr))
         }
     }
 }

src/transport/smtp/async_transport.rs

@@ -1,28 +1,70 @@
+#[cfg(feature = "pool")]
+use std::sync::Arc;
+use std::{
+    fmt::{self, Debug},
+    marker::PhantomData,
+    time::Duration,
+};
+
 use async_trait::async_trait;
 
-#[cfg(any(feature = "tokio02", feature = "tokio1", feature = "async-std1"))]
+#[cfg(feature = "pool")]
+use super::pool::async_impl::Pool;
+#[cfg(feature = "pool")]
+use super::PoolConfig;
+#[cfg(any(
+    feature = "tokio1-native-tls",
+    feature = "tokio1-rustls",
+    feature = "async-std1-rustls"
+))]
 use super::Tls;
 use super::{
     client::AsyncSmtpConnection, ClientId, Credentials, Error, Mechanism, Response, SmtpInfo,
 };
 #[cfg(feature = "async-std1")]
-use crate::AsyncStd1Transport;
-use crate::Envelope;
-#[cfg(feature = "tokio02")]
-use crate::Tokio02Transport;
+use crate::AsyncStd1Executor;
+#[cfg(any(feature = "tokio1", feature = "async-std1"))]
+use crate::AsyncTransport;
 #[cfg(feature = "tokio1")]
-use crate::Tokio1Transport;
+use crate::Tokio1Executor;
+use crate::{Envelope, Executor};
 
-#[allow(missing_debug_implementations)]
-#[derive(Clone)]
-pub struct AsyncSmtpTransport<C> {
-    // TODO: pool
-    inner: AsyncSmtpClient<C>,
+/// Asynchronously sends emails using the SMTP protocol
+///
+/// `AsyncSmtpTransport` is the primary way for communicating
+/// with SMTP relay servers to send email messages. It holds the
+/// client connect configuration and creates new connections
+/// as necessary.
+///
+/// # Connection pool
+///
+/// When the `pool` feature is enabled (default), `AsyncSmtpTransport` maintains a
+/// connection pool to manage SMTP connections. The pool:
+///
+/// - Establishes a new connection when sending a message.
+/// - Recycles connections internally after a message is sent.
+/// - Reuses connections for subsequent messages, reducing connection setup overhead.
+///
+/// The connection pool can grow to hold multiple SMTP connections if multiple
+/// emails are sent concurrently, as SMTP does not support multiplexing within a
+/// single connection.
+///
+/// However, **connection reuse is not possible** if the `SyncSmtpTransport` instance
+/// is dropped after every email send operation. You must reuse the instance
+/// of this struct for the connection pool to be of any use.
+///
+/// To customize connection pool settings, use [`AsyncSmtpTransportBuilder::pool_config`].
+#[cfg_attr(docsrs, doc(cfg(any(feature = "tokio1", feature = "async-std1"))))]
+pub struct AsyncSmtpTransport<E: Executor> {
+    #[cfg(feature = "pool")]
+    inner: Arc<Pool<E>>,
+    #[cfg(not(feature = "pool"))]
+    inner: AsyncSmtpClient<E>,
 }
 
-#[cfg(feature = "tokio02")]
+#[cfg(feature = "tokio1")]
 #[async_trait]
-impl Tokio02Transport for AsyncSmtpTransport<Tokio02Connector> {
+impl AsyncTransport for AsyncSmtpTransport<Tokio1Executor> {
     type Ok = Response;
     type Error = Error;
 
@@ -32,33 +74,21 @@ impl Tokio02Transport for AsyncSmtpTransport<Tokio02Connector> {
 
         let result = conn.send(envelope, email).await?;
 
-        conn.quit().await?;
+        #[cfg(not(feature = "pool"))]
+        conn.abort().await;
 
         Ok(result)
     }
-}
 
-#[cfg(feature = "tokio1")]
-#[async_trait]
-impl Tokio1Transport for AsyncSmtpTransport<Tokio1Connector> {
-    type Ok = Response;
-    type Error = Error;
-
-    /// Sends an email
-    async fn send_raw(&self, envelope: &Envelope, email: &[u8]) -> Result<Self::Ok, Self::Error> {
-        let mut conn = self.inner.connection().await?;
-
-        let result = conn.send(envelope, email).await?;
-
-        conn.quit().await?;
-
-        Ok(result)
+    async fn shutdown(&self) {
+        #[cfg(feature = "pool")]
+        self.inner.shutdown().await;
     }
 }
 
 #[cfg(feature = "async-std1")]
 #[async_trait]
-impl AsyncStd1Transport for AsyncSmtpTransport<AsyncStd1Connector> {
+impl AsyncTransport for AsyncSmtpTransport<AsyncStd1Executor> {
     type Ok = Response;
     type Error = Error;
 
@@ -72,11 +102,16 @@ impl AsyncStd1Transport for AsyncSmtpTransport<AsyncStd1Connector> {
 
         Ok(result)
     }
+
+    async fn shutdown(&self) {
+        #[cfg(feature = "pool")]
+        self.inner.shutdown().await;
+    }
 }
 
-impl<C> AsyncSmtpTransport<C>
+impl<E> AsyncSmtpTransport<E>
 where
-    C: AsyncSmtpConnector,
+    E: Executor,
 {
     /// Simple and secure transport, using TLS connections to communicate with the SMTP server
     ///
@@ -85,15 +120,20 @@ where
     /// Creates an encrypted transport over submissions port, using the provided domain
     /// to validate TLS certificates.
     #[cfg(any(
-        feature = "tokio02-native-tls",
-        feature = "tokio02-rustls-tls",
         feature = "tokio1-native-tls",
-        feature = "tokio1-rustls-tls",
-        feature = "async-std1-native-tls",
-        feature = "async-std1-rustls-tls"
+        feature = "tokio1-rustls",
+        feature = "async-std1-rustls"
     ))]
+    #[cfg_attr(
+        docsrs,
+        doc(cfg(any(
+            feature = "tokio1-native-tls",
+            feature = "tokio1-rustls",
+            feature = "async-std1-rustls"
+        )))
+    )]
     pub fn relay(relay: &str) -> Result<AsyncSmtpTransportBuilder, Error> {
-        use super::{TlsParameters, SUBMISSIONS_PORT};
+        use super::{Tls, TlsParameters, SUBMISSIONS_PORT};
 
         let tls_parameters = TlsParameters::new(relay.into())?;
 
@@ -102,7 +142,7 @@ where
             .tls(Tls::Wrapper(tls_parameters)))
     }
 
-    /// Simple an secure transport, using STARTTLS to obtain encrypted connections
+    /// Simple and secure transport, using STARTTLS to obtain encrypted connections
     ///
     /// Alternative to [`AsyncSmtpTransport::relay`](#method.relay), for SMTP servers
     /// that don't take SMTPS connections.
@@ -114,15 +154,20 @@ where
     /// An error is returned if the connection can't be upgraded. No credentials
     /// or emails will be sent to the server, protecting from downgrade attacks.
     #[cfg(any(
-        feature = "tokio02-native-tls",
-        feature = "tokio02-rustls-tls",
         feature = "tokio1-native-tls",
-        feature = "tokio1-rustls-tls",
-        feature = "async-std1-native-tls",
-        feature = "async-std1-rustls-tls"
+        feature = "tokio1-rustls",
+        feature = "async-std1-rustls"
     ))]
+    #[cfg_attr(
+        docsrs,
+        doc(cfg(any(
+            feature = "tokio1-native-tls",
+            feature = "tokio1-rustls",
+            feature = "async-std1-rustls"
+        )))
+    )]
     pub fn starttls_relay(relay: &str) -> Result<AsyncSmtpTransportBuilder, Error> {
-        use super::{TlsParameters, SUBMISSION_PORT};
+        use super::{Tls, TlsParameters, SUBMISSION_PORT};
 
         let tls_parameters = TlsParameters::new(relay.into())?;
 
@@ -134,7 +179,7 @@ where
     /// Creates a new local SMTP client to port 25
     ///
     /// Shortcut for local unencrypted relay (typical local email daemon that will handle relaying)
-    pub fn unencrypted_localhost() -> AsyncSmtpTransport<C> {
+    pub fn unencrypted_localhost() -> AsyncSmtpTransport<E> {
         Self::builder_dangerous("localhost").build()
     }
 
@@ -144,37 +189,195 @@ where
     ///
     /// * No authentication
     /// * No TLS
+    /// * A 60-seconds timeout for smtp commands
     /// * Port 25
     ///
     /// Consider using [`AsyncSmtpTransport::relay`](#method.relay) or
     /// [`AsyncSmtpTransport::starttls_relay`](#method.starttls_relay) instead,
     /// if possible.
     pub fn builder_dangerous<T: Into<String>>(server: T) -> AsyncSmtpTransportBuilder {
-        let new = SmtpInfo {
-            server: server.into(),
-            ..Default::default()
-        };
-        AsyncSmtpTransportBuilder { info: new }
+        AsyncSmtpTransportBuilder::new(server)
+    }
+
+    /// Creates a `AsyncSmtpTransportBuilder` from a connection URL
+    ///
+    /// The protocol, credentials, host, port and EHLO name can be provided
+    /// in a single URL. This may be simpler than having to configure SMTP
+    /// through multiple configuration parameters and then having to pass
+    /// those options to lettre.
+    ///
+    /// The URL is created in the following way:
+    /// `scheme://user:pass@hostname:port/ehlo-name?tls=TLS`.
+    ///
+    /// `user` (Username) and `pass` (Password) are optional in case the
+    /// SMTP relay doesn't require authentication. When `port` is not
+    /// configured it is automatically determined based on the `scheme`.
+    /// `ehlo-name` optionally overwrites the hostname sent for the EHLO
+    /// command. `TLS` controls whether STARTTLS is simply enabled
+    /// (`opportunistic` - not enough to prevent man-in-the-middle attacks)
+    /// or `required` (require the server to upgrade the connection to
+    /// STARTTLS, otherwise fail on suspicion of main-in-the-middle attempt).
+    ///
+    /// Use the following table to construct your SMTP url:
+    ///
+    /// | scheme  | `tls` query parameter | example                                            | default port | remarks                                                                                                                               |
+    /// | ------- | --------------------- | -------------------------------------------------- | ------------ | ------------------------------------------------------------------------------------------------------------------------------------- |
+    /// | `smtps` | unset                 | `smtps://user:pass@hostname:port`                  | 465          | SMTP over TLS, recommended method                                                                                                     |
+    /// | `smtp`  | `required`            | `smtp://user:pass@hostname:port?tls=required`      | 587          | SMTP with STARTTLS required, when SMTP over TLS is not available                                                                      |
+    /// | `smtp`  | `opportunistic`       | `smtp://user:pass@hostname:port?tls=opportunistic` | 587          | SMTP with optionally STARTTLS when supported by the server. Not suitable for production use: vulnerable to a man-in-the-middle attack |
+    /// | `smtp`  | unset                 | `smtp://user:pass@hostname:port`                   | 587          | Always unencrypted SMTP. Not suitable for production use: sends all data unencrypted                                                  |
+    ///
+    /// IMPORTANT: some parameters like `user` and `pass` cannot simply
+    /// be concatenated to construct the final URL because special characters
+    /// contained within the parameter may confuse the URL decoder.
+    /// Manually URL encode the parameters before concatenating them or use
+    /// a proper URL encoder, like the following cargo script:
+    ///
+    /// ```rust
+    /// # let _ = r#"
+    /// #!/usr/bin/env cargo
+    ///
+    /// //! ```cargo
+    /// //! [dependencies]
+    /// //! url = "2"
+    /// //! ```
+    /// # "#;
+    ///
+    /// use url::Url;
+    ///
+    /// fn main() {
+    ///     // don't touch this line
+    ///     let mut url = Url::parse("foo://bar").unwrap();
+    ///
+    ///     // configure the scheme (`smtp` or `smtps`) here.
+    ///     url.set_scheme("smtps").unwrap();
+    ///     // configure the username and password.
+    ///     // remove the following two lines if unauthenticated.
+    ///     url.set_username("username").unwrap();
+    ///     url.set_password(Some("password")).unwrap();
+    ///     // configure the hostname
+    ///     url.set_host(Some("smtp.example.com")).unwrap();
+    ///     // configure the port - only necessary if using a non-default port
+    ///     url.set_port(Some(465)).unwrap();
+    ///     // configure the EHLO name
+    ///     url.set_path("ehlo-name");
+    ///
+    ///     println!("{url}");
+    /// }
+    /// ```
+    ///
+    /// The connection URL can then be used in the following way:
+    ///
+    /// ```rust,no_run
+    /// use lettre::{
+    ///     message::header::ContentType, transport::smtp::authentication::Credentials,
+    ///     AsyncSmtpTransport, AsyncTransport, Message, Tokio1Executor,
+    /// };
+    /// # use tokio1_crate as tokio;
+    ///
+    /// # #[tokio::main]
+    /// # async fn main() -> Result<(), Box<dyn std::error::Error>> {
+    /// let email = Message::builder()
+    ///     .from("NoBody <nobody@domain.tld>".parse().unwrap())
+    ///     .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
+    ///     .to("Hei <hei@domain.tld>".parse().unwrap())
+    ///     .subject("Happy new year")
+    ///     .header(ContentType::TEXT_PLAIN)
+    ///     .body(String::from("Be happy!"))
+    ///     .unwrap();
+    ///
+    /// // Open a remote connection to gmail
+    /// let mailer: AsyncSmtpTransport<Tokio1Executor> =
+    ///     AsyncSmtpTransport::<Tokio1Executor>::from_url(
+    ///         "smtps://username:password@smtp.example.com:465",
+    ///     )?
+    ///     .build();
+    ///
+    /// // Send the email
+    /// mailer.send(email).await?;
+    /// # Ok(())
+    /// # }
+    /// ```
+    #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+    #[cfg_attr(
+        docsrs,
+        doc(cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls")))
+    )]
+    pub fn from_url(connection_url: &str) -> Result<AsyncSmtpTransportBuilder, Error> {
+        super::connection_url::from_connection_url(connection_url)
+    }
+
+    /// Tests the SMTP connection
+    ///
+    /// `test_connection()` tests the connection by using the SMTP NOOP command.
+    /// The connection is closed afterward if a connection pool is not used.
+    pub async fn test_connection(&self) -> Result<bool, Error> {
+        let mut conn = self.inner.connection().await?;
+
+        let is_connected = conn.test_connected().await;
+
+        #[cfg(not(feature = "pool"))]
+        conn.quit().await?;
+
+        Ok(is_connected)
+    }
+}
+
+impl<E: Executor> Debug for AsyncSmtpTransport<E> {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        let mut builder = f.debug_struct("AsyncSmtpTransport");
+        builder.field("inner", &self.inner);
+        builder.finish()
+    }
+}
+
+impl<E> Clone for AsyncSmtpTransport<E>
+where
+    E: Executor,
+{
+    fn clone(&self) -> Self {
+        Self {
+            #[cfg(feature = "pool")]
+            inner: Arc::clone(&self.inner),
+            #[cfg(not(feature = "pool"))]
+            inner: self.inner.clone(),
+        }
     }
 }
 
 /// Contains client configuration.
 /// Instances of this struct can be created using functions of [`AsyncSmtpTransport`].
-#[allow(missing_debug_implementations)]
-#[derive(Clone)]
+#[derive(Debug, Clone)]
+#[cfg_attr(docsrs, doc(cfg(any(feature = "tokio1", feature = "async-std1"))))]
 pub struct AsyncSmtpTransportBuilder {
     info: SmtpInfo,
+    #[cfg(feature = "pool")]
+    pool_config: PoolConfig,
 }
 
 /// Builder for the SMTP `AsyncSmtpTransport`
 impl AsyncSmtpTransportBuilder {
+    // Create new builder with default parameters
+    pub(crate) fn new<T: Into<String>>(server: T) -> Self {
+        let info = SmtpInfo {
+            server: server.into(),
+            ..Default::default()
+        };
+
+        AsyncSmtpTransportBuilder {
+            info,
+            #[cfg(feature = "pool")]
+            pool_config: PoolConfig::default(),
+        }
+    }
+
     /// Set the name used during EHLO
     pub fn hello_name(mut self, name: ClientId) -> Self {
         self.info.hello_name = name;
         self
     }
 
-    /// Set the authentication mechanism to use
+    /// Set the authentication credentials to use
     pub fn credentials(mut self, credentials: Credentials) -> Self {
         self.info.credentials = Some(credentials);
         self
@@ -187,215 +390,133 @@ impl AsyncSmtpTransportBuilder {
     }
 
     /// Set the port to use
+    ///
+    /// # ⚠️⚠️⚠️ You probably don't need to call this method ⚠️⚠️⚠️
+    ///
+    /// lettre usually picks the correct `port` when building
+    /// [`AsyncSmtpTransport`] using [`AsyncSmtpTransport::relay`] or
+    /// [`AsyncSmtpTransport::starttls_relay`].
+    ///
+    /// # Errors
+    ///
+    /// Using the incorrect `port` and [`Self::tls`] combination may
+    /// lead to hard to debug IO errors coming from the TLS library.
     pub fn port(mut self, port: u16) -> Self {
         self.info.port = port;
         self
     }
 
+    /// Set the timeout duration
+    pub fn timeout(mut self, timeout: Option<Duration>) -> Self {
+        self.info.timeout = timeout;
+        self
+    }
+
     /// Set the TLS settings to use
+    ///
+    /// # ⚠️⚠️⚠️ You probably don't need to call this method ⚠️⚠️⚠️
+    ///
+    /// By default lettre chooses the correct `tls` configuration when
+    /// building [`AsyncSmtpTransport`] using [`AsyncSmtpTransport::relay`] or
+    /// [`AsyncSmtpTransport::starttls_relay`].
+    ///
+    /// # Errors
+    ///
+    /// Using the incorrect [`Tls`] and [`Self::port`] combination may
+    /// lead to hard to debug IO errors coming from the TLS library.
     #[cfg(any(
-        feature = "tokio02-native-tls",
-        feature = "tokio02-rustls-tls",
         feature = "tokio1-native-tls",
-        feature = "tokio1-rustls-tls",
-        feature = "async-std1-native-tls",
-        feature = "async-std1-rustls-tls"
+        feature = "tokio1-rustls",
+        feature = "async-std1-rustls"
     ))]
+    #[cfg_attr(
+        docsrs,
+        doc(cfg(any(
+            feature = "tokio1-native-tls",
+            feature = "tokio1-rustls",
+            feature = "async-std1-rustls"
+        )))
+    )]
     pub fn tls(mut self, tls: Tls) -> Self {
         self.info.tls = tls;
         self
     }
 
-    /// Build the transport (with default pool if enabled)
-    pub fn build<C>(self) -> AsyncSmtpTransport<C>
+    /// Use a custom configuration for the connection pool
+    ///
+    /// Defaults can be found at [`PoolConfig`]
+    #[cfg(feature = "pool")]
+    #[cfg_attr(docsrs, doc(cfg(feature = "pool")))]
+    pub fn pool_config(mut self, pool_config: PoolConfig) -> Self {
+        self.pool_config = pool_config;
+        self
+    }
+
+    /// Build the transport
+    pub fn build<E>(self) -> AsyncSmtpTransport<E>
     where
-        C: AsyncSmtpConnector,
+        E: Executor,
     {
-        let connector = Default::default();
         let client = AsyncSmtpClient {
-            connector,
             info: self.info,
+            marker_: PhantomData,
         };
+
+        #[cfg(feature = "pool")]
+        let client = Pool::new(self.pool_config, client);
+
         AsyncSmtpTransport { inner: client }
     }
 }
 
 /// Build client
-#[derive(Clone)]
-pub struct AsyncSmtpClient<C> {
-    connector: C,
+pub(super) struct AsyncSmtpClient<E> {
     info: SmtpInfo,
+    marker_: PhantomData<E>,
 }
 
-impl<C> AsyncSmtpClient<C>
+impl<E> AsyncSmtpClient<E>
 where
-    C: AsyncSmtpConnector,
+    E: Executor,
 {
     /// Creates a new connection directly usable to send emails
     ///
     /// Handles encryption and authentication
-    pub async fn connection(&self) -> Result<AsyncSmtpConnection, Error> {
-        let mut conn = C::connect(
+    pub(super) async fn connection(&self) -> Result<AsyncSmtpConnection, Error> {
+        let mut conn = E::connect(
             &self.info.server,
             self.info.port,
+            self.info.timeout,
             &self.info.hello_name,
             &self.info.tls,
         )
         .await?;
 
         if let Some(credentials) = &self.info.credentials {
-            conn.auth(&self.info.authentication, &credentials).await?;
+            conn.auth(&self.info.authentication, credentials).await?;
         }
         Ok(conn)
     }
 }
 
-#[async_trait]
-pub trait AsyncSmtpConnector: Default + private::Sealed {
-    async fn connect(
-        hostname: &str,
-        port: u16,
-        hello_name: &ClientId,
-        tls: &Tls,
-    ) -> Result<AsyncSmtpConnection, Error>;
-}
-
-#[derive(Debug, Copy, Clone, Default)]
-#[cfg(feature = "tokio02")]
-#[cfg_attr(docsrs, doc(cfg(feature = "tokio02")))]
-pub struct Tokio02Connector;
-
-#[async_trait]
-#[cfg(feature = "tokio02")]
-impl AsyncSmtpConnector for Tokio02Connector {
-    async fn connect(
-        hostname: &str,
-        port: u16,
-        hello_name: &ClientId,
-        tls: &Tls,
-    ) -> Result<AsyncSmtpConnection, Error> {
-        #[allow(clippy::match_single_binding)]
-        let tls_parameters = match tls {
-            #[cfg(any(feature = "tokio02-native-tls", feature = "tokio02-rustls-tls"))]
-            Tls::Wrapper(ref tls_parameters) => Some(tls_parameters.clone()),
-            _ => None,
-        };
-        #[allow(unused_mut)]
-        let mut conn =
-            AsyncSmtpConnection::connect_tokio02(hostname, port, hello_name, tls_parameters)
-                .await?;
-
-        #[cfg(any(feature = "tokio02-native-tls", feature = "tokio02-rustls-tls"))]
-        match tls {
-            Tls::Opportunistic(ref tls_parameters) => {
-                if conn.can_starttls() {
-                    conn.starttls(tls_parameters.clone(), hello_name).await?;
-                }
-            }
-            Tls::Required(ref tls_parameters) => {
-                conn.starttls(tls_parameters.clone(), hello_name).await?;
-            }
-            _ => (),
-        }
-
-        Ok(conn)
+impl<E> Debug for AsyncSmtpClient<E> {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        let mut builder = f.debug_struct("AsyncSmtpClient");
+        builder.field("info", &self.info);
+        builder.finish()
     }
 }
 
-#[derive(Debug, Copy, Clone, Default)]
-#[cfg(feature = "tokio1")]
-#[cfg_attr(docsrs, doc(cfg(feature = "tokio1")))]
-pub struct Tokio1Connector;
-
-#[async_trait]
-#[cfg(feature = "tokio1")]
-impl AsyncSmtpConnector for Tokio1Connector {
-    async fn connect(
-        hostname: &str,
-        port: u16,
-        hello_name: &ClientId,
-        tls: &Tls,
-    ) -> Result<AsyncSmtpConnection, Error> {
-        #[allow(clippy::match_single_binding)]
-        let tls_parameters = match tls {
-            #[cfg(any(feature = "tokio1-native-tls", feature = "tokio1-rustls-tls"))]
-            Tls::Wrapper(ref tls_parameters) => Some(tls_parameters.clone()),
-            _ => None,
-        };
-        #[allow(unused_mut)]
-        let mut conn =
-            AsyncSmtpConnection::connect_tokio1(hostname, port, hello_name, tls_parameters).await?;
-
-        #[cfg(any(feature = "tokio1-native-tls", feature = "tokio1-rustls-tls"))]
-        match tls {
-            Tls::Opportunistic(ref tls_parameters) => {
-                if conn.can_starttls() {
-                    conn.starttls(tls_parameters.clone(), hello_name).await?;
-                }
-            }
-            Tls::Required(ref tls_parameters) => {
-                conn.starttls(tls_parameters.clone(), hello_name).await?;
-            }
-            _ => (),
+// `clone` is unused when the `pool` feature is on
+#[allow(dead_code)]
+impl<E> AsyncSmtpClient<E>
+where
+    E: Executor,
+{
+    fn clone(&self) -> Self {
+        Self {
+            info: self.info.clone(),
+            marker_: PhantomData,
         }
-
-        Ok(conn)
     }
 }
-
-#[derive(Debug, Copy, Clone, Default)]
-#[cfg(feature = "async-std1")]
-#[cfg_attr(docsrs, doc(cfg(feature = "async-std1")))]
-pub struct AsyncStd1Connector;
-
-#[async_trait]
-#[cfg(feature = "async-std1")]
-impl AsyncSmtpConnector for AsyncStd1Connector {
-    async fn connect(
-        hostname: &str,
-        port: u16,
-        hello_name: &ClientId,
-        tls: &Tls,
-    ) -> Result<AsyncSmtpConnection, Error> {
-        #[allow(clippy::match_single_binding)]
-        let tls_parameters = match tls {
-            #[cfg(any(feature = "async-std1-native-tls", feature = "async-std1-rustls-tls"))]
-            Tls::Wrapper(ref tls_parameters) => Some(tls_parameters.clone()),
-            _ => None,
-        };
-        #[allow(unused_mut)]
-        let mut conn =
-            AsyncSmtpConnection::connect_asyncstd1(hostname, port, hello_name, tls_parameters)
-                .await?;
-
-        #[cfg(any(feature = "async-std1-native-tls", feature = "async-std1-rustls-tls"))]
-        match tls {
-            Tls::Opportunistic(ref tls_parameters) => {
-                if conn.can_starttls() {
-                    conn.starttls(tls_parameters.clone(), hello_name).await?;
-                }
-            }
-            Tls::Required(ref tls_parameters) => {
-                conn.starttls(tls_parameters.clone(), hello_name).await?;
-            }
-            _ => (),
-        }
-
-        Ok(conn)
-    }
-}
-
-mod private {
-    use super::*;
-
-    pub trait Sealed {}
-
-    #[cfg(feature = "tokio02")]
-    impl Sealed for Tokio02Connector {}
-
-    #[cfg(feature = "tokio1")]
-    impl Sealed for Tokio1Connector {}
-
-    #[cfg(feature = "async-std1")]
-    impl Sealed for AsyncStd1Connector {}
-}

src/transport/smtp/authentication.rs

@@ -1,14 +1,16 @@
 //! Provides limited SASL authentication mechanisms
 
-use crate::transport::smtp::error::Error;
-use std::fmt::{self, Display, Formatter};
+use std::fmt::{self, Debug, Display, Formatter};
+
+use crate::transport::smtp::error::{self, Error};
 
 /// Accepted authentication mechanisms
+///
 /// Trying LOGIN last as it is deprecated.
 pub const DEFAULT_MECHANISMS: &[Mechanism] = &[Mechanism::Plain, Mechanism::Login];
 
 /// Contains user credentials
-#[derive(PartialEq, Eq, Clone, Hash, Debug)]
+#[derive(PartialEq, Eq, Clone, Hash)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 pub struct Credentials {
     authentication_identity: String,
@@ -17,6 +19,9 @@ pub struct Credentials {
 
 impl Credentials {
     /// Create a `Credentials` struct from username and password
+    ///
+    /// When using [`Mechanism::Xoauth2`], `password` is the raw
+    /// bearer access token.
     pub fn new(username: String, password: String) -> Credentials {
         Credentials {
             authentication_identity: username,
@@ -35,19 +40,26 @@ where
     }
 }
 
+impl Debug for Credentials {
+    fn fmt(&self, f: &mut Formatter<'_>) -> fmt::Result {
+        f.debug_struct("Credentials").finish()
+    }
+}
+
 /// Represents authentication mechanisms
 #[derive(PartialEq, Eq, Copy, Clone, Hash, Debug)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 pub enum Mechanism {
-    /// PLAIN authentication mechanism
-    /// RFC 4616: https://tools.ietf.org/html/rfc4616
+    /// PLAIN authentication mechanism, defined in
+    /// [RFC 4616](https://tools.ietf.org/html/rfc4616)
     Plain,
     /// LOGIN authentication mechanism
-    /// Obsolete but needed for some providers (like office365)
-    /// https://www.ietf.org/archive/id/draft-murchison-sasl-login-00.txt
+    /// Obsolete but needed for some providers (like Office 365)
+    ///
+    /// Defined in [draft-murchison-sasl-login-00](https://www.ietf.org/archive/id/draft-murchison-sasl-login-00.txt).
     Login,
-    /// Non-standard XOAUTH2 mechanism
-    /// https://developers.google.com/gmail/imap/xoauth2-protocol
+    /// Non-standard XOAUTH2 mechanism, defined in
+    /// [xoauth2-protocol](https://developers.google.com/gmail/imap/xoauth2-protocol)
     Xoauth2,
 }
 
@@ -62,7 +74,7 @@ impl Display for Mechanism {
 }
 
 impl Mechanism {
-    /// Does the mechanism supports initial response
+    /// Does the mechanism support initial response?
     pub fn supports_initial_response(self) -> bool {
         match self {
             Mechanism::Plain | Mechanism::Xoauth2 => true,
@@ -79,28 +91,34 @@ impl Mechanism {
     ) -> Result<String, Error> {
         match self {
             Mechanism::Plain => match challenge {
-                Some(_) => Err(Error::Client("This mechanism does not expect a challenge")),
+                Some(_) => Err(error::client("This mechanism does not expect a challenge")),
                 None => Ok(format!(
                     "\u{0}{}\u{0}{}",
                     credentials.authentication_identity, credentials.secret
                 )),
             },
             Mechanism::Login => {
-                let decoded_challenge =
-                    challenge.ok_or(Error::Client("This mechanism does expect a challenge"))?;
+                let decoded_challenge = challenge
+                    .ok_or_else(|| error::client("This mechanism does expect a challenge"))?;
 
-                if vec!["User Name", "Username:", "Username"].contains(&decoded_challenge) {
-                    return Ok(credentials.authentication_identity.to_string());
+                if contains_ignore_ascii_case(
+                    decoded_challenge,
+                    ["User Name", "Username:", "Username", "User Name\0"],
+                ) {
+                    return Ok(credentials.authentication_identity.clone());
                 }
 
-                if vec!["Password", "Password:"].contains(&decoded_challenge) {
-                    return Ok(credentials.secret.to_string());
+                if contains_ignore_ascii_case(
+                    decoded_challenge,
+                    ["Password", "Password:", "Password\0"],
+                ) {
+                    return Ok(credentials.secret.clone());
                 }
 
-                Err(Error::Client("Unrecognized challenge"))
+                Err(error::client("Unrecognized challenge"))
             }
             Mechanism::Xoauth2 => match challenge {
-                Some(_) => Err(Error::Client("This mechanism does not expect a challenge")),
+                Some(_) => Err(error::client("This mechanism does not expect a challenge")),
                 None => Ok(format!(
                     "user={}\x01auth=Bearer {}\x01\x01",
                     credentials.authentication_identity, credentials.secret
@@ -110,6 +128,15 @@ impl Mechanism {
     }
 }
 
+fn contains_ignore_ascii_case<'a>(
+    haystack: &str,
+    needles: impl IntoIterator<Item = &'a str>,
+) -> bool {
+    needles
+        .into_iter()
+        .any(|item| item.eq_ignore_ascii_case(haystack))
+}
+
 #[cfg(test)]
 mod test {
     use super::{Credentials, Mechanism};
@@ -118,7 +145,7 @@ mod test {
     fn test_plain() {
         let mechanism = Mechanism::Plain;
 
-        let credentials = Credentials::new("username".to_string(), "password".to_string());
+        let credentials = Credentials::new("username".to_owned(), "password".to_owned());
 
         assert_eq!(
             mechanism.response(&credentials, None).unwrap(),
@@ -131,7 +158,7 @@ mod test {
     fn test_login() {
         let mechanism = Mechanism::Login;
 
-        let credentials = Credentials::new("alice".to_string(), "wonderland".to_string());
+        let credentials = Credentials::new("alice".to_owned(), "wonderland".to_owned());
 
         assert_eq!(
             mechanism.response(&credentials, Some("Username")).unwrap(),
@@ -144,13 +171,30 @@ mod test {
         assert!(mechanism.response(&credentials, None).is_err());
     }
 
+    #[test]
+    fn test_login_case_insensitive() {
+        let mechanism = Mechanism::Login;
+
+        let credentials = Credentials::new("alice".to_owned(), "wonderland".to_owned());
+
+        assert_eq!(
+            mechanism.response(&credentials, Some("username")).unwrap(),
+            "alice"
+        );
+        assert_eq!(
+            mechanism.response(&credentials, Some("password")).unwrap(),
+            "wonderland"
+        );
+        assert!(mechanism.response(&credentials, None).is_err());
+    }
+
     #[test]
     fn test_xoauth2() {
         let mechanism = Mechanism::Xoauth2;
 
         let credentials = Credentials::new(
-            "username".to_string(),
-            "vF9dft4qmTc2Nvb3RlckBhdHRhdmlzdGEuY29tCg==".to_string(),
+            "username".to_owned(),
+            "vF9dft4qmTc2Nvb3RlckBhdHRhdmlzdGEuY29tCg==".to_owned(),
         );
 
         assert_eq!(
@@ -163,7 +207,7 @@ mod test {
     #[test]
     fn test_from_user_pass_for_credentials() {
         assert_eq!(
-            Credentials::new("alice".to_string(), "wonderland".to_string()),
+            Credentials::new("alice".to_owned(), "wonderland".to_owned()),
             Credentials::from(("alice", "wonderland"))
         );
     }

src/transport/smtp/client/async_connection.rs

@@ -1,12 +1,18 @@
-use std::{fmt::Display, io};
+use std::{fmt::Display, net::IpAddr, time::Duration};
 
 use futures_util::io::{AsyncBufReadExt, AsyncWriteExt, BufReader};
 
-use super::{AsyncNetworkStream, ClientCodec, TlsParameters};
+#[cfg(feature = "tokio1")]
+use super::async_net::AsyncTokioStream;
+#[cfg(feature = "tracing")]
+use super::escape_crlf;
+#[allow(deprecated)]
+use super::{async_net::AsyncNetworkStream, ClientCodec, TlsParameters};
 use crate::{
     transport::smtp::{
         authentication::{Credentials, Mechanism},
-        commands::*,
+        commands::{Auth, Data, Ehlo, Mail, Noop, Quit, Rcpt, Starttls},
+        error,
         error::Error,
         extension::{ClientId, Extension, MailBodyParameter, MailParameter, ServerInfo},
         response::{parse_response, Response},
@@ -14,9 +20,6 @@ use crate::{
     Envelope,
 };
 
-#[cfg(feature = "tracing")]
-use super::escape_crlf;
-
 macro_rules! try_smtp (
     ($err: expr, $client: ident) => ({
         match $err {
@@ -33,6 +36,7 @@ macro_rules! try_smtp (
 pub struct AsyncSmtpConnection {
     /// TCP stream between client and server
     /// Value is None before connection
+    #[allow(deprecated)]
     stream: BufReader<AsyncNetworkStream>,
     /// Panic state
     panic: bool,
@@ -41,35 +45,66 @@ pub struct AsyncSmtpConnection {
 }
 
 impl AsyncSmtpConnection {
+    /// Get information about the server
     pub fn server_info(&self) -> &ServerInfo {
         &self.server_info
     }
 
-    /// Connects to the configured server
+    /// Connects with existing async stream
     ///
     /// Sends EHLO and parses server information
-    #[cfg(feature = "tokio02")]
-    pub async fn connect_tokio02(
-        hostname: &str,
-        port: u16,
+    #[cfg(feature = "tokio1")]
+    pub async fn connect_with_transport(
+        stream: Box<dyn AsyncTokioStream>,
         hello_name: &ClientId,
-        tls_parameters: Option<TlsParameters>,
     ) -> Result<AsyncSmtpConnection, Error> {
-        let stream = AsyncNetworkStream::connect_tokio02(hostname, port, tls_parameters).await?;
+        #[allow(deprecated)]
+        let stream = AsyncNetworkStream::use_existing_tokio1(stream);
         Self::connect_impl(stream, hello_name).await
     }
 
     /// Connects to the configured server
     ///
+    /// If `tls_parameters` is `Some`, then the connection will use Implicit TLS (sometimes
+    /// referred to as `SMTPS`). See also [`AsyncSmtpConnection::starttls`].
+    ///
+    /// If `local_address` is `Some`, then the address provided shall be used to bind the
+    /// connection to a specific local address using [`tokio1_crate::net::TcpSocket::bind`].
+    ///
     /// Sends EHLO and parses server information
+    ///
+    /// # Example
+    ///
+    /// ```no_run
+    /// # use std::time::Duration;
+    /// # use lettre::transport::smtp::{client::{AsyncSmtpConnection, TlsParameters}, extension::ClientId};
+    /// # use tokio1_crate::{self as tokio, net::ToSocketAddrs as _};
+    /// #
+    /// # #[tokio::main]
+    /// # async fn main() -> Result<(), Box<dyn std::error::Error>> {
+    /// let connection = AsyncSmtpConnection::connect_tokio1(
+    ///     ("example.com", 465),
+    ///     Some(Duration::from_secs(60)),
+    ///     &ClientId::default(),
+    ///     Some(TlsParameters::new("example.com".to_owned())?),
+    ///     None,
+    /// )
+    /// .await?;
+    /// # Ok(())
+    /// # }
+    /// ```
     #[cfg(feature = "tokio1")]
-    pub async fn connect_tokio1(
-        hostname: &str,
-        port: u16,
+    pub async fn connect_tokio1<T: tokio1_crate::net::ToSocketAddrs>(
+        server: T,
+        timeout: Option<Duration>,
         hello_name: &ClientId,
         tls_parameters: Option<TlsParameters>,
+        local_address: Option<IpAddr>,
     ) -> Result<AsyncSmtpConnection, Error> {
-        let stream = AsyncNetworkStream::connect_tokio1(hostname, port, tls_parameters).await?;
+        #[allow(deprecated)]
+        let stream =
+            AsyncNetworkStream::connect_tokio1(server, timeout, tls_parameters, local_address)
+                .await?;
         Self::connect_impl(stream, hello_name).await
     }
 
@@ -77,16 +112,18 @@ impl AsyncSmtpConnection {
     ///
     /// Sends EHLO and parses server information
     #[cfg(feature = "async-std1")]
-    pub async fn connect_asyncstd1(
-        hostname: &str,
-        port: u16,
+    pub async fn connect_asyncstd1<T: async_std::net::ToSocketAddrs>(
+        server: T,
+        timeout: Option<Duration>,
         hello_name: &ClientId,
         tls_parameters: Option<TlsParameters>,
     ) -> Result<AsyncSmtpConnection, Error> {
-        let stream = AsyncNetworkStream::connect_asyncstd1(hostname, port, tls_parameters).await?;
+        #[allow(deprecated)]
+        let stream = AsyncNetworkStream::connect_asyncstd1(server, timeout, tls_parameters).await?;
         Self::connect_impl(stream, hello_name).await
     }
 
+    #[allow(deprecated)]
     async fn connect_impl(
         stream: AsyncNetworkStream,
         hello_name: &ClientId,
@@ -112,9 +149,32 @@ impl AsyncSmtpConnection {
         // Mail
         let mut mail_options = vec![];
 
-        if self.server_info().supports_feature(Extension::EightBitMime) {
+        // Internationalization handling
+        //
+        // * 8BITMIME: https://tools.ietf.org/html/rfc6152
+        // * SMTPUTF8: https://tools.ietf.org/html/rfc653
+
+        // Check for non-ascii addresses and use the SMTPUTF8 option if any.
+        if envelope.has_non_ascii_addresses() {
+            if !self.server_info().supports_feature(Extension::SmtpUtfEight) {
+                // don't try to send non-ascii addresses (per RFC)
+                return Err(error::client(
+                    "Envelope contains non-ascii chars but server does not support SMTPUTF8",
+                ));
+            }
+            mail_options.push(MailParameter::SmtpUtfEight);
+        }
+
+        // Check for non-ascii content in the message
+        if !email.is_ascii() {
+            if !self.server_info().supports_feature(Extension::EightBitMime) {
+                return Err(error::client(
+                    "Message contains non-ascii chars but server does not support 8BITMIME",
+                ));
+            }
             mail_options.push(MailParameter::Body(MailBodyParameter::EightBitMime));
         }
+
         try_smtp!(
             self.command(Mail::new(envelope.from().cloned(), mail_options))
                 .await,
@@ -145,6 +205,12 @@ impl AsyncSmtpConnection {
         !self.is_encrypted() && self.server_info.supports_feature(Extension::StartTls)
     }
 
+    /// Upgrade the connection using `STARTTLS`.
+    ///
+    /// As described in [rfc3207]. Note that this mechanism has been deprecated in [rfc8314].
+    ///
+    /// [rfc3207]: https://www.rfc-editor.org/rfc/rfc3207
+    /// [rfc8314]: https://www.rfc-editor.org/rfc/rfc8314
     #[allow(unused_variables)]
     pub async fn starttls(
         &mut self,
@@ -153,17 +219,14 @@ impl AsyncSmtpConnection {
     ) -> Result<(), Error> {
         if self.server_info.supports_feature(Extension::StartTls) {
             try_smtp!(self.command(Starttls).await, self);
-            try_smtp!(
-                self.stream.get_mut().upgrade_tls(tls_parameters).await,
-                self
-            );
+            self.stream.get_mut().upgrade_tls(tls_parameters).await?;
             #[cfg(feature = "tracing")]
             tracing::debug!("connection encrypted");
             // Send EHLO again
             try_smtp!(self.ehlo(hello_name).await, self);
             Ok(())
         } else {
-            Err(Error::Client("STARTTLS is not supported on this server"))
+            Err(error::client("STARTTLS is not supported on this server"))
         }
     }
 
@@ -184,9 +247,11 @@ impl AsyncSmtpConnection {
             self.panic = true;
             let _ = self.command(Quit).await;
         }
+        let _ = self.stream.close().await;
     }
 
     /// Sets the underlying stream
+    #[allow(deprecated)]
     pub fn set_stream(&mut self, stream: AsyncNetworkStream) {
         self.stream = BufReader::new(stream);
     }
@@ -201,7 +266,7 @@ impl AsyncSmtpConnection {
         self.command(Noop).await.is_ok()
     }
 
-    /// Sends an AUTH command with the given mechanism, and handles challenge if needed
+    /// Sends an AUTH command with the given mechanism, and handles the challenge if needed
     pub async fn auth(
         &mut self,
         mechanisms: &[Mechanism],
@@ -210,12 +275,10 @@ impl AsyncSmtpConnection {
         let mechanism = self
             .server_info
             .get_auth_mechanism(mechanisms)
-            .ok_or(Error::Client(
-                "No compatible authentication mechanism was found",
-            ))?;
+            .ok_or_else(|| error::client("No compatible authentication mechanism was found"))?;
 
         // Limit challenges to avoid blocking
-        let mut challenges = 10;
+        let mut challenges: u8 = 10;
         let mut response = self
             .command(Auth::new(mechanism, credentials.clone(), None)?)
             .await?;
@@ -234,7 +297,7 @@ impl AsyncSmtpConnection {
         }
 
         if challenges == 0 {
-            Err(Error::ResponseParsing("Unexpected number of challenges"))
+            Err(error::response("Unexpected number of challenges"))
         } else {
             Ok(response)
         }
@@ -258,8 +321,16 @@ impl AsyncSmtpConnection {
 
     /// Writes a string to the server
     async fn write(&mut self, string: &[u8]) -> Result<(), Error> {
-        self.stream.get_mut().write_all(string).await?;
-        self.stream.get_mut().flush().await?;
+        self.stream
+            .get_mut()
+            .write_all(string)
+            .await
+            .map_err(error::network)?;
+        self.stream
+            .get_mut()
+            .flush()
+            .await
+            .map_err(error::network)?;
 
         #[cfg(feature = "tracing")]
         tracing::debug!("Wrote: {}", escape_crlf(&String::from_utf8_lossy(string)));
@@ -270,27 +341,64 @@ impl AsyncSmtpConnection {
     pub async fn read_response(&mut self) -> Result<Response, Error> {
         let mut buffer = String::with_capacity(100);
 
-        while self.stream.read_line(&mut buffer).await? > 0 {
+        while self
+            .stream
+            .read_line(&mut buffer)
+            .await
+            .map_err(error::network)?
+            > 0
+        {
             #[cfg(feature = "tracing")]
             tracing::debug!("<< {}", escape_crlf(&buffer));
             match parse_response(&buffer) {
                 Ok((_remaining, response)) => {
-                    if response.is_positive() {
-                        return Ok(response);
+                    return if response.is_positive() {
+                        Ok(response)
+                    } else {
+                        Err(error::code(
+                            response.code(),
+                            Some(response.message().collect()),
+                        ))
                     }
-
-                    return Err(response.into());
                 }
                 Err(nom::Err::Failure(e)) => {
-                    return Err(Error::Parsing(e.code));
+                    return Err(error::response(e.to_string()));
                 }
                 Err(nom::Err::Incomplete(_)) => { /* read more */ }
                 Err(nom::Err::Error(e)) => {
-                    return Err(Error::Parsing(e.code));
+                    return Err(error::response(e.to_string()));
                 }
             }
         }
 
-        Err(io::Error::new(io::ErrorKind::Other, "incomplete").into())
+        Err(error::response("incomplete response"))
+    }
+
+    /// The X509 certificate of the server (DER encoded)
+    #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+    pub fn peer_certificate(&self) -> Result<Vec<u8>, Error> {
+        self.stream.get_ref().peer_certificate()
+    }
+
+    /// Currently this is only avaialable when using Boring TLS and
+    /// returns the result of the verification of the TLS certificate
+    /// presented by the peer, if any. Only the last error encountered
+    /// during verification is presented.
+    /// It can be useful when you don't want to fail outright the TLS
+    /// negotiation, for example when a self-signed certificate is
+    /// encountered, but still want to record metrics or log the fact.
+    /// When using DANE verification, the PKI root of trust moves from
+    /// the CAs to DNS, so self-signed certificates are permitted as long
+    /// as the TLSA records match the leaf or issuer certificates.
+    /// It cannot be called on non Boring TLS streams.
+    #[cfg(feature = "boring-tls")]
+    pub fn tls_verify_result(&self) -> Result<(), Error> {
+        self.stream.get_ref().tls_verify_result()
+    }
+
+    /// All the X509 certificates of the chain (DER encoded)
+    #[cfg(any(feature = "rustls", feature = "boring-tls"))]
+    pub fn certificate_chain(&self) -> Result<Vec<Vec<u8>>, Error> {
+        self.stream.get_ref().certificate_chain()
     }
 }

src/transport/smtp/client/async_net.rs

@@ -1,97 +1,99 @@
-#[cfg(any(
-    feature = "tokio02-rustls-tls",
-    feature = "tokio1-rustls-tls",
-    feature = "async-std1-rustls-tls"
-))]
-use std::sync::Arc;
 use std::{
-    net::SocketAddr,
+    fmt, io, mem,
+    net::{IpAddr, SocketAddr},
     pin::Pin,
     task::{Context, Poll},
+    time::Duration,
 };
 
-use futures_io::{AsyncRead as FuturesAsyncRead, AsyncWrite as FuturesAsyncWrite};
-use futures_io::{Error as IoError, ErrorKind, Result as IoResult};
-#[cfg(feature = "tokio02")]
-use tokio02_crate::io::{AsyncRead as _, AsyncWrite as _};
-#[cfg(feature = "tokio1")]
-use tokio1_crate::io::{AsyncRead as _, AsyncWrite as _, ReadBuf as Tokio1ReadBuf};
-
 #[cfg(feature = "async-std1")]
-use async_std::net::TcpStream as AsyncStd1TcpStream;
-#[cfg(feature = "tokio02")]
-use tokio02_crate::net::TcpStream as Tokio02TcpStream;
+use async_std::net::{TcpStream as AsyncStd1TcpStream, ToSocketAddrs as AsyncStd1ToSocketAddrs};
+use futures_io::{
+    AsyncRead as FuturesAsyncRead, AsyncWrite as FuturesAsyncWrite, Error as IoError, ErrorKind,
+    Result as IoResult,
+};
+#[cfg(feature = "async-std1-rustls")]
+use futures_rustls::client::TlsStream as AsyncStd1RustlsTlsStream;
+#[cfg(any(feature = "tokio1-rustls", feature = "async-std1-rustls"))]
+use rustls::pki_types::ServerName;
+#[cfg(feature = "tokio1-boring-tls")]
+use tokio1_boring::SslStream as Tokio1SslStream;
 #[cfg(feature = "tokio1")]
-use tokio1_crate::net::TcpStream as Tokio1TcpStream;
-
-#[cfg(feature = "async-std1-native-tls")]
-use async_native_tls::TlsStream as AsyncStd1TlsStream;
-#[cfg(feature = "tokio02-native-tls")]
-use tokio02_native_tls_crate::TlsStream as Tokio02TlsStream;
+use tokio1_crate::io::{AsyncRead, AsyncWrite, ReadBuf as Tokio1ReadBuf};
+#[cfg(feature = "tokio1")]
+use tokio1_crate::net::{
+    TcpSocket as Tokio1TcpSocket, TcpStream as Tokio1TcpStream,
+    ToSocketAddrs as Tokio1ToSocketAddrs,
+};
 #[cfg(feature = "tokio1-native-tls")]
 use tokio1_native_tls_crate::TlsStream as Tokio1TlsStream;
-
-#[cfg(feature = "async-std1-rustls-tls")]
-use async_rustls::client::TlsStream as AsyncStd1RustlsTlsStream;
-#[cfg(feature = "tokio02-rustls-tls")]
-use tokio02_rustls::client::TlsStream as Tokio02RustlsTlsStream;
-#[cfg(feature = "tokio1-rustls-tls")]
+#[cfg(feature = "tokio1-rustls")]
 use tokio1_rustls::client::TlsStream as Tokio1RustlsTlsStream;
 
 #[cfg(any(
-    feature = "tokio02-native-tls",
-    feature = "tokio02-rustls-tls",
     feature = "tokio1-native-tls",
-    feature = "tokio1-rustls-tls",
-    feature = "async-std1-native-tls",
-    feature = "async-std1-rustls-tls"
+    feature = "tokio1-rustls",
+    feature = "tokio1-boring-tls",
+    feature = "async-std1-rustls"
 ))]
 use super::InnerTlsParameters;
 use super::TlsParameters;
-use crate::transport::smtp::Error;
+#[cfg(feature = "tokio1")]
+use crate::transport::smtp::client::net::resolved_address_filter;
+use crate::transport::smtp::{error, Error};
 
 /// A network stream
+#[derive(Debug)]
+#[deprecated(
+    since = "0.11.14",
+    note = "This struct was not meant to be made public"
+)]
 pub struct AsyncNetworkStream {
     inner: InnerAsyncNetworkStream,
 }
 
+#[cfg(feature = "tokio1")]
+pub trait AsyncTokioStream: AsyncRead + AsyncWrite + Send + Sync + Unpin + fmt::Debug {
+    fn peer_addr(&self) -> io::Result<SocketAddr>;
+}
+
+#[cfg(feature = "tokio1")]
+impl AsyncTokioStream for Tokio1TcpStream {
+    fn peer_addr(&self) -> io::Result<SocketAddr> {
+        self.peer_addr()
+    }
+}
+
 /// Represents the different types of underlying network streams
 // usually only one TLS backend at a time is going to be enabled,
 // so clippy::large_enum_variant doesn't make sense here
 #[allow(clippy::large_enum_variant)]
 #[allow(dead_code)]
+#[derive(Debug)]
 enum InnerAsyncNetworkStream {
-    /// Plain Tokio 0.2 TCP stream
-    #[cfg(feature = "tokio02")]
-    Tokio02Tcp(Tokio02TcpStream),
-    /// Encrypted Tokio 0.2 TCP stream
-    #[cfg(feature = "tokio02-native-tls")]
-    Tokio02NativeTls(Tokio02TlsStream<Tokio02TcpStream>),
-    /// Encrypted Tokio 0.2 TCP stream
-    #[cfg(feature = "tokio02-rustls-tls")]
-    Tokio02RustlsTls(Tokio02RustlsTlsStream<Tokio02TcpStream>),
     /// Plain Tokio 1.x TCP stream
     #[cfg(feature = "tokio1")]
-    Tokio1Tcp(Tokio1TcpStream),
+    Tokio1Tcp(Box<dyn AsyncTokioStream>),
     /// Encrypted Tokio 1.x TCP stream
     #[cfg(feature = "tokio1-native-tls")]
-    Tokio1NativeTls(Tokio1TlsStream<Tokio1TcpStream>),
+    Tokio1NativeTls(Tokio1TlsStream<Box<dyn AsyncTokioStream>>),
     /// Encrypted Tokio 1.x TCP stream
-    #[cfg(feature = "tokio1-rustls-tls")]
-    Tokio1RustlsTls(Tokio1RustlsTlsStream<Tokio1TcpStream>),
+    #[cfg(feature = "tokio1-rustls")]
+    Tokio1RustlsTls(Tokio1RustlsTlsStream<Box<dyn AsyncTokioStream>>),
+    /// Encrypted Tokio 1.x TCP stream
+    #[cfg(feature = "tokio1-boring-tls")]
+    Tokio1BoringTls(Tokio1SslStream<Box<dyn AsyncTokioStream>>),
     /// Plain Tokio 1.x TCP stream
     #[cfg(feature = "async-std1")]
     AsyncStd1Tcp(AsyncStd1TcpStream),
     /// Encrypted Tokio 1.x TCP stream
-    #[cfg(feature = "async-std1-native-tls")]
-    AsyncStd1NativeTls(AsyncStd1TlsStream<AsyncStd1TcpStream>),
-    /// Encrypted Tokio 1.x TCP stream
-    #[cfg(feature = "async-std1-rustls-tls")]
+    #[cfg(feature = "async-std1-rustls")]
     AsyncStd1RustlsTls(AsyncStd1RustlsTlsStream<AsyncStd1TcpStream>),
     /// Can't be built
     None,
 }
 
+#[allow(deprecated)]
 impl AsyncNetworkStream {
     fn new(inner: InnerAsyncNetworkStream) -> Self {
         if let InnerAsyncNetworkStream::None = inner {
@@ -103,29 +105,21 @@ impl AsyncNetworkStream {
 
     /// Returns peer's address
     pub fn peer_addr(&self) -> IoResult<SocketAddr> {
-        match self.inner {
-            #[cfg(feature = "tokio02")]
-            InnerAsyncNetworkStream::Tokio02Tcp(ref s) => s.peer_addr(),
-            #[cfg(feature = "tokio02-native-tls")]
-            InnerAsyncNetworkStream::Tokio02NativeTls(ref s) => {
-                s.get_ref().get_ref().get_ref().peer_addr()
-            }
-            #[cfg(feature = "tokio02-rustls-tls")]
-            InnerAsyncNetworkStream::Tokio02RustlsTls(ref s) => s.get_ref().0.peer_addr(),
+        match &self.inner {
             #[cfg(feature = "tokio1")]
-            InnerAsyncNetworkStream::Tokio1Tcp(ref s) => s.peer_addr(),
+            InnerAsyncNetworkStream::Tokio1Tcp(s) => s.peer_addr(),
             #[cfg(feature = "tokio1-native-tls")]
-            InnerAsyncNetworkStream::Tokio1NativeTls(ref s) => {
+            InnerAsyncNetworkStream::Tokio1NativeTls(s) => {
                 s.get_ref().get_ref().get_ref().peer_addr()
             }
-            #[cfg(feature = "tokio1-rustls-tls")]
-            InnerAsyncNetworkStream::Tokio1RustlsTls(ref s) => s.get_ref().0.peer_addr(),
+            #[cfg(feature = "tokio1-rustls")]
+            InnerAsyncNetworkStream::Tokio1RustlsTls(s) => s.get_ref().0.peer_addr(),
+            #[cfg(feature = "tokio1-boring-tls")]
+            InnerAsyncNetworkStream::Tokio1BoringTls(s) => s.get_ref().peer_addr(),
             #[cfg(feature = "async-std1")]
-            InnerAsyncNetworkStream::AsyncStd1Tcp(ref s) => s.peer_addr(),
-            #[cfg(feature = "async-std1-native-tls")]
-            InnerAsyncNetworkStream::AsyncStd1NativeTls(ref s) => s.get_ref().peer_addr(),
-            #[cfg(feature = "async-std1-rustls-tls")]
-            InnerAsyncNetworkStream::AsyncStd1RustlsTls(ref s) => s.get_ref().0.peer_addr(),
+            InnerAsyncNetworkStream::AsyncStd1Tcp(s) => s.peer_addr(),
+            #[cfg(feature = "async-std1-rustls")]
+            InnerAsyncNetworkStream::AsyncStd1RustlsTls(s) => s.get_ref().0.peer_addr(),
             InnerAsyncNetworkStream::None => {
                 debug_assert!(false, "InnerAsyncNetworkStream::None must never be built");
                 Err(IoError::new(
@@ -136,30 +130,71 @@ impl AsyncNetworkStream {
         }
     }
 
-    #[cfg(feature = "tokio02")]
-    pub async fn connect_tokio02(
-        hostname: &str,
-        port: u16,
-        tls_parameters: Option<TlsParameters>,
-    ) -> Result<AsyncNetworkStream, Error> {
-        let tcp_stream = Tokio02TcpStream::connect((hostname, port)).await?;
-
-        let mut stream = AsyncNetworkStream::new(InnerAsyncNetworkStream::Tokio02Tcp(tcp_stream));
-        if let Some(tls_parameters) = tls_parameters {
-            stream.upgrade_tls(tls_parameters).await?;
-        }
-        Ok(stream)
+    #[cfg(feature = "tokio1")]
+    pub fn use_existing_tokio1(stream: Box<dyn AsyncTokioStream>) -> AsyncNetworkStream {
+        AsyncNetworkStream::new(InnerAsyncNetworkStream::Tokio1Tcp(stream))
     }
 
     #[cfg(feature = "tokio1")]
-    pub async fn connect_tokio1(
-        hostname: &str,
-        port: u16,
+    pub async fn connect_tokio1<T: Tokio1ToSocketAddrs>(
+        server: T,
+        timeout: Option<Duration>,
         tls_parameters: Option<TlsParameters>,
+        local_addr: Option<IpAddr>,
     ) -> Result<AsyncNetworkStream, Error> {
-        let tcp_stream = Tokio1TcpStream::connect((hostname, port)).await?;
+        async fn try_connect<T: Tokio1ToSocketAddrs>(
+            server: T,
+            timeout: Option<Duration>,
+            local_addr: Option<IpAddr>,
+        ) -> Result<Tokio1TcpStream, Error> {
+            let addrs = tokio1_crate::net::lookup_host(server)
+                .await
+                .map_err(error::connection)?
+                .filter(|resolved_addr| resolved_address_filter(resolved_addr, local_addr));
 
-        let mut stream = AsyncNetworkStream::new(InnerAsyncNetworkStream::Tokio1Tcp(tcp_stream));
+            let mut last_err = None;
+
+            for addr in addrs {
+                let socket = match addr.ip() {
+                    IpAddr::V4(_) => Tokio1TcpSocket::new_v4(),
+                    IpAddr::V6(_) => Tokio1TcpSocket::new_v6(),
+                }
+                .map_err(error::connection)?;
+                if let Some(local_addr) = local_addr {
+                    socket
+                        .bind(SocketAddr::new(local_addr, 0))
+                        .map_err(error::connection)?;
+                }
+
+                let connect_future = socket.connect(addr);
+                if let Some(timeout) = timeout {
+                    match tokio1_crate::time::timeout(timeout, connect_future).await {
+                        Ok(Ok(stream)) => return Ok(stream),
+                        Ok(Err(err)) => last_err = Some(err),
+                        Err(_) => {
+                            last_err = Some(io::Error::new(
+                                io::ErrorKind::TimedOut,
+                                "connection timed out",
+                            ));
+                        }
+                    }
+                } else {
+                    match connect_future.await {
+                        Ok(stream) => return Ok(stream),
+                        Err(err) => last_err = Some(err),
+                    }
+                }
+            }
+
+            Err(match last_err {
+                Some(last_err) => error::connection(last_err),
+                None => error::connection("could not resolve to any supported address"),
+            })
+        }
+
+        let tcp_stream = try_connect(server, timeout, local_addr).await?;
+        let mut stream =
+            AsyncNetworkStream::new(InnerAsyncNetworkStream::Tokio1Tcp(Box::new(tcp_stream)));
         if let Some(tls_parameters) = tls_parameters {
             stream.upgrade_tls(tls_parameters).await?;
         }
@@ -167,12 +202,48 @@ impl AsyncNetworkStream {
     }
 
     #[cfg(feature = "async-std1")]
-    pub async fn connect_asyncstd1(
-        hostname: &str,
-        port: u16,
+    pub async fn connect_asyncstd1<T: AsyncStd1ToSocketAddrs>(
+        server: T,
+        timeout: Option<Duration>,
         tls_parameters: Option<TlsParameters>,
     ) -> Result<AsyncNetworkStream, Error> {
-        let tcp_stream = AsyncStd1TcpStream::connect((hostname, port)).await?;
+        // Unfortunately, there doesn't currently seem to be a way to set the local address.
+        // Whilst we can create a AsyncStd1TcpStream from an existing socket, it needs to first have
+        // been connected, which is a blocking operation.
+        async fn try_connect_timeout<T: AsyncStd1ToSocketAddrs>(
+            server: T,
+            timeout: Duration,
+        ) -> Result<AsyncStd1TcpStream, Error> {
+            let addrs = server.to_socket_addrs().await.map_err(error::connection)?;
+
+            let mut last_err = None;
+
+            for addr in addrs {
+                let connect_future = AsyncStd1TcpStream::connect(&addr);
+                match async_std::future::timeout(timeout, connect_future).await {
+                    Ok(Ok(stream)) => return Ok(stream),
+                    Ok(Err(err)) => last_err = Some(err),
+                    Err(_) => {
+                        last_err = Some(io::Error::new(
+                            io::ErrorKind::TimedOut,
+                            "connection timed out",
+                        ));
+                    }
+                }
+            }
+
+            Err(match last_err {
+                Some(last_err) => error::connection(last_err),
+                None => error::connection("could not resolve to any address"),
+            })
+        }
+
+        let tcp_stream = match timeout {
+            Some(t) => try_connect_timeout(server, t).await?,
+            None => AsyncStd1TcpStream::connect(server)
+                .await
+                .map_err(error::connection)?,
+        };
 
         let mut stream = AsyncNetworkStream::new(InnerAsyncNetworkStream::AsyncStd1Tcp(tcp_stream));
         if let Some(tls_parameters) = tls_parameters {
@@ -183,67 +254,53 @@ impl AsyncNetworkStream {
 
     pub async fn upgrade_tls(&mut self, tls_parameters: TlsParameters) -> Result<(), Error> {
         match &self.inner {
-            #[cfg(all(
-                feature = "tokio02",
-                not(any(feature = "tokio02-native-tls", feature = "tokio02-rustls-tls"))
-            ))]
-            InnerAsyncNetworkStream::Tokio02Tcp(_) => {
-                let _ = tls_parameters;
-                panic!("Trying to upgrade an AsyncNetworkStream without having enabled either the tokio02-native-tls or the tokio02-rustls-tls feature");
-            }
-
-            #[cfg(any(feature = "tokio02-native-tls", feature = "tokio02-rustls-tls"))]
-            InnerAsyncNetworkStream::Tokio02Tcp(_) => {
-                // get owned TcpStream
-                let tcp_stream = std::mem::replace(&mut self.inner, InnerAsyncNetworkStream::None);
-                let tcp_stream = match tcp_stream {
-                    InnerAsyncNetworkStream::Tokio02Tcp(tcp_stream) => tcp_stream,
-                    _ => unreachable!(),
-                };
-
-                self.inner = Self::upgrade_tokio02_tls(tcp_stream, tls_parameters).await?;
-                Ok(())
-            }
             #[cfg(all(
                 feature = "tokio1",
-                not(any(feature = "tokio1-native-tls", feature = "tokio1-rustls-tls"))
+                not(any(
+                    feature = "tokio1-native-tls",
+                    feature = "tokio1-rustls",
+                    feature = "tokio1-boring-tls"
+                ))
             ))]
             InnerAsyncNetworkStream::Tokio1Tcp(_) => {
                 let _ = tls_parameters;
-                panic!("Trying to upgrade an AsyncNetworkStream without having enabled either the tokio1-native-tls or the tokio1-rustls-tls feature");
+                panic!("Trying to upgrade an AsyncNetworkStream without having enabled either the tokio1-native-tls or the tokio1-rustls feature");
             }
 
-            #[cfg(any(feature = "tokio1-native-tls", feature = "tokio1-rustls-tls"))]
+            #[cfg(any(
+                feature = "tokio1-native-tls",
+                feature = "tokio1-rustls",
+                feature = "tokio1-boring-tls"
+            ))]
             InnerAsyncNetworkStream::Tokio1Tcp(_) => {
                 // get owned TcpStream
-                let tcp_stream = std::mem::replace(&mut self.inner, InnerAsyncNetworkStream::None);
-                let tcp_stream = match tcp_stream {
-                    InnerAsyncNetworkStream::Tokio1Tcp(tcp_stream) => tcp_stream,
-                    _ => unreachable!(),
+                let tcp_stream = mem::replace(&mut self.inner, InnerAsyncNetworkStream::None);
+                let InnerAsyncNetworkStream::Tokio1Tcp(tcp_stream) = tcp_stream else {
+                    unreachable!()
                 };
 
-                self.inner = Self::upgrade_tokio1_tls(tcp_stream, tls_parameters).await?;
+                self.inner = Self::upgrade_tokio1_tls(tcp_stream, tls_parameters)
+                    .await
+                    .map_err(error::connection)?;
                 Ok(())
             }
-            #[cfg(all(
-                feature = "async-std1",
-                not(any(feature = "async-std1-native-tls", feature = "async-std1-rustls-tls"))
-            ))]
+            #[cfg(all(feature = "async-std1", not(feature = "async-std1-rustls")))]
             InnerAsyncNetworkStream::AsyncStd1Tcp(_) => {
                 let _ = tls_parameters;
-                panic!("Trying to upgrade an AsyncNetworkStream without having enabled either the async-std1-native-tls or the async-std1-rustls-tls feature");
+                panic!("Trying to upgrade an AsyncNetworkStream without having enabled the async-std1-rustls feature");
             }
 
-            #[cfg(any(feature = "async-std1-native-tls", feature = "async-std1-rustls-tls"))]
+            #[cfg(feature = "async-std1-rustls")]
             InnerAsyncNetworkStream::AsyncStd1Tcp(_) => {
                 // get owned TcpStream
-                let tcp_stream = std::mem::replace(&mut self.inner, InnerAsyncNetworkStream::None);
-                let tcp_stream = match tcp_stream {
-                    InnerAsyncNetworkStream::AsyncStd1Tcp(tcp_stream) => tcp_stream,
-                    _ => unreachable!(),
+                let tcp_stream = mem::replace(&mut self.inner, InnerAsyncNetworkStream::None);
+                let InnerAsyncNetworkStream::AsyncStd1Tcp(tcp_stream) = tcp_stream else {
+                    unreachable!()
                 };
 
-                self.inner = Self::upgrade_asyncstd1_tls(tcp_stream, tls_parameters).await?;
+                self.inner = Self::upgrade_asyncstd1_tls(tcp_stream, tls_parameters)
+                    .await
+                    .map_err(error::connection)?;
                 Ok(())
             }
             _ => Ok(()),
@@ -251,54 +308,16 @@ impl AsyncNetworkStream {
     }
 
     #[allow(unused_variables)]
-    #[cfg(any(feature = "tokio02-native-tls", feature = "tokio02-rustls-tls"))]
-    async fn upgrade_tokio02_tls(
-        tcp_stream: Tokio02TcpStream,
-        mut tls_parameters: TlsParameters,
-    ) -> Result<InnerAsyncNetworkStream, Error> {
-        let domain = std::mem::take(&mut tls_parameters.domain);
-
-        match tls_parameters.connector {
-            #[cfg(feature = "native-tls")]
-            InnerTlsParameters::NativeTls(connector) => {
-                #[cfg(not(feature = "tokio02-native-tls"))]
-                panic!("built without the tokio02-native-tls feature");
-
-                #[cfg(feature = "tokio02-native-tls")]
-                return {
-                    use tokio02_native_tls_crate::TlsConnector;
-
-                    let connector = TlsConnector::from(connector);
-                    let stream = connector.connect(&domain, tcp_stream).await?;
-                    Ok(InnerAsyncNetworkStream::Tokio02NativeTls(stream))
-                };
-            }
-            #[cfg(feature = "rustls-tls")]
-            InnerTlsParameters::RustlsTls(config) => {
-                #[cfg(not(feature = "tokio02-rustls-tls"))]
-                panic!("built without the tokio02-rustls-tls feature");
-
-                #[cfg(feature = "tokio02-rustls-tls")]
-                return {
-                    use tokio02_rustls::{webpki::DNSNameRef, TlsConnector};
-
-                    let domain = DNSNameRef::try_from_ascii_str(&domain)?;
-
-                    let connector = TlsConnector::from(Arc::new(config));
-                    let stream = connector.connect(domain, tcp_stream).await?;
-                    Ok(InnerAsyncNetworkStream::Tokio02RustlsTls(stream))
-                };
-            }
-        }
-    }
-
-    #[allow(unused_variables)]
-    #[cfg(any(feature = "tokio1-native-tls", feature = "tokio1-rustls-tls"))]
+    #[cfg(any(
+        feature = "tokio1-native-tls",
+        feature = "tokio1-rustls",
+        feature = "tokio1-boring-tls"
+    ))]
     async fn upgrade_tokio1_tls(
-        tcp_stream: Tokio1TcpStream,
-        mut tls_parameters: TlsParameters,
+        tcp_stream: Box<dyn AsyncTokioStream>,
+        tls_parameters: TlsParameters,
     ) -> Result<InnerAsyncNetworkStream, Error> {
-        let domain = std::mem::take(&mut tls_parameters.domain);
+        let domain = tls_parameters.domain().to_owned();
 
         match tls_parameters.connector {
             #[cfg(feature = "native-tls")]
@@ -311,118 +330,234 @@ impl AsyncNetworkStream {
                     use tokio1_native_tls_crate::TlsConnector;
 
                     let connector = TlsConnector::from(connector);
-                    let stream = connector.connect(&domain, tcp_stream).await?;
+                    let stream = connector
+                        .connect(&domain, tcp_stream)
+                        .await
+                        .map_err(error::connection)?;
                     Ok(InnerAsyncNetworkStream::Tokio1NativeTls(stream))
                 };
             }
-            #[cfg(feature = "rustls-tls")]
+            #[cfg(feature = "rustls")]
             InnerTlsParameters::RustlsTls(config) => {
-                #[cfg(not(feature = "tokio1-rustls-tls"))]
-                panic!("built without the tokio1-rustls-tls feature");
+                #[cfg(not(feature = "tokio1-rustls"))]
+                panic!("built without the tokio1-rustls feature");
 
-                #[cfg(feature = "tokio1-rustls-tls")]
+                #[cfg(feature = "tokio1-rustls")]
                 return {
-                    use tokio1_rustls::{webpki::DNSNameRef, TlsConnector};
+                    use tokio1_rustls::TlsConnector;
 
-                    let domain = DNSNameRef::try_from_ascii_str(&domain)?;
+                    let domain = ServerName::try_from(domain.as_str())
+                        .map_err(|_| error::connection("domain isn't a valid DNS name"))?;
 
-                    let connector = TlsConnector::from(Arc::new(config));
-                    let stream = connector.connect(domain, tcp_stream).await?;
+                    let connector = TlsConnector::from(config);
+                    let stream = connector
+                        .connect(domain.to_owned(), tcp_stream)
+                        .await
+                        .map_err(error::connection)?;
                     Ok(InnerAsyncNetworkStream::Tokio1RustlsTls(stream))
                 };
             }
+            #[cfg(feature = "boring-tls")]
+            InnerTlsParameters::BoringTls(connector) => {
+                #[cfg(not(feature = "tokio1-boring-tls"))]
+                panic!("built without the tokio1-boring-tls feature");
+
+                #[cfg(feature = "tokio1-boring-tls")]
+                return {
+                    let mut config = connector.configure().map_err(error::connection)?;
+                    config.set_verify_hostname(tls_parameters.accept_invalid_hostnames);
+
+                    let stream = tokio1_boring::connect(config, &domain, tcp_stream)
+                        .await
+                        .map_err(error::connection)?;
+                    Ok(InnerAsyncNetworkStream::Tokio1BoringTls(stream))
+                };
+            }
         }
     }
 
     #[allow(unused_variables)]
-    #[cfg(any(feature = "async-std1-native-tls", feature = "async-std1-rustls-tls"))]
+    #[cfg(feature = "async-std1-rustls")]
     async fn upgrade_asyncstd1_tls(
         tcp_stream: AsyncStd1TcpStream,
         mut tls_parameters: TlsParameters,
     ) -> Result<InnerAsyncNetworkStream, Error> {
-        let domain = std::mem::take(&mut tls_parameters.domain);
+        let domain = mem::take(&mut tls_parameters.domain);
 
         match tls_parameters.connector {
             #[cfg(feature = "native-tls")]
             InnerTlsParameters::NativeTls(connector) => {
                 panic!("native-tls isn't supported with async-std yet. See https://github.com/lettre/lettre/pull/531#issuecomment-757893531");
-
-                /*
-                #[cfg(not(feature = "async-std1-native-tls"))]
-                panic!("built without the async-std1-native-tls feature");
-
-                #[cfg(feature = "async-std1-native-tls")]
-                return {
-                    use async_native_tls::TlsConnector;
-
-                    // TODO: fix
-                    let connector: TlsConnector = todo!();
-                    // let connector = TlsConnector::from(connector);
-                    let stream = connector.connect(&domain, tcp_stream).await?;
-                    Ok(InnerAsyncNetworkStream::AsyncStd1NativeTls(stream))
-                };
-                */
             }
-            #[cfg(feature = "rustls-tls")]
+            #[cfg(feature = "rustls")]
             InnerTlsParameters::RustlsTls(config) => {
-                #[cfg(not(feature = "async-std1-rustls-tls"))]
-                panic!("built without the async-std1-rustls-tls feature");
+                #[cfg(not(feature = "async-std1-rustls"))]
+                panic!("built without the async-std1-rustls feature");
 
-                #[cfg(feature = "async-std1-rustls-tls")]
+                #[cfg(feature = "async-std1-rustls")]
                 return {
-                    use async_rustls::webpki::DNSNameRef;
-                    use async_rustls::TlsConnector;
+                    use futures_rustls::TlsConnector;
 
-                    let domain = DNSNameRef::try_from_ascii_str(&domain)?;
+                    let domain = ServerName::try_from(domain.as_str())
+                        .map_err(|_| error::connection("domain isn't a valid DNS name"))?;
 
-                    let connector = TlsConnector::from(Arc::new(config));
-                    let stream = connector.connect(domain, tcp_stream).await?;
+                    let connector = TlsConnector::from(config);
+                    let stream = connector
+                        .connect(domain.to_owned(), tcp_stream)
+                        .await
+                        .map_err(error::connection)?;
                     Ok(InnerAsyncNetworkStream::AsyncStd1RustlsTls(stream))
                 };
             }
+            #[cfg(feature = "boring-tls")]
+            InnerTlsParameters::BoringTls(connector) => {
+                panic!("boring-tls isn't supported with async-std yet.");
+            }
         }
     }
 
     pub fn is_encrypted(&self) -> bool {
-        match self.inner {
-            #[cfg(feature = "tokio02")]
-            InnerAsyncNetworkStream::Tokio02Tcp(_) => false,
-            #[cfg(feature = "tokio02-native-tls")]
-            InnerAsyncNetworkStream::Tokio02NativeTls(_) => true,
-            #[cfg(feature = "tokio02-rustls-tls")]
-            InnerAsyncNetworkStream::Tokio02RustlsTls(_) => true,
+        match &self.inner {
             #[cfg(feature = "tokio1")]
             InnerAsyncNetworkStream::Tokio1Tcp(_) => false,
             #[cfg(feature = "tokio1-native-tls")]
             InnerAsyncNetworkStream::Tokio1NativeTls(_) => true,
-            #[cfg(feature = "tokio1-rustls-tls")]
+            #[cfg(feature = "tokio1-rustls")]
             InnerAsyncNetworkStream::Tokio1RustlsTls(_) => true,
+            #[cfg(feature = "tokio1-boring-tls")]
+            InnerAsyncNetworkStream::Tokio1BoringTls(_) => true,
             #[cfg(feature = "async-std1")]
             InnerAsyncNetworkStream::AsyncStd1Tcp(_) => false,
-            #[cfg(feature = "async-std1-native-tls")]
-            InnerAsyncNetworkStream::AsyncStd1NativeTls(_) => true,
-            #[cfg(feature = "async-std1-rustls-tls")]
+            #[cfg(feature = "async-std1-rustls")]
             InnerAsyncNetworkStream::AsyncStd1RustlsTls(_) => true,
             InnerAsyncNetworkStream::None => false,
         }
     }
+
+    #[cfg(feature = "boring-tls")]
+    pub fn tls_verify_result(&self) -> Result<(), Error> {
+        match &self.inner {
+            #[cfg(feature = "tokio1")]
+            InnerAsyncNetworkStream::Tokio1Tcp(_) => {
+                Err(error::client("Connection is not encrypted"))
+            }
+            #[cfg(feature = "tokio1-native-tls")]
+            InnerAsyncNetworkStream::Tokio1NativeTls(_) => panic!("Unsupported"),
+            #[cfg(feature = "tokio1-rustls")]
+            InnerAsyncNetworkStream::Tokio1RustlsTls(_) => panic!("Unsupported"),
+            #[cfg(feature = "tokio1-boring-tls")]
+            InnerAsyncNetworkStream::Tokio1BoringTls(stream) => {
+                stream.ssl().verify_result().map_err(error::tls)
+            }
+            #[cfg(feature = "async-std1")]
+            InnerAsyncNetworkStream::AsyncStd1Tcp(_) => {
+                Err(error::client("Connection is not encrypted"))
+            }
+            #[cfg(feature = "async-std1-rustls")]
+            InnerAsyncNetworkStream::AsyncStd1RustlsTls(_) => panic!("Unsupported"),
+            InnerAsyncNetworkStream::None => panic!("InnerNetworkStream::None must never be built"),
+        }
+    }
+    pub fn certificate_chain(&self) -> Result<Vec<Vec<u8>>, Error> {
+        match &self.inner {
+            #[cfg(feature = "tokio1")]
+            InnerAsyncNetworkStream::Tokio1Tcp(_) => {
+                Err(error::client("Connection is not encrypted"))
+            }
+            #[cfg(feature = "tokio1-native-tls")]
+            InnerAsyncNetworkStream::Tokio1NativeTls(_) => panic!("Unsupported"),
+            #[cfg(feature = "tokio1-rustls")]
+            InnerAsyncNetworkStream::Tokio1RustlsTls(stream) => Ok(stream
+                .get_ref()
+                .1
+                .peer_certificates()
+                .unwrap()
+                .iter()
+                .map(|c| c.to_vec())
+                .collect()),
+            #[cfg(feature = "tokio1-boring-tls")]
+            InnerAsyncNetworkStream::Tokio1BoringTls(stream) => Ok(stream
+                .ssl()
+                .peer_cert_chain()
+                .unwrap()
+                .iter()
+                .map(|c| c.to_der().map_err(error::tls))
+                .collect::<Result<Vec<_>, _>>()?),
+            #[cfg(feature = "async-std1")]
+            InnerAsyncNetworkStream::AsyncStd1Tcp(_) => {
+                Err(error::client("Connection is not encrypted"))
+            }
+            #[cfg(feature = "async-std1-rustls")]
+            InnerAsyncNetworkStream::AsyncStd1RustlsTls(stream) => Ok(stream
+                .get_ref()
+                .1
+                .peer_certificates()
+                .unwrap()
+                .iter()
+                .map(|c| c.to_vec())
+                .collect()),
+            InnerAsyncNetworkStream::None => panic!("InnerNetworkStream::None must never be built"),
+        }
+    }
+
+    pub fn peer_certificate(&self) -> Result<Vec<u8>, Error> {
+        match &self.inner {
+            #[cfg(feature = "tokio1")]
+            InnerAsyncNetworkStream::Tokio1Tcp(_) => {
+                Err(error::client("Connection is not encrypted"))
+            }
+            #[cfg(feature = "tokio1-native-tls")]
+            InnerAsyncNetworkStream::Tokio1NativeTls(stream) => Ok(stream
+                .get_ref()
+                .peer_certificate()
+                .map_err(error::tls)?
+                .unwrap()
+                .to_der()
+                .map_err(error::tls)?),
+            #[cfg(feature = "tokio1-rustls")]
+            InnerAsyncNetworkStream::Tokio1RustlsTls(stream) => Ok(stream
+                .get_ref()
+                .1
+                .peer_certificates()
+                .unwrap()
+                .first()
+                .unwrap()
+                .to_vec()),
+            #[cfg(feature = "tokio1-boring-tls")]
+            InnerAsyncNetworkStream::Tokio1BoringTls(stream) => Ok(stream
+                .ssl()
+                .peer_certificate()
+                .unwrap()
+                .to_der()
+                .map_err(error::tls)?),
+            #[cfg(feature = "async-std1")]
+            InnerAsyncNetworkStream::AsyncStd1Tcp(_) => {
+                Err(error::client("Connection is not encrypted"))
+            }
+            #[cfg(feature = "async-std1-rustls")]
+            InnerAsyncNetworkStream::AsyncStd1RustlsTls(stream) => Ok(stream
+                .get_ref()
+                .1
+                .peer_certificates()
+                .unwrap()
+                .first()
+                .unwrap()
+                .to_vec()),
+            InnerAsyncNetworkStream::None => panic!("InnerNetworkStream::None must never be built"),
+        }
+    }
 }
 
+#[allow(deprecated)]
 impl FuturesAsyncRead for AsyncNetworkStream {
     fn poll_read(
         mut self: Pin<&mut Self>,
         cx: &mut Context<'_>,
         buf: &mut [u8],
     ) -> Poll<IoResult<usize>> {
-        match self.inner {
-            #[cfg(feature = "tokio02")]
-            InnerAsyncNetworkStream::Tokio02Tcp(ref mut s) => Pin::new(s).poll_read(cx, buf),
-            #[cfg(feature = "tokio02-native-tls")]
-            InnerAsyncNetworkStream::Tokio02NativeTls(ref mut s) => Pin::new(s).poll_read(cx, buf),
-            #[cfg(feature = "tokio02-rustls-tls")]
-            InnerAsyncNetworkStream::Tokio02RustlsTls(ref mut s) => Pin::new(s).poll_read(cx, buf),
+        match &mut self.inner {
             #[cfg(feature = "tokio1")]
-            InnerAsyncNetworkStream::Tokio1Tcp(ref mut s) => {
+            InnerAsyncNetworkStream::Tokio1Tcp(s) => {
                 let mut b = Tokio1ReadBuf::new(buf);
                 match Pin::new(s).poll_read(cx, &mut b) {
                     Poll::Ready(Ok(())) => Poll::Ready(Ok(b.filled().len())),
@@ -431,7 +566,7 @@ impl FuturesAsyncRead for AsyncNetworkStream {
                 }
             }
             #[cfg(feature = "tokio1-native-tls")]
-            InnerAsyncNetworkStream::Tokio1NativeTls(ref mut s) => {
+            InnerAsyncNetworkStream::Tokio1NativeTls(s) => {
                 let mut b = Tokio1ReadBuf::new(buf);
                 match Pin::new(s).poll_read(cx, &mut b) {
                     Poll::Ready(Ok(())) => Poll::Ready(Ok(b.filled().len())),
@@ -439,8 +574,17 @@ impl FuturesAsyncRead for AsyncNetworkStream {
                     Poll::Pending => Poll::Pending,
                 }
             }
-            #[cfg(feature = "tokio1-rustls-tls")]
-            InnerAsyncNetworkStream::Tokio1RustlsTls(ref mut s) => {
+            #[cfg(feature = "tokio1-rustls")]
+            InnerAsyncNetworkStream::Tokio1RustlsTls(s) => {
+                let mut b = Tokio1ReadBuf::new(buf);
+                match Pin::new(s).poll_read(cx, &mut b) {
+                    Poll::Ready(Ok(())) => Poll::Ready(Ok(b.filled().len())),
+                    Poll::Ready(Err(err)) => Poll::Ready(Err(err)),
+                    Poll::Pending => Poll::Pending,
+                }
+            }
+            #[cfg(feature = "tokio1-boring-tls")]
+            InnerAsyncNetworkStream::Tokio1BoringTls(s) => {
                 let mut b = Tokio1ReadBuf::new(buf);
                 match Pin::new(s).poll_read(cx, &mut b) {
                     Poll::Ready(Ok(())) => Poll::Ready(Ok(b.filled().len())),
@@ -449,15 +593,9 @@ impl FuturesAsyncRead for AsyncNetworkStream {
                 }
             }
             #[cfg(feature = "async-std1")]
-            InnerAsyncNetworkStream::AsyncStd1Tcp(ref mut s) => Pin::new(s).poll_read(cx, buf),
-            #[cfg(feature = "async-std1-native-tls")]
-            InnerAsyncNetworkStream::AsyncStd1NativeTls(ref mut s) => {
-                Pin::new(s).poll_read(cx, buf)
-            }
-            #[cfg(feature = "async-std1-rustls-tls")]
-            InnerAsyncNetworkStream::AsyncStd1RustlsTls(ref mut s) => {
-                Pin::new(s).poll_read(cx, buf)
-            }
+            InnerAsyncNetworkStream::AsyncStd1Tcp(s) => Pin::new(s).poll_read(cx, buf),
+            #[cfg(feature = "async-std1-rustls")]
+            InnerAsyncNetworkStream::AsyncStd1RustlsTls(s) => Pin::new(s).poll_read(cx, buf),
             InnerAsyncNetworkStream::None => {
                 debug_assert!(false, "InnerAsyncNetworkStream::None must never be built");
                 Poll::Ready(Ok(0))
@@ -466,35 +604,26 @@ impl FuturesAsyncRead for AsyncNetworkStream {
     }
 }
 
+#[allow(deprecated)]
 impl FuturesAsyncWrite for AsyncNetworkStream {
     fn poll_write(
         mut self: Pin<&mut Self>,
         cx: &mut Context<'_>,
         buf: &[u8],
     ) -> Poll<IoResult<usize>> {
-        match self.inner {
-            #[cfg(feature = "tokio02")]
-            InnerAsyncNetworkStream::Tokio02Tcp(ref mut s) => Pin::new(s).poll_write(cx, buf),
-            #[cfg(feature = "tokio02-native-tls")]
-            InnerAsyncNetworkStream::Tokio02NativeTls(ref mut s) => Pin::new(s).poll_write(cx, buf),
-            #[cfg(feature = "tokio02-rustls-tls")]
-            InnerAsyncNetworkStream::Tokio02RustlsTls(ref mut s) => Pin::new(s).poll_write(cx, buf),
+        match &mut self.inner {
             #[cfg(feature = "tokio1")]
-            InnerAsyncNetworkStream::Tokio1Tcp(ref mut s) => Pin::new(s).poll_write(cx, buf),
+            InnerAsyncNetworkStream::Tokio1Tcp(s) => Pin::new(s).poll_write(cx, buf),
             #[cfg(feature = "tokio1-native-tls")]
-            InnerAsyncNetworkStream::Tokio1NativeTls(ref mut s) => Pin::new(s).poll_write(cx, buf),
-            #[cfg(feature = "tokio1-rustls-tls")]
-            InnerAsyncNetworkStream::Tokio1RustlsTls(ref mut s) => Pin::new(s).poll_write(cx, buf),
+            InnerAsyncNetworkStream::Tokio1NativeTls(s) => Pin::new(s).poll_write(cx, buf),
+            #[cfg(feature = "tokio1-rustls")]
+            InnerAsyncNetworkStream::Tokio1RustlsTls(s) => Pin::new(s).poll_write(cx, buf),
+            #[cfg(feature = "tokio1-boring-tls")]
+            InnerAsyncNetworkStream::Tokio1BoringTls(s) => Pin::new(s).poll_write(cx, buf),
             #[cfg(feature = "async-std1")]
-            InnerAsyncNetworkStream::AsyncStd1Tcp(ref mut s) => Pin::new(s).poll_write(cx, buf),
-            #[cfg(feature = "async-std1-native-tls")]
-            InnerAsyncNetworkStream::AsyncStd1NativeTls(ref mut s) => {
-                Pin::new(s).poll_write(cx, buf)
-            }
-            #[cfg(feature = "async-std1-rustls-tls")]
-            InnerAsyncNetworkStream::AsyncStd1RustlsTls(ref mut s) => {
-                Pin::new(s).poll_write(cx, buf)
-            }
+            InnerAsyncNetworkStream::AsyncStd1Tcp(s) => Pin::new(s).poll_write(cx, buf),
+            #[cfg(feature = "async-std1-rustls")]
+            InnerAsyncNetworkStream::AsyncStd1RustlsTls(s) => Pin::new(s).poll_write(cx, buf),
             InnerAsyncNetworkStream::None => {
                 debug_assert!(false, "InnerAsyncNetworkStream::None must never be built");
                 Poll::Ready(Ok(0))
@@ -503,25 +632,19 @@ impl FuturesAsyncWrite for AsyncNetworkStream {
     }
 
     fn poll_flush(mut self: Pin<&mut Self>, cx: &mut Context<'_>) -> Poll<IoResult<()>> {
-        match self.inner {
-            #[cfg(feature = "tokio02")]
-            InnerAsyncNetworkStream::Tokio02Tcp(ref mut s) => Pin::new(s).poll_flush(cx),
-            #[cfg(feature = "tokio02-native-tls")]
-            InnerAsyncNetworkStream::Tokio02NativeTls(ref mut s) => Pin::new(s).poll_flush(cx),
-            #[cfg(feature = "tokio02-rustls-tls")]
-            InnerAsyncNetworkStream::Tokio02RustlsTls(ref mut s) => Pin::new(s).poll_flush(cx),
+        match &mut self.inner {
             #[cfg(feature = "tokio1")]
-            InnerAsyncNetworkStream::Tokio1Tcp(ref mut s) => Pin::new(s).poll_flush(cx),
+            InnerAsyncNetworkStream::Tokio1Tcp(s) => Pin::new(s).poll_flush(cx),
             #[cfg(feature = "tokio1-native-tls")]
-            InnerAsyncNetworkStream::Tokio1NativeTls(ref mut s) => Pin::new(s).poll_flush(cx),
-            #[cfg(feature = "tokio1-rustls-tls")]
-            InnerAsyncNetworkStream::Tokio1RustlsTls(ref mut s) => Pin::new(s).poll_flush(cx),
+            InnerAsyncNetworkStream::Tokio1NativeTls(s) => Pin::new(s).poll_flush(cx),
+            #[cfg(feature = "tokio1-rustls")]
+            InnerAsyncNetworkStream::Tokio1RustlsTls(s) => Pin::new(s).poll_flush(cx),
+            #[cfg(feature = "tokio1-boring-tls")]
+            InnerAsyncNetworkStream::Tokio1BoringTls(s) => Pin::new(s).poll_flush(cx),
             #[cfg(feature = "async-std1")]
-            InnerAsyncNetworkStream::AsyncStd1Tcp(ref mut s) => Pin::new(s).poll_flush(cx),
-            #[cfg(feature = "async-std1-native-tls")]
-            InnerAsyncNetworkStream::AsyncStd1NativeTls(ref mut s) => Pin::new(s).poll_flush(cx),
-            #[cfg(feature = "async-std1-rustls-tls")]
-            InnerAsyncNetworkStream::AsyncStd1RustlsTls(ref mut s) => Pin::new(s).poll_flush(cx),
+            InnerAsyncNetworkStream::AsyncStd1Tcp(s) => Pin::new(s).poll_flush(cx),
+            #[cfg(feature = "async-std1-rustls")]
+            InnerAsyncNetworkStream::AsyncStd1RustlsTls(s) => Pin::new(s).poll_flush(cx),
             InnerAsyncNetworkStream::None => {
                 debug_assert!(false, "InnerAsyncNetworkStream::None must never be built");
                 Poll::Ready(Ok(()))
@@ -530,25 +653,19 @@ impl FuturesAsyncWrite for AsyncNetworkStream {
     }
 
     fn poll_close(mut self: Pin<&mut Self>, cx: &mut Context<'_>) -> Poll<IoResult<()>> {
-        match self.inner {
-            #[cfg(feature = "tokio02")]
-            InnerAsyncNetworkStream::Tokio02Tcp(ref mut s) => Pin::new(s).poll_shutdown(cx),
-            #[cfg(feature = "tokio02-native-tls")]
-            InnerAsyncNetworkStream::Tokio02NativeTls(ref mut s) => Pin::new(s).poll_shutdown(cx),
-            #[cfg(feature = "tokio02-rustls-tls")]
-            InnerAsyncNetworkStream::Tokio02RustlsTls(ref mut s) => Pin::new(s).poll_shutdown(cx),
+        match &mut self.inner {
             #[cfg(feature = "tokio1")]
-            InnerAsyncNetworkStream::Tokio1Tcp(ref mut s) => Pin::new(s).poll_shutdown(cx),
+            InnerAsyncNetworkStream::Tokio1Tcp(s) => Pin::new(s).poll_shutdown(cx),
             #[cfg(feature = "tokio1-native-tls")]
-            InnerAsyncNetworkStream::Tokio1NativeTls(ref mut s) => Pin::new(s).poll_shutdown(cx),
-            #[cfg(feature = "tokio1-rustls-tls")]
-            InnerAsyncNetworkStream::Tokio1RustlsTls(ref mut s) => Pin::new(s).poll_shutdown(cx),
+            InnerAsyncNetworkStream::Tokio1NativeTls(s) => Pin::new(s).poll_shutdown(cx),
+            #[cfg(feature = "tokio1-rustls")]
+            InnerAsyncNetworkStream::Tokio1RustlsTls(s) => Pin::new(s).poll_shutdown(cx),
+            #[cfg(feature = "tokio1-boring-tls")]
+            InnerAsyncNetworkStream::Tokio1BoringTls(s) => Pin::new(s).poll_shutdown(cx),
             #[cfg(feature = "async-std1")]
-            InnerAsyncNetworkStream::AsyncStd1Tcp(ref mut s) => Pin::new(s).poll_close(cx),
-            #[cfg(feature = "async-std1-native-tls")]
-            InnerAsyncNetworkStream::AsyncStd1NativeTls(ref mut s) => Pin::new(s).poll_close(cx),
-            #[cfg(feature = "async-std1-rustls-tls")]
-            InnerAsyncNetworkStream::AsyncStd1RustlsTls(ref mut s) => Pin::new(s).poll_close(cx),
+            InnerAsyncNetworkStream::AsyncStd1Tcp(s) => Pin::new(s).poll_close(cx),
+            #[cfg(feature = "async-std1-rustls")]
+            InnerAsyncNetworkStream::AsyncStd1RustlsTls(s) => Pin::new(s).poll_close(cx),
             InnerAsyncNetworkStream::None => {
                 debug_assert!(false, "InnerAsyncNetworkStream::None must never be built");
                 Poll::Ready(Ok(()))

src/transport/smtp/client/connection.rs

@@ -1,22 +1,24 @@
 use std::{
     fmt::Display,
     io::{self, BufRead, BufReader, Write},
-    net::ToSocketAddrs,
+    net::{IpAddr, ToSocketAddrs},
     time::Duration,
 };
 
-use super::{ClientCodec, NetworkStream, TlsParameters};
-use crate::address::Envelope;
-use crate::transport::smtp::{
-    authentication::{Credentials, Mechanism},
-    commands::*,
-    error::Error,
-    extension::{ClientId, Extension, MailBodyParameter, MailParameter, ServerInfo},
-    response::{parse_response, Response},
-};
-
 #[cfg(feature = "tracing")]
 use super::escape_crlf;
+use super::{ClientCodec, NetworkStream, TlsParameters};
+use crate::{
+    address::Envelope,
+    transport::smtp::{
+        authentication::{Credentials, Mechanism},
+        commands::{Auth, Data, Ehlo, Mail, Noop, Quit, Rcpt, Starttls},
+        error,
+        error::Error,
+        extension::{ClientId, Extension, MailBodyParameter, MailParameter, ServerInfo},
+        response::{parse_response, Response},
+    },
+};
 
 macro_rules! try_smtp (
     ($err: expr, $client: ident) => ({
@@ -42,6 +44,7 @@ pub struct SmtpConnection {
 }
 
 impl SmtpConnection {
+    /// Get information about the server
     pub fn server_info(&self) -> &ServerInfo {
         &self.server_info
     }
@@ -56,15 +59,16 @@ impl SmtpConnection {
         timeout: Option<Duration>,
         hello_name: &ClientId,
         tls_parameters: Option<&TlsParameters>,
+        local_address: Option<IpAddr>,
     ) -> Result<SmtpConnection, Error> {
-        let stream = NetworkStream::connect(server, timeout, tls_parameters)?;
+        let stream = NetworkStream::connect(server, timeout, tls_parameters, local_address)?;
         let stream = BufReader::new(stream);
         let mut conn = SmtpConnection {
             stream,
             panic: false,
             server_info: ServerInfo::default(),
         };
-        conn.set_timeout(timeout)?;
+        conn.set_timeout(timeout).map_err(error::network)?;
         // TODO log
         let _response = conn.read_response()?;
 
@@ -80,9 +84,32 @@ impl SmtpConnection {
         // Mail
         let mut mail_options = vec![];
 
-        if self.server_info().supports_feature(Extension::EightBitMime) {
+        // Internationalization handling
+        //
+        // * 8BITMIME: https://tools.ietf.org/html/rfc6152
+        // * SMTPUTF8: https://tools.ietf.org/html/rfc653
+
+        // Check for non-ascii addresses and use the SMTPUTF8 option if any.
+        if envelope.has_non_ascii_addresses() {
+            if !self.server_info().supports_feature(Extension::SmtpUtfEight) {
+                // don't try to send non-ascii addresses (per RFC)
+                return Err(error::client(
+                    "Envelope contains non-ascii chars but server does not support SMTPUTF8",
+                ));
+            }
+            mail_options.push(MailParameter::SmtpUtfEight);
+        }
+
+        // Check for non-ascii content in the message
+        if !email.is_ascii() {
+            if !self.server_info().supports_feature(Extension::EightBitMime) {
+                return Err(error::client(
+                    "Message contains non-ascii chars but server does not support 8BITMIME",
+                ));
+            }
             mail_options.push(MailParameter::Body(MailBodyParameter::EightBitMime));
         }
+
         try_smtp!(
             self.command(Mail::new(envelope.from().cloned(), mail_options)),
             self
@@ -116,22 +143,22 @@ impl SmtpConnection {
         hello_name: &ClientId,
     ) -> Result<(), Error> {
         if self.server_info.supports_feature(Extension::StartTls) {
-            #[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
+            #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
             {
                 try_smtp!(self.command(Starttls), self);
-                try_smtp!(self.stream.get_mut().upgrade_tls(tls_parameters), self);
+                self.stream.get_mut().upgrade_tls(tls_parameters)?;
                 #[cfg(feature = "tracing")]
                 tracing::debug!("connection encrypted");
                 // Send EHLO again
                 try_smtp!(self.ehlo(hello_name), self);
                 Ok(())
             }
-            #[cfg(not(any(feature = "native-tls", feature = "rustls-tls")))]
+            #[cfg(not(any(feature = "native-tls", feature = "rustls", feature = "boring-tls")))]
             // This should never happen as `Tls` can only be created
             // when a TLS library is enabled
             unreachable!("TLS support required but not supported");
         } else {
-            Err(Error::Client("STARTTLS is not supported on this server"))
+            Err(error::client("STARTTLS is not supported on this server"))
         }
     }
 
@@ -152,6 +179,7 @@ impl SmtpConnection {
             self.panic = true;
             let _ = self.command(Quit);
         }
+        let _ = self.stream.get_mut().shutdown(std::net::Shutdown::Both);
     }
 
     /// Sets the underlying stream
@@ -175,7 +203,7 @@ impl SmtpConnection {
         self.command(Noop).is_ok()
     }
 
-    /// Sends an AUTH command with the given mechanism, and handles challenge if needed
+    /// Sends an AUTH command with the given mechanism, and handles the challenge if needed
     pub fn auth(
         &mut self,
         mechanisms: &[Mechanism],
@@ -184,9 +212,7 @@ impl SmtpConnection {
         let mechanism = self
             .server_info
             .get_auth_mechanism(mechanisms)
-            .ok_or(Error::Client(
-                "No compatible authentication mechanism was found",
-            ))?;
+            .ok_or_else(|| error::client("No compatible authentication mechanism was found"))?;
 
         // Limit challenges to avoid blocking
         let mut challenges = 10;
@@ -205,7 +231,7 @@ impl SmtpConnection {
         }
 
         if challenges == 0 {
-            Err(Error::ResponseParsing("Unexpected number of challenges"))
+            Err(error::response("Unexpected number of challenges"))
         } else {
             Ok(response)
         }
@@ -213,11 +239,12 @@ impl SmtpConnection {
 
     /// Sends the message content
     pub fn message(&mut self, message: &[u8]) -> Result<Response, Error> {
-        let mut out_buf: Vec<u8> = vec![];
         let mut codec = ClientCodec::new();
+        let mut out_buf = Vec::with_capacity(message.len());
         codec.encode(message, &mut out_buf);
         self.write(out_buf.as_slice())?;
         self.write(b"\r\n.\r\n")?;
+
         self.read_response()
     }
 
@@ -229,8 +256,11 @@ impl SmtpConnection {
 
     /// Writes a string to the server
     fn write(&mut self, string: &[u8]) -> Result<(), Error> {
-        self.stream.get_mut().write_all(string)?;
-        self.stream.get_mut().flush()?;
+        self.stream
+            .get_mut()
+            .write_all(string)
+            .map_err(error::network)?;
+        self.stream.get_mut().flush().map_err(error::network)?;
 
         #[cfg(feature = "tracing")]
         tracing::debug!("Wrote: {}", escape_crlf(&String::from_utf8_lossy(string)));
@@ -241,27 +271,58 @@ impl SmtpConnection {
     pub fn read_response(&mut self) -> Result<Response, Error> {
         let mut buffer = String::with_capacity(100);
 
-        while self.stream.read_line(&mut buffer)? > 0 {
+        while self.stream.read_line(&mut buffer).map_err(error::network)? > 0 {
             #[cfg(feature = "tracing")]
             tracing::debug!("<< {}", escape_crlf(&buffer));
             match parse_response(&buffer) {
                 Ok((_remaining, response)) => {
-                    if response.is_positive() {
-                        return Ok(response);
-                    }
-
-                    return Err(response.into());
+                    return if response.is_positive() {
+                        Ok(response)
+                    } else {
+                        Err(error::code(
+                            response.code(),
+                            Some(response.message().collect()),
+                        ))
+                    };
                 }
                 Err(nom::Err::Failure(e)) => {
-                    return Err(Error::Parsing(e.code));
+                    return Err(error::response(e.to_string()));
                 }
                 Err(nom::Err::Incomplete(_)) => { /* read more */ }
                 Err(nom::Err::Error(e)) => {
-                    return Err(Error::Parsing(e.code));
+                    return Err(error::response(e.to_string()));
                 }
             }
         }
 
-        Err(io::Error::new(io::ErrorKind::Other, "incomplete").into())
+        Err(error::response("incomplete response"))
+    }
+
+    /// The X509 certificate of the server (DER encoded)
+    #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+    pub fn peer_certificate(&self) -> Result<Vec<u8>, Error> {
+        self.stream.get_ref().peer_certificate()
+    }
+
+    /// Currently this is only avaialable when using Boring TLS and
+    /// returns the result of the verification of the TLS certificate
+    /// presented by the peer, if any. Only the last error encountered
+    /// during verification is presented.
+    /// It can be useful when you don't want to fail outright the TLS
+    /// negotiation, for example when a self-signed certificate is
+    /// encountered, but still want to record metrics or log the fact.
+    /// When using DANE verification, the PKI root of trust moves from
+    /// the CAs to DNS, so self-signed certificates are permitted as long
+    /// as the TLSA records match the leaf or issuer certificates.
+    /// It cannot be called on non Boring TLS streams.
+    #[cfg(feature = "boring-tls")]
+    pub fn tls_verify_result(&self) -> Result<(), Error> {
+        self.stream.get_ref().tls_verify_result()
+    }
+
+    /// All the X509 certificates of the chain (DER encoded)
+    #[cfg(any(feature = "rustls", feature = "boring-tls"))]
+    pub fn certificate_chain(&self) -> Result<Vec<Vec<u8>>, Error> {
+        self.stream.get_ref().certificate_chain()
     }
 }

src/transport/smtp/client/mock.rs

@@ -1,122 +0,0 @@
-#![allow(missing_docs)]
-// Comes from https://github.com/inre/rust-mq/blob/master/netopt
-
-use std::{
-    io::{self, Cursor, Read, Write},
-    sync::{Arc, Mutex},
-};
-
-pub type MockCursor = Cursor<Vec<u8>>;
-
-#[derive(Clone, Debug)]
-pub struct MockStream {
-    reader: Arc<Mutex<MockCursor>>,
-    writer: Arc<Mutex<MockCursor>>,
-}
-
-impl Default for MockStream {
-    fn default() -> Self {
-        Self::new()
-    }
-}
-
-impl MockStream {
-    pub fn new() -> MockStream {
-        MockStream {
-            reader: Arc::new(Mutex::new(MockCursor::new(Vec::new()))),
-            writer: Arc::new(Mutex::new(MockCursor::new(Vec::new()))),
-        }
-    }
-
-    pub fn with_vec(vec: Vec<u8>) -> MockStream {
-        MockStream {
-            reader: Arc::new(Mutex::new(MockCursor::new(vec))),
-            writer: Arc::new(Mutex::new(MockCursor::new(Vec::new()))),
-        }
-    }
-
-    pub fn take_vec(&mut self) -> Vec<u8> {
-        let mut cursor = self.writer.lock().unwrap();
-        let vec = cursor.get_ref().to_vec();
-        cursor.set_position(0);
-        cursor.get_mut().clear();
-        vec
-    }
-
-    pub fn next_vec(&mut self, vec: &[u8]) {
-        let mut cursor = self.reader.lock().unwrap();
-        cursor.set_position(0);
-        cursor.get_mut().clear();
-        cursor.get_mut().extend_from_slice(vec);
-    }
-
-    pub fn swap(&mut self) {
-        let mut cur_write = self.writer.lock().unwrap();
-        let mut cur_read = self.reader.lock().unwrap();
-        let vec_write = cur_write.get_ref().to_vec();
-        let vec_read = cur_read.get_ref().to_vec();
-        cur_write.set_position(0);
-        cur_read.set_position(0);
-        cur_write.get_mut().clear();
-        cur_read.get_mut().clear();
-        // swap cursors
-        cur_read.get_mut().extend_from_slice(vec_write.as_slice());
-        cur_write.get_mut().extend_from_slice(vec_read.as_slice());
-    }
-}
-
-impl Write for MockStream {
-    fn write(&mut self, msg: &[u8]) -> io::Result<usize> {
-        self.writer.lock().unwrap().write(msg)
-    }
-
-    fn flush(&mut self) -> io::Result<()> {
-        self.writer.lock().unwrap().flush()
-    }
-}
-
-impl Read for MockStream {
-    fn read(&mut self, buf: &mut [u8]) -> io::Result<usize> {
-        self.reader.lock().unwrap().read(buf)
-    }
-}
-
-#[cfg(test)]
-mod test {
-    use super::MockStream;
-    use std::io::{Read, Write};
-
-    #[test]
-    fn write_take_test() {
-        let mut mock = MockStream::new();
-        // write to mock stream
-        mock.write_all(&[1, 2, 3]).unwrap();
-        assert_eq!(mock.take_vec(), vec![1, 2, 3]);
-    }
-
-    #[test]
-    fn read_with_vec_test() {
-        let mut mock = MockStream::with_vec(vec![4, 5]);
-        let mut vec = Vec::new();
-        mock.read_to_end(&mut vec).unwrap();
-        assert_eq!(vec, vec![4, 5]);
-    }
-
-    #[test]
-    fn clone_test() {
-        let mut mock = MockStream::new();
-        let mut cloned = mock.clone();
-        mock.write_all(&[6, 7]).unwrap();
-        assert_eq!(cloned.take_vec(), vec![6, 7]);
-    }
-
-    #[test]
-    fn swap_test() {
-        let mut mock = MockStream::new();
-        let mut vec = Vec::new();
-        mock.write_all(&[8, 9, 10]).unwrap();
-        mock.swap();
-        mock.read_to_end(&mut vec).unwrap();
-        assert_eq!(vec, vec![8, 9, 10]);
-    }
-}

src/transport/smtp/client/mod.rs

@@ -7,16 +7,14 @@
 //!
 //! # #[cfg(feature = "smtp-transport")]
 //! # fn main() -> Result<(), Box<dyn Error>> {
-//! use lettre::transport::smtp::{SMTP_PORT, extension::ClientId, commands::*, client::SmtpConnection};
+//! use lettre::transport::smtp::{
+//!     client::SmtpConnection, commands::*, extension::ClientId, SMTP_PORT,
+//! };
 //!
-//! let hello = ClientId::Domain("my_hostname".to_string());
-//! let mut client = SmtpConnection::connect(&("localhost", SMTP_PORT), None, &hello, None)?;
-//! client.command(
-//!         Mail::new(Some("user@example.com".parse()?), vec![])
-//!     )?;
-//! client.command(
-//!         Rcpt::new("user@example.org".parse()?, vec![])
-//!       )?;
+//! let hello = ClientId::Domain("my_hostname".to_owned());
+//! let mut client = SmtpConnection::connect(&("localhost", SMTP_PORT), None, &hello, None, None)?;
+//! client.command(Mail::new(Some("user@example.com".parse()?), vec![]))?;
+//! client.command(Rcpt::new("user@example.org".parse()?, vec![]))?;
 //! client.command(Data)?;
 //! client.message("Test email".as_bytes())?;
 //! client.command(Quit)?;
@@ -27,75 +25,83 @@
 #[cfg(feature = "serde")]
 use std::fmt::Debug;
 
-#[cfg(any(feature = "tokio02", feature = "tokio1", feature = "async-std1"))]
-pub(crate) use self::async_connection::AsyncSmtpConnection;
-#[cfg(any(feature = "tokio02", feature = "tokio1", feature = "async-std1"))]
-pub(crate) use self::async_net::AsyncNetworkStream;
+#[cfg(any(feature = "tokio1", feature = "async-std1"))]
+pub use self::async_connection::AsyncSmtpConnection;
+#[cfg(any(feature = "tokio1", feature = "async-std1"))]
+#[allow(deprecated)]
+pub use self::async_net::AsyncNetworkStream;
+#[cfg(feature = "tokio1")]
+pub use self::async_net::AsyncTokioStream;
 use self::net::NetworkStream;
-#[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
+#[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
 pub(super) use self::tls::InnerTlsParameters;
+#[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+pub use self::tls::TlsVersion;
 pub use self::{
     connection::SmtpConnection,
-    mock::MockStream,
-    tls::{Certificate, Tls, TlsParameters, TlsParametersBuilder},
+    tls::{Certificate, CertificateStore, Identity, Tls, TlsParameters, TlsParametersBuilder},
 };
 
-#[cfg(any(feature = "tokio02", feature = "tokio1", feature = "async-std1"))]
+#[cfg(any(feature = "tokio1", feature = "async-std1"))]
 mod async_connection;
-#[cfg(any(feature = "tokio02", feature = "tokio1", feature = "async-std1"))]
+#[cfg(any(feature = "tokio1", feature = "async-std1"))]
 mod async_net;
 mod connection;
-mod mock;
 mod net;
 mod tls;
 
 /// The codec used for transparency
-#[derive(Default, Clone, Copy, Debug)]
-#[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
-pub struct ClientCodec {
-    escape_count: u8,
+#[derive(Debug)]
+struct ClientCodec {
+    status: CodecStatus,
 }
 
 impl ClientCodec {
     /// Creates a new client codec
-    pub fn new() -> Self {
-        ClientCodec::default()
+    pub(crate) fn new() -> Self {
+        Self {
+            status: CodecStatus::StartOfNewLine,
+        }
     }
 
     /// Adds transparency
     fn encode(&mut self, frame: &[u8], buf: &mut Vec<u8>) {
-        match frame.len() {
-            0 => {
-                match self.escape_count {
-                    0 => buf.extend_from_slice(b"\r\n.\r\n"),
-                    1 => buf.extend_from_slice(b"\n.\r\n"),
-                    2 => buf.extend_from_slice(b".\r\n"),
-                    _ => unreachable!(),
+        for &b in frame {
+            buf.push(b);
+            match (b, self.status) {
+                (b'\r', _) => {
+                    self.status = CodecStatus::StartingNewLine;
                 }
-                self.escape_count = 0;
-            }
-            _ => {
-                let mut start = 0;
-                for (idx, byte) in frame.iter().enumerate() {
-                    match self.escape_count {
-                        0 => self.escape_count = if *byte == b'\r' { 1 } else { 0 },
-                        1 => self.escape_count = if *byte == b'\n' { 2 } else { 0 },
-                        2 => self.escape_count = if *byte == b'.' { 3 } else { 0 },
-                        _ => unreachable!(),
-                    }
-                    if self.escape_count == 3 {
-                        self.escape_count = 0;
-                        buf.extend_from_slice(&frame[start..idx]);
-                        buf.extend_from_slice(b".");
-                        start = idx;
-                    }
+                (b'\n', CodecStatus::StartingNewLine) => {
+                    self.status = CodecStatus::StartOfNewLine;
                 }
-                buf.extend_from_slice(&frame[start..]);
+                (_, CodecStatus::StartingNewLine) => {
+                    self.status = CodecStatus::MiddleOfLine;
+                }
+                (b'.', CodecStatus::StartOfNewLine) => {
+                    self.status = CodecStatus::MiddleOfLine;
+                    buf.push(b'.');
+                }
+                (_, CodecStatus::StartOfNewLine) => {
+                    self.status = CodecStatus::MiddleOfLine;
+                }
+                _ => {}
             }
         }
     }
 }
 
+#[derive(Debug, Copy, Clone)]
+#[allow(clippy::enum_variant_names)]
+enum CodecStatus {
+    /// We are past the first character of the current line
+    MiddleOfLine,
+    /// We just read a `\r` character
+    StartingNewLine,
+    /// We are at the start of a new line
+    StartOfNewLine,
+}
+
 /// Returns the string replacing all the CRLF with "\<CRLF\>"
 /// Used for debug displays
 #[cfg(feature = "tracing")]
@@ -109,10 +115,12 @@ mod test {
 
     #[test]
     fn test_codec() {
+        let mut buf = Vec::new();
         let mut codec = ClientCodec::new();
-        let mut buf: Vec<u8> = vec![];
 
+        codec.encode(b".\r\n", &mut buf);
         codec.encode(b"test\r\n", &mut buf);
+        codec.encode(b"test\r\n\r\n", &mut buf);
         codec.encode(b".\r\n", &mut buf);
         codec.encode(b"\r\ntest", &mut buf);
         codec.encode(b"te\r\n.\r\nst", &mut buf);
@@ -121,14 +129,18 @@ mod test {
         codec.encode(b"test\n", &mut buf);
         codec.encode(b".test\n", &mut buf);
         codec.encode(b"test", &mut buf);
+        codec.encode(b"test", &mut buf);
+        codec.encode(b"test\r\n", &mut buf);
+        codec.encode(b".test\r\n", &mut buf);
+        codec.encode(b"test.\r\n", &mut buf);
         assert_eq!(
             String::from_utf8(buf).unwrap(),
-            "test\r\n..\r\n\r\ntestte\r\n..\r\nsttesttest.test\n.test\ntest"
+            "..\r\ntest\r\ntest\r\n\r\n..\r\n\r\ntestte\r\n..\r\nsttesttest.test\n.test\ntesttesttest\r\n..test\r\ntest.\r\n"
         );
     }
 
     #[test]
-    #[cfg(feature = "log")]
+    #[cfg(feature = "tracing")]
     fn test_escape_crlf() {
         assert_eq!(escape_crlf("\r\n"), "<CRLF>");
         assert_eq!(escape_crlf("EHLO my_name\r\n"), "EHLO my_name<CRLF>");

src/transport/smtp/client/net.rs

@@ -1,21 +1,24 @@
-#[cfg(feature = "rustls-tls")]
+#[cfg(feature = "rustls")]
 use std::sync::Arc;
 use std::{
     io::{self, Read, Write},
-    net::{Ipv4Addr, Shutdown, SocketAddr, SocketAddrV4, TcpStream, ToSocketAddrs},
+    mem,
+    net::{IpAddr, Ipv4Addr, Shutdown, SocketAddr, SocketAddrV4, TcpStream, ToSocketAddrs},
     time::Duration,
 };
 
+#[cfg(feature = "boring-tls")]
+use boring::ssl::SslStream;
 #[cfg(feature = "native-tls")]
 use native_tls::TlsStream;
+#[cfg(feature = "rustls")]
+use rustls::{pki_types::ServerName, ClientConnection, StreamOwned};
+use socket2::{Domain, Protocol, Type};
 
-#[cfg(feature = "rustls-tls")]
-use rustls::{ClientSession, StreamOwned};
-
-#[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
+#[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
 use super::InnerTlsParameters;
-use super::{MockStream, TlsParameters};
-use crate::transport::smtp::Error;
+use super::TlsParameters;
+use crate::transport::smtp::{error, Error};
 
 /// A network stream
 pub struct NetworkStream {
@@ -33,45 +36,57 @@ enum InnerNetworkStream {
     #[cfg(feature = "native-tls")]
     NativeTls(TlsStream<TcpStream>),
     /// Encrypted TCP stream
-    #[cfg(feature = "rustls-tls")]
-    RustlsTls(StreamOwned<ClientSession, TcpStream>),
-    /// Mock stream
-    Mock(MockStream),
+    #[cfg(feature = "rustls")]
+    RustlsTls(StreamOwned<ClientConnection, TcpStream>),
+    #[cfg(feature = "boring-tls")]
+    BoringTls(SslStream<TcpStream>),
+    /// Can't be built
+    None,
 }
 
 impl NetworkStream {
     fn new(inner: InnerNetworkStream) -> Self {
-        NetworkStream { inner }
-    }
+        if let InnerNetworkStream::None = inner {
+            debug_assert!(false, "InnerNetworkStream::None must never be built");
+        }
 
-    pub fn new_mock(mock: MockStream) -> Self {
-        Self::new(InnerNetworkStream::Mock(mock))
+        NetworkStream { inner }
     }
 
     /// Returns peer's address
     pub fn peer_addr(&self) -> io::Result<SocketAddr> {
-        match self.inner {
-            InnerNetworkStream::Tcp(ref s) => s.peer_addr(),
+        match &self.inner {
+            InnerNetworkStream::Tcp(s) => s.peer_addr(),
             #[cfg(feature = "native-tls")]
-            InnerNetworkStream::NativeTls(ref s) => s.get_ref().peer_addr(),
-            #[cfg(feature = "rustls-tls")]
-            InnerNetworkStream::RustlsTls(ref s) => s.get_ref().peer_addr(),
-            InnerNetworkStream::Mock(_) => Ok(SocketAddr::V4(SocketAddrV4::new(
-                Ipv4Addr::new(127, 0, 0, 1),
-                80,
-            ))),
+            InnerNetworkStream::NativeTls(s) => s.get_ref().peer_addr(),
+            #[cfg(feature = "rustls")]
+            InnerNetworkStream::RustlsTls(s) => s.get_ref().peer_addr(),
+            #[cfg(feature = "boring-tls")]
+            InnerNetworkStream::BoringTls(s) => s.get_ref().peer_addr(),
+            InnerNetworkStream::None => {
+                debug_assert!(false, "InnerNetworkStream::None must never be built");
+                Ok(SocketAddr::V4(SocketAddrV4::new(
+                    Ipv4Addr::new(127, 0, 0, 1),
+                    80,
+                )))
+            }
         }
     }
 
     /// Shutdowns the connection
     pub fn shutdown(&self, how: Shutdown) -> io::Result<()> {
-        match self.inner {
-            InnerNetworkStream::Tcp(ref s) => s.shutdown(how),
+        match &self.inner {
+            InnerNetworkStream::Tcp(s) => s.shutdown(how),
             #[cfg(feature = "native-tls")]
-            InnerNetworkStream::NativeTls(ref s) => s.get_ref().shutdown(how),
-            #[cfg(feature = "rustls-tls")]
-            InnerNetworkStream::RustlsTls(ref s) => s.get_ref().shutdown(how),
-            InnerNetworkStream::Mock(_) => Ok(()),
+            InnerNetworkStream::NativeTls(s) => s.get_ref().shutdown(how),
+            #[cfg(feature = "rustls")]
+            InnerNetworkStream::RustlsTls(s) => s.get_ref().shutdown(how),
+            #[cfg(feature = "boring-tls")]
+            InnerNetworkStream::BoringTls(s) => s.get_ref().shutdown(how),
+            InnerNetworkStream::None => {
+                debug_assert!(false, "InnerNetworkStream::None must never be built");
+                Ok(())
+            }
         }
     }
 
@@ -79,25 +94,49 @@ impl NetworkStream {
         server: T,
         timeout: Option<Duration>,
         tls_parameters: Option<&TlsParameters>,
+        local_addr: Option<IpAddr>,
     ) -> Result<NetworkStream, Error> {
-        fn try_connect_timeout<T: ToSocketAddrs>(
+        fn try_connect<T: ToSocketAddrs>(
             server: T,
-            timeout: Duration,
+            timeout: Option<Duration>,
+            local_addr: Option<IpAddr>,
         ) -> Result<TcpStream, Error> {
-            let addrs = server.to_socket_addrs()?;
+            let addrs = server
+                .to_socket_addrs()
+                .map_err(error::connection)?
+                .filter(|resolved_addr| resolved_address_filter(resolved_addr, local_addr));
+
+            let mut last_err = None;
+
             for addr in addrs {
-                if let Ok(result) = TcpStream::connect_timeout(&addr, timeout) {
-                    return Ok(result);
+                let socket = socket2::Socket::new(
+                    Domain::for_address(addr),
+                    Type::STREAM,
+                    Some(Protocol::TCP),
+                )
+                .map_err(error::connection)?;
+                bind_local_address(&socket, &addr, local_addr)?;
+
+                if let Some(timeout) = timeout {
+                    match socket.connect_timeout(&addr.into(), timeout) {
+                        Ok(()) => return Ok(socket.into()),
+                        Err(err) => last_err = Some(err),
+                    }
+                } else {
+                    match socket.connect(&addr.into()) {
+                        Ok(()) => return Ok(socket.into()),
+                        Err(err) => last_err = Some(err),
+                    }
                 }
             }
-            Err(Error::Client("Could not connect"))
+
+            Err(match last_err {
+                Some(last_err) => error::connection(last_err),
+                None => error::connection("could not resolve to any address"),
+            })
         }
 
-        let tcp_stream = match timeout {
-            Some(t) => try_connect_timeout(server, t)?,
-            None => TcpStream::connect(server)?,
-        };
-
+        let tcp_stream = try_connect(server, timeout, local_addr)?;
         let mut stream = NetworkStream::new(InnerNetworkStream::Tcp(tcp_stream));
         if let Some(tls_parameters) = tls_parameters {
             stream.upgrade_tls(tls_parameters)?;
@@ -107,20 +146,18 @@ impl NetworkStream {
 
     pub fn upgrade_tls(&mut self, tls_parameters: &TlsParameters) -> Result<(), Error> {
         match &self.inner {
-            #[cfg(not(any(feature = "native-tls", feature = "rustls-tls")))]
+            #[cfg(not(any(feature = "native-tls", feature = "rustls", feature = "boring-tls")))]
             InnerNetworkStream::Tcp(_) => {
                 let _ = tls_parameters;
-                panic!("Trying to upgrade an NetworkStream without having enabled either the native-tls or the rustls-tls feature");
+                panic!("Trying to upgrade an NetworkStream without having enabled either the `native-tls` or the `rustls` feature");
             }
 
-            #[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
+            #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
             InnerNetworkStream::Tcp(_) => {
                 // get owned TcpStream
-                let tcp_stream =
-                    std::mem::replace(&mut self.inner, InnerNetworkStream::Mock(MockStream::new()));
-                let tcp_stream = match tcp_stream {
-                    InnerNetworkStream::Tcp(tcp_stream) => tcp_stream,
-                    _ => unreachable!(),
+                let tcp_stream = mem::replace(&mut self.inner, InnerNetworkStream::None);
+                let InnerNetworkStream::Tcp(tcp_stream) = tcp_stream else {
+                    unreachable!()
                 };
 
                 self.inner = Self::upgrade_tls_impl(tcp_stream, tls_parameters)?;
@@ -130,7 +167,7 @@ impl NetworkStream {
         }
     }
 
-    #[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
+    #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
     fn upgrade_tls_impl(
         tcp_stream: TcpStream,
         tls_parameters: &TlsParameters,
@@ -140,101 +177,246 @@ impl NetworkStream {
             InnerTlsParameters::NativeTls(connector) => {
                 let stream = connector
                     .connect(tls_parameters.domain(), tcp_stream)
-                    .map_err(|err| Error::Io(io::Error::new(io::ErrorKind::Other, err)))?;
+                    .map_err(error::connection)?;
                 InnerNetworkStream::NativeTls(stream)
             }
-            #[cfg(feature = "rustls-tls")]
+            #[cfg(feature = "rustls")]
             InnerTlsParameters::RustlsTls(connector) => {
-                use webpki::DNSNameRef;
-
-                let domain = DNSNameRef::try_from_ascii_str(tls_parameters.domain())?;
-                let stream = StreamOwned::new(
-                    ClientSession::new(&Arc::new(connector.clone()), domain),
-                    tcp_stream,
-                );
-
+                let domain = ServerName::try_from(tls_parameters.domain())
+                    .map_err(|_| error::connection("domain isn't a valid DNS name"))?;
+                let connection = ClientConnection::new(Arc::clone(connector), domain.to_owned())
+                    .map_err(error::connection)?;
+                let stream = StreamOwned::new(connection, tcp_stream);
                 InnerNetworkStream::RustlsTls(stream)
             }
+            #[cfg(feature = "boring-tls")]
+            InnerTlsParameters::BoringTls(connector) => {
+                let stream = connector
+                    .configure()
+                    .map_err(error::connection)?
+                    .verify_hostname(tls_parameters.accept_invalid_hostnames)
+                    .connect(tls_parameters.domain(), tcp_stream)
+                    .map_err(error::connection)?;
+                InnerNetworkStream::BoringTls(stream)
+            }
         })
     }
 
     pub fn is_encrypted(&self) -> bool {
-        match self.inner {
-            InnerNetworkStream::Tcp(_) | InnerNetworkStream::Mock(_) => false,
+        match &self.inner {
+            InnerNetworkStream::Tcp(_) => false,
             #[cfg(feature = "native-tls")]
             InnerNetworkStream::NativeTls(_) => true,
-            #[cfg(feature = "rustls-tls")]
+            #[cfg(feature = "rustls")]
             InnerNetworkStream::RustlsTls(_) => true,
+            #[cfg(feature = "boring-tls")]
+            InnerNetworkStream::BoringTls(_) => true,
+            InnerNetworkStream::None => {
+                debug_assert!(false, "InnerNetworkStream::None must never be built");
+                false
+            }
+        }
+    }
+
+    #[cfg(feature = "boring-tls")]
+    pub fn tls_verify_result(&self) -> Result<(), Error> {
+        match &self.inner {
+            InnerNetworkStream::Tcp(_) => Err(error::client("Connection is not encrypted")),
+            #[cfg(feature = "native-tls")]
+            InnerNetworkStream::NativeTls(_) => panic!("Unsupported"),
+            #[cfg(feature = "rustls")]
+            InnerNetworkStream::RustlsTls(_) => panic!("Unsupported"),
+            #[cfg(feature = "boring-tls")]
+            InnerNetworkStream::BoringTls(stream) => {
+                stream.ssl().verify_result().map_err(error::tls)
+            }
+            InnerNetworkStream::None => panic!("InnerNetworkStream::None must never be built"),
+        }
+    }
+
+    #[cfg(any(feature = "rustls", feature = "boring-tls"))]
+    pub fn certificate_chain(&self) -> Result<Vec<Vec<u8>>, Error> {
+        match &self.inner {
+            InnerNetworkStream::Tcp(_) => Err(error::client("Connection is not encrypted")),
+            #[cfg(feature = "native-tls")]
+            InnerNetworkStream::NativeTls(_) => panic!("Unsupported"),
+            #[cfg(feature = "rustls")]
+            InnerNetworkStream::RustlsTls(stream) => Ok(stream
+                .conn
+                .peer_certificates()
+                .unwrap()
+                .iter()
+                .map(|c| c.to_vec())
+                .collect()),
+            #[cfg(feature = "boring-tls")]
+            InnerNetworkStream::BoringTls(stream) => Ok(stream
+                .ssl()
+                .peer_cert_chain()
+                .unwrap()
+                .iter()
+                .map(|c| c.to_der().map_err(error::tls))
+                .collect::<Result<Vec<_>, _>>()?),
+            InnerNetworkStream::None => panic!("InnerNetworkStream::None must never be built"),
+        }
+    }
+
+    #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+    pub fn peer_certificate(&self) -> Result<Vec<u8>, Error> {
+        match &self.inner {
+            InnerNetworkStream::Tcp(_) => Err(error::client("Connection is not encrypted")),
+            #[cfg(feature = "native-tls")]
+            InnerNetworkStream::NativeTls(stream) => Ok(stream
+                .peer_certificate()
+                .map_err(error::tls)?
+                .unwrap()
+                .to_der()
+                .map_err(error::tls)?),
+            #[cfg(feature = "rustls")]
+            InnerNetworkStream::RustlsTls(stream) => Ok(stream
+                .conn
+                .peer_certificates()
+                .unwrap()
+                .first()
+                .unwrap()
+                .to_vec()),
+            #[cfg(feature = "boring-tls")]
+            InnerNetworkStream::BoringTls(stream) => Ok(stream
+                .ssl()
+                .peer_certificate()
+                .unwrap()
+                .to_der()
+                .map_err(error::tls)?),
+            InnerNetworkStream::None => panic!("InnerNetworkStream::None must never be built"),
         }
     }
 
     pub fn set_read_timeout(&mut self, duration: Option<Duration>) -> io::Result<()> {
-        match self.inner {
-            InnerNetworkStream::Tcp(ref mut stream) => stream.set_read_timeout(duration),
+        match &mut self.inner {
+            InnerNetworkStream::Tcp(stream) => stream.set_read_timeout(duration),
             #[cfg(feature = "native-tls")]
-            InnerNetworkStream::NativeTls(ref mut stream) => {
-                stream.get_ref().set_read_timeout(duration)
+            InnerNetworkStream::NativeTls(stream) => stream.get_ref().set_read_timeout(duration),
+            #[cfg(feature = "rustls")]
+            InnerNetworkStream::RustlsTls(stream) => stream.get_ref().set_read_timeout(duration),
+            #[cfg(feature = "boring-tls")]
+            InnerNetworkStream::BoringTls(stream) => stream.get_ref().set_read_timeout(duration),
+            InnerNetworkStream::None => {
+                debug_assert!(false, "InnerNetworkStream::None must never be built");
+                Ok(())
             }
-            #[cfg(feature = "rustls-tls")]
-            InnerNetworkStream::RustlsTls(ref mut stream) => {
-                stream.get_ref().set_read_timeout(duration)
-            }
-            InnerNetworkStream::Mock(_) => Ok(()),
         }
     }
 
     /// Set write timeout for IO calls
     pub fn set_write_timeout(&mut self, duration: Option<Duration>) -> io::Result<()> {
-        match self.inner {
-            InnerNetworkStream::Tcp(ref mut stream) => stream.set_write_timeout(duration),
+        match &mut self.inner {
+            InnerNetworkStream::Tcp(stream) => stream.set_write_timeout(duration),
 
             #[cfg(feature = "native-tls")]
-            InnerNetworkStream::NativeTls(ref mut stream) => {
-                stream.get_ref().set_write_timeout(duration)
+            InnerNetworkStream::NativeTls(stream) => stream.get_ref().set_write_timeout(duration),
+            #[cfg(feature = "rustls")]
+            InnerNetworkStream::RustlsTls(stream) => stream.get_ref().set_write_timeout(duration),
+            #[cfg(feature = "boring-tls")]
+            InnerNetworkStream::BoringTls(stream) => stream.get_ref().set_write_timeout(duration),
+            InnerNetworkStream::None => {
+                debug_assert!(false, "InnerNetworkStream::None must never be built");
+                Ok(())
             }
-            #[cfg(feature = "rustls-tls")]
-            InnerNetworkStream::RustlsTls(ref mut stream) => {
-                stream.get_ref().set_write_timeout(duration)
-            }
-
-            InnerNetworkStream::Mock(_) => Ok(()),
         }
     }
 }
 
 impl Read for NetworkStream {
     fn read(&mut self, buf: &mut [u8]) -> io::Result<usize> {
-        match self.inner {
-            InnerNetworkStream::Tcp(ref mut s) => s.read(buf),
+        match &mut self.inner {
+            InnerNetworkStream::Tcp(s) => s.read(buf),
             #[cfg(feature = "native-tls")]
-            InnerNetworkStream::NativeTls(ref mut s) => s.read(buf),
-            #[cfg(feature = "rustls-tls")]
-            InnerNetworkStream::RustlsTls(ref mut s) => s.read(buf),
-            InnerNetworkStream::Mock(ref mut s) => s.read(buf),
+            InnerNetworkStream::NativeTls(s) => s.read(buf),
+            #[cfg(feature = "rustls")]
+            InnerNetworkStream::RustlsTls(s) => s.read(buf),
+            #[cfg(feature = "boring-tls")]
+            InnerNetworkStream::BoringTls(s) => s.read(buf),
+            InnerNetworkStream::None => {
+                debug_assert!(false, "InnerNetworkStream::None must never be built");
+                Ok(0)
+            }
         }
     }
 }
 
 impl Write for NetworkStream {
     fn write(&mut self, buf: &[u8]) -> io::Result<usize> {
-        match self.inner {
-            InnerNetworkStream::Tcp(ref mut s) => s.write(buf),
+        match &mut self.inner {
+            InnerNetworkStream::Tcp(s) => s.write(buf),
             #[cfg(feature = "native-tls")]
-            InnerNetworkStream::NativeTls(ref mut s) => s.write(buf),
-            #[cfg(feature = "rustls-tls")]
-            InnerNetworkStream::RustlsTls(ref mut s) => s.write(buf),
-            InnerNetworkStream::Mock(ref mut s) => s.write(buf),
+            InnerNetworkStream::NativeTls(s) => s.write(buf),
+            #[cfg(feature = "rustls")]
+            InnerNetworkStream::RustlsTls(s) => s.write(buf),
+            #[cfg(feature = "boring-tls")]
+            InnerNetworkStream::BoringTls(s) => s.write(buf),
+            InnerNetworkStream::None => {
+                debug_assert!(false, "InnerNetworkStream::None must never be built");
+                Ok(0)
+            }
         }
     }
 
     fn flush(&mut self) -> io::Result<()> {
-        match self.inner {
-            InnerNetworkStream::Tcp(ref mut s) => s.flush(),
+        match &mut self.inner {
+            InnerNetworkStream::Tcp(s) => s.flush(),
             #[cfg(feature = "native-tls")]
-            InnerNetworkStream::NativeTls(ref mut s) => s.flush(),
-            #[cfg(feature = "rustls-tls")]
-            InnerNetworkStream::RustlsTls(ref mut s) => s.flush(),
-            InnerNetworkStream::Mock(ref mut s) => s.flush(),
+            InnerNetworkStream::NativeTls(s) => s.flush(),
+            #[cfg(feature = "rustls")]
+            InnerNetworkStream::RustlsTls(s) => s.flush(),
+            #[cfg(feature = "boring-tls")]
+            InnerNetworkStream::BoringTls(s) => s.flush(),
+            InnerNetworkStream::None => {
+                debug_assert!(false, "InnerNetworkStream::None must never be built");
+                Ok(())
+            }
         }
     }
 }
+
+/// If the local address is set, binds the socket to this address.
+/// If local address is not set, then destination address is required to determine the default
+/// local address on some platforms.
+/// See: <https://github.com/hyperium/hyper/blob/faf24c6ad8eee1c3d5ccc9a4d4835717b8e2903f/src/client/connect/http.rs#L560>
+fn bind_local_address(
+    socket: &socket2::Socket,
+    dst_addr: &SocketAddr,
+    local_addr: Option<IpAddr>,
+) -> Result<(), Error> {
+    match local_addr {
+        Some(local_addr) => {
+            socket
+                .bind(&SocketAddr::new(local_addr, 0).into())
+                .map_err(error::connection)?;
+        }
+        _ => {
+            if cfg!(windows) {
+                // Windows requires a socket be bound before calling connect
+                let any: SocketAddr = match dst_addr {
+                    SocketAddr::V4(_) => ([0, 0, 0, 0], 0).into(),
+                    SocketAddr::V6(_) => ([0, 0, 0, 0, 0, 0, 0, 0], 0).into(),
+                };
+                socket.bind(&any.into()).map_err(error::connection)?;
+            }
+        }
+    }
+    Ok(())
+}
+
+/// When we have an iterator of resolved remote addresses, we must filter them to be the same
+/// protocol as the local address binding. If no local address is set, then all will be matched.
+pub(crate) fn resolved_address_filter(
+    resolved_addr: &SocketAddr,
+    local_addr: Option<IpAddr>,
+) -> bool {
+    match local_addr {
+        Some(local_addr) => match resolved_addr.ip() {
+            IpAddr::V4(_) => local_addr.is_ipv4(),
+            IpAddr::V6(_) => local_addr.is_ipv6(),
+        },
+        None => true,
+    }
+}

src/transport/smtp/client/tls.rs

@@ -1,54 +1,185 @@
-#[cfg(feature = "rustls-tls")]
+use std::fmt::{self, Debug};
+#[cfg(feature = "rustls")]
 use std::sync::Arc;
 
+#[cfg(feature = "boring-tls")]
+use boring::{
+    pkey::PKey,
+    ssl::{SslConnector, SslVersion},
+    x509::store::X509StoreBuilder,
+};
 #[cfg(feature = "native-tls")]
 use native_tls::{Protocol, TlsConnector};
-#[cfg(feature = "rustls-tls")]
-use rustls::{ClientConfig, RootCertStore, ServerCertVerified, ServerCertVerifier, TLSError};
-#[cfg(feature = "rustls-tls")]
-use webpki::DNSNameRef;
+#[cfg(feature = "rustls")]
+use rustls::{
+    client::danger::{HandshakeSignatureValid, ServerCertVerified, ServerCertVerifier},
+    crypto::{verify_tls12_signature, verify_tls13_signature, CryptoProvider},
+    pki_types::{self, pem::PemObject, CertificateDer, PrivateKeyDer, ServerName, UnixTime},
+    server::ParsedCertificate,
+    ClientConfig, DigitallySignedStruct, Error as TlsError, RootCertStore, SignatureScheme,
+};
 
-use crate::transport::smtp::error::Error;
+#[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+use crate::transport::smtp::{error, Error};
 
-/// Accepted protocols by default.
-/// This removes TLS 1.0 and 1.1 compared to tls-native defaults.
-// This is also rustls' default behavior
-#[cfg(feature = "native-tls")]
-const DEFAULT_TLS_MIN_PROTOCOL: Protocol = Protocol::Tlsv12;
+/// TLS protocol versions.
+#[derive(Debug, Copy, Clone)]
+#[non_exhaustive]
+#[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+pub enum TlsVersion {
+    /// TLS 1.0
+    ///
+    /// Should only be used when trying to support legacy
+    /// SMTP servers that haven't updated to
+    /// at least TLS 1.2 yet.
+    ///
+    /// Supported by `native-tls` and `boring-tls`.
+    Tlsv10,
+    /// TLS 1.1
+    ///
+    /// Should only be used when trying to support legacy
+    /// SMTP servers that haven't updated to
+    /// at least TLS 1.2 yet.
+    ///
+    /// Supported by `native-tls` and `boring-tls`.
+    Tlsv11,
+    /// TLS 1.2
+    ///
+    /// A good option for most SMTP servers.
+    ///
+    /// Supported by all TLS backends.
+    Tlsv12,
+    /// TLS 1.3
+    ///
+    /// The most secure option, although not supported by all SMTP servers.
+    ///
+    /// Although it is technically supported by all TLS backends,
+    /// trying to set it for `native-tls` will give a runtime error.
+    Tlsv13,
+}
 
-/// How to apply TLS to a client connection
+/// Specifies how to establish a TLS connection
+///
+/// TLDR: Use [`Tls::Wrapper`] or [`Tls::Required`] when
+/// connecting to a remote server, [`Tls::None`] when
+/// connecting to a local server.
 #[derive(Clone)]
 #[allow(missing_copy_implementations)]
 pub enum Tls {
-    /// Insecure connection only (for testing purposes)
+    /// Insecure (plaintext) connection only.
+    ///
+    /// This option **always** uses a plaintext connection and should only
+    /// be used for trusted local relays. It is **highly discouraged**
+    /// for remote servers, as it exposes credentials and emails to potential
+    /// interception.
+    ///
+    /// Note: Servers requiring credentials or emails to be sent over TLS
+    /// may reject connections when this option is used.
     None,
-    /// Start with insecure connection and use `STARTTLS` when available
-    #[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
+    /// Begin with a plaintext connection and attempt to use `STARTTLS` if available.
+    ///
+    /// lettre will try to upgrade to a TLS-secured connection but will fall back
+    /// to plaintext if the server does not support TLS. This option is provided for
+    /// compatibility but is **strongly discouraged**, as it exposes connections to
+    /// potential MITM (man-in-the-middle) attacks.
+    ///
+    /// Warning: A malicious intermediary could intercept the `STARTTLS` flag,
+    /// causing lettre to believe the server only supports plaintext connections.
+    #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+    #[cfg_attr(
+        docsrs,
+        doc(cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls")))
+    )]
     Opportunistic(TlsParameters),
-    /// Start with insecure connection and require `STARTTLS`
-    #[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
+    /// Begin with a plaintext connection and require `STARTTLS` for security.
+    ///
+    /// lettre will upgrade plaintext TCP connections to TLS before transmitting
+    /// any sensitive data. If the server does not support TLS, the connection
+    /// attempt will fail, ensuring no credentials or emails are sent in plaintext.
+    ///
+    /// Unlike [`Tls::Opportunistic`], this option is secure against MITM attacks.
+    /// For optimal security and performance, consider using [`Tls::Wrapper`] instead,
+    /// as it requires fewer roundtrips to establish a secure connection.
+    #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+    #[cfg_attr(
+        docsrs,
+        doc(cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls")))
+    )]
     Required(TlsParameters),
-    /// Use TLS wrapped connection
-    #[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
+    /// Establish a connection wrapped in TLS from the start.
+    ///
+    /// lettre connects to the server and immediately performs a TLS handshake.
+    /// If the handshake fails, the connection attempt is aborted without
+    /// transmitting any sensitive data.
+    ///
+    /// This is the fastest and most secure option for establishing a connection.
+    #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+    #[cfg_attr(
+        docsrs,
+        doc(cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls")))
+    )]
     Wrapper(TlsParameters),
 }
 
+impl Debug for Tls {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        match &self {
+            Self::None => f.pad("None"),
+            #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+            Self::Opportunistic(_) => f.pad("Opportunistic"),
+            #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+            Self::Required(_) => f.pad("Required"),
+            #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+            Self::Wrapper(_) => f.pad("Wrapper"),
+        }
+    }
+}
+
+/// Source for the base set of root certificates to trust.
+#[allow(missing_copy_implementations)]
+#[derive(Clone, Debug, Default)]
+pub enum CertificateStore {
+    /// Use the default for the TLS backend.
+    ///
+    /// For native-tls, this will use the system certificate store on Windows, the keychain on
+    /// macOS, and OpenSSL directories on Linux (usually `/etc/ssl`).
+    ///
+    /// For rustls, this will also use the system store if the `rustls-native-certs` feature is
+    /// enabled, or will fall back to `webpki-roots`.
+    ///
+    /// The boring-tls backend uses the same logic as OpenSSL on all platforms.
+    #[default]
+    Default,
+    /// Use a hardcoded set of Mozilla roots via the `webpki-roots` crate.
+    ///
+    /// This option is only available in the rustls backend.
+    #[cfg(all(feature = "rustls", feature = "webpki-roots"))]
+    WebpkiRoots,
+    /// Don't use any system certificates.
+    None,
+}
+
 /// Parameters to use for secure clients
 #[derive(Clone)]
-#[allow(missing_debug_implementations)]
 pub struct TlsParameters {
     pub(crate) connector: InnerTlsParameters,
     /// The domain name which is expected in the TLS certificate from the server
     pub(super) domain: String,
+    #[cfg(feature = "boring-tls")]
+    pub(super) accept_invalid_hostnames: bool,
 }
 
 /// Builder for `TlsParameters`
-#[derive(Clone)]
+#[derive(Debug, Clone)]
 pub struct TlsParametersBuilder {
     domain: String,
+    cert_store: CertificateStore,
     root_certs: Vec<Certificate>,
+    identity: Option<Identity>,
     accept_invalid_hostnames: bool,
     accept_invalid_certs: bool,
+    #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+    min_tls_version: TlsVersion,
 }
 
 impl TlsParametersBuilder {
@@ -56,20 +187,38 @@ impl TlsParametersBuilder {
     pub fn new(domain: String) -> Self {
         Self {
             domain,
+            cert_store: CertificateStore::Default,
             root_certs: Vec::new(),
+            identity: None,
             accept_invalid_hostnames: false,
             accept_invalid_certs: false,
+            #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+            min_tls_version: TlsVersion::Tlsv12,
         }
     }
 
+    /// Set the source for the base set of root certificates to trust.
+    pub fn certificate_store(mut self, cert_store: CertificateStore) -> Self {
+        self.cert_store = cert_store;
+        self
+    }
+
     /// Add a custom root certificate
     ///
-    /// Can be used to safely connect to a server using a self signed certificate, for example.
-    pub fn add_root_certificate(&mut self, cert: Certificate) -> &mut Self {
+    /// Can be used to safely connect to a server using a self-signed certificate, for example.
+    pub fn add_root_certificate(mut self, cert: Certificate) -> Self {
         self.root_certs.push(cert);
         self
     }
 
+    /// Add a client certificate
+    ///
+    /// Can be used to configure a client certificate to present to the server.
+    pub fn identify_with(mut self, identity: Identity) -> Self {
+        self.identity = Some(identity);
+        self
+    }
+
     /// Controls whether certificates with an invalid hostname are accepted
     ///
     /// Defaults to `false`.
@@ -81,18 +230,25 @@ impl TlsParametersBuilder {
     /// including those from other sites, are trusted.
     ///
     /// This method introduces significant vulnerabilities to man-in-the-middle attacks.
-    ///
-    /// Hostname verification can only be disabled with the `native-tls` TLS backend.
-    #[cfg(feature = "native-tls")]
-    #[cfg_attr(docsrs, doc(cfg(feature = "native-tls")))]
-    pub fn dangerous_accept_invalid_hostnames(
-        &mut self,
-        accept_invalid_hostnames: bool,
-    ) -> &mut Self {
+    #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+    #[cfg_attr(
+        docsrs,
+        doc(cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls")))
+    )]
+    pub fn dangerous_accept_invalid_hostnames(mut self, accept_invalid_hostnames: bool) -> Self {
         self.accept_invalid_hostnames = accept_invalid_hostnames;
         self
     }
 
+    /// Controls which minimum TLS version is allowed
+    ///
+    /// Defaults to [`Tlsv12`][TlsVersion::Tlsv12].
+    #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+    pub fn set_min_tls_version(mut self, min_tls_version: TlsVersion) -> Self {
+        self.min_tls_version = min_tls_version;
+        self
+    }
+
     /// Controls whether invalid certificates are accepted
     ///
     /// Defaults to `false`.
@@ -109,27 +265,25 @@ impl TlsParametersBuilder {
     ///
     /// This method should only be used as a last resort, as it introduces
     /// significant vulnerabilities to man-in-the-middle attacks.
-    pub fn dangerous_accept_invalid_certs(&mut self, accept_invalid_certs: bool) -> &mut Self {
+    pub fn dangerous_accept_invalid_certs(mut self, accept_invalid_certs: bool) -> Self {
         self.accept_invalid_certs = accept_invalid_certs;
         self
     }
 
-    /// Creates a new `TlsParameters` using native-tls or rustls
+    /// Creates a new `TlsParameters` using native-tls, boring-tls or rustls
     /// depending on which one is available
-    #[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
-    #[cfg_attr(docsrs, doc(cfg(any(feature = "native-tls", feature = "rustls-tls"))))]
-    // TODO: remove below line once native-tls is supported with async-std
-    #[allow(unreachable_code)]
+    #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+    #[cfg_attr(
+        docsrs,
+        doc(cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls")))
+    )]
     pub fn build(self) -> Result<TlsParameters, Error> {
-        // TODO: remove once native-tls is supported with async-std
-        #[cfg(all(feature = "rustls-tls", feature = "async-std1"))]
+        #[cfg(feature = "rustls")]
         return self.build_rustls();
-
-        #[cfg(feature = "native-tls")]
+        #[cfg(all(not(feature = "rustls"), feature = "native-tls"))]
         return self.build_native();
-
-        #[cfg(not(feature = "native-tls"))]
-        return self.build_rustls();
+        #[cfg(all(not(feature = "rustls"), feature = "boring-tls"))]
+        return self.build_boring();
     }
 
     /// Creates a new `TlsParameters` using native-tls with the provided configuration
@@ -138,65 +292,226 @@ impl TlsParametersBuilder {
     pub fn build_native(self) -> Result<TlsParameters, Error> {
         let mut tls_builder = TlsConnector::builder();
 
+        match self.cert_store {
+            CertificateStore::Default => {}
+            CertificateStore::None => {
+                tls_builder.disable_built_in_roots(true);
+            }
+            #[allow(unreachable_patterns)]
+            other => {
+                return Err(error::tls(format!(
+                    "{other:?} is not supported in native tls"
+                )))
+            }
+        }
         for cert in self.root_certs {
             tls_builder.add_root_certificate(cert.native_tls);
         }
         tls_builder.danger_accept_invalid_hostnames(self.accept_invalid_hostnames);
         tls_builder.danger_accept_invalid_certs(self.accept_invalid_certs);
 
-        tls_builder.min_protocol_version(Some(DEFAULT_TLS_MIN_PROTOCOL));
-        let connector = tls_builder.build()?;
+        let min_tls_version = match self.min_tls_version {
+            TlsVersion::Tlsv10 => Protocol::Tlsv10,
+            TlsVersion::Tlsv11 => Protocol::Tlsv11,
+            TlsVersion::Tlsv12 => Protocol::Tlsv12,
+            TlsVersion::Tlsv13 => {
+                return Err(error::tls(
+                    "min tls version Tlsv13 not supported in native tls",
+                ))
+            }
+        };
+
+        tls_builder.min_protocol_version(Some(min_tls_version));
+        if let Some(identity) = self.identity {
+            tls_builder.identity(identity.native_tls);
+        }
+
+        let connector = tls_builder.build().map_err(error::tls)?;
         Ok(TlsParameters {
             connector: InnerTlsParameters::NativeTls(connector),
             domain: self.domain,
+            #[cfg(feature = "boring-tls")]
+            accept_invalid_hostnames: self.accept_invalid_hostnames,
+        })
+    }
+
+    /// Creates a new `TlsParameters` using boring-tls with the provided configuration
+    #[cfg(feature = "boring-tls")]
+    #[cfg_attr(docsrs, doc(cfg(feature = "boring-tls")))]
+    pub fn build_boring(self) -> Result<TlsParameters, Error> {
+        use boring::ssl::{SslMethod, SslVerifyMode};
+
+        let mut tls_builder = SslConnector::builder(SslMethod::tls_client()).map_err(error::tls)?;
+
+        if self.accept_invalid_certs {
+            tls_builder.set_verify(SslVerifyMode::NONE);
+        } else {
+            match self.cert_store {
+                CertificateStore::Default => {}
+                CertificateStore::None => {
+                    // Replace the default store with an empty store.
+                    tls_builder
+                        .set_cert_store(X509StoreBuilder::new().map_err(error::tls)?.build());
+                }
+                #[allow(unreachable_patterns)]
+                other => {
+                    return Err(error::tls(format!(
+                        "{other:?} is not supported in boring tls"
+                    )))
+                }
+            }
+
+            let cert_store = tls_builder.cert_store_mut();
+
+            for cert in self.root_certs {
+                cert_store.add_cert(cert.boring_tls).map_err(error::tls)?;
+            }
+        }
+
+        if let Some(identity) = self.identity {
+            tls_builder
+                .set_certificate(identity.boring_tls.0.as_ref())
+                .map_err(error::tls)?;
+            tls_builder
+                .set_private_key(identity.boring_tls.1.as_ref())
+                .map_err(error::tls)?;
+        }
+
+        let min_tls_version = match self.min_tls_version {
+            TlsVersion::Tlsv10 => SslVersion::TLS1,
+            TlsVersion::Tlsv11 => SslVersion::TLS1_1,
+            TlsVersion::Tlsv12 => SslVersion::TLS1_2,
+            TlsVersion::Tlsv13 => SslVersion::TLS1_3,
+        };
+
+        tls_builder
+            .set_min_proto_version(Some(min_tls_version))
+            .map_err(error::tls)?;
+        let connector = tls_builder.build();
+        Ok(TlsParameters {
+            connector: InnerTlsParameters::BoringTls(connector),
+            domain: self.domain,
+            accept_invalid_hostnames: self.accept_invalid_hostnames,
         })
     }
 
     /// Creates a new `TlsParameters` using rustls with the provided configuration
-    #[cfg(feature = "rustls-tls")]
-    #[cfg_attr(docsrs, doc(cfg(feature = "rustls-tls")))]
+    #[cfg(feature = "rustls")]
+    #[cfg_attr(docsrs, doc(cfg(feature = "rustls")))]
     pub fn build_rustls(self) -> Result<TlsParameters, Error> {
-        use webpki_roots::TLS_SERVER_ROOTS;
+        let just_version3 = &[&rustls::version::TLS13];
+        let supported_versions = match self.min_tls_version {
+            TlsVersion::Tlsv10 => {
+                return Err(error::tls("min tls version Tlsv10 not supported in rustls"))
+            }
+            TlsVersion::Tlsv11 => {
+                return Err(error::tls("min tls version Tlsv11 not supported in rustls"))
+            }
+            TlsVersion::Tlsv12 => rustls::ALL_VERSIONS,
+            TlsVersion::Tlsv13 => just_version3,
+        };
 
-        let mut tls = ClientConfig::new();
+        let crypto_provider = crate::rustls_crypto::crypto_provider();
+        let tls = ClientConfig::builder_with_provider(Arc::clone(&crypto_provider))
+            .with_protocol_versions(supported_versions)
+            .map_err(error::tls)?;
 
+        // Build TLS config
+        let mut root_cert_store = RootCertStore::empty();
+
+        #[cfg(feature = "rustls-native-certs")]
+        fn load_native_roots(store: &mut RootCertStore) {
+            let rustls_native_certs::CertificateResult { certs, errors, .. } =
+                rustls_native_certs::load_native_certs();
+            let errors_len = errors.len();
+
+            let (added, ignored) = store.add_parsable_certificates(certs);
+            #[cfg(feature = "tracing")]
+            tracing::debug!(
+                "loaded platform certs with {errors_len} failing to load, {added} valid and {ignored} ignored (invalid) certs"
+            );
+            #[cfg(not(feature = "tracing"))]
+            let _ = (errors_len, added, ignored);
+        }
+
+        #[cfg(all(feature = "rustls", feature = "webpki-roots"))]
+        fn load_webpki_roots(store: &mut RootCertStore) {
+            store.extend(webpki_roots::TLS_SERVER_ROOTS.iter().cloned());
+        }
+
+        match self.cert_store {
+            CertificateStore::Default => {
+                #[cfg(feature = "rustls-native-certs")]
+                load_native_roots(&mut root_cert_store);
+                #[cfg(all(not(feature = "rustls-native-certs"), feature = "webpki-roots"))]
+                load_webpki_roots(&mut root_cert_store);
+            }
+            #[cfg(all(feature = "rustls", feature = "webpki-roots"))]
+            CertificateStore::WebpkiRoots => {
+                load_webpki_roots(&mut root_cert_store);
+            }
+            CertificateStore::None => {}
+        }
         for cert in self.root_certs {
             for rustls_cert in cert.rustls {
-                tls.root_store
-                    .add(&rustls_cert)
-                    .map_err(|_| Error::InvalidCertificate)?;
+                root_cert_store.add(rustls_cert).map_err(error::tls)?;
             }
         }
-        if self.accept_invalid_certs {
-            tls.dangerous()
-                .set_certificate_verifier(Arc::new(InvalidCertsVerifier {}));
-        }
 
-        tls.root_store.add_server_trust_anchors(&TLS_SERVER_ROOTS);
+        let tls = if self.accept_invalid_certs || self.accept_invalid_hostnames {
+            let verifier = InvalidCertsVerifier {
+                ignore_invalid_hostnames: self.accept_invalid_hostnames,
+                ignore_invalid_certs: self.accept_invalid_certs,
+                roots: root_cert_store,
+                crypto_provider,
+            };
+            tls.dangerous()
+                .with_custom_certificate_verifier(Arc::new(verifier))
+        } else {
+            tls.with_root_certificates(root_cert_store)
+        };
+
+        let tls = if let Some(identity) = self.identity {
+            let (client_certificates, private_key) = identity.rustls_tls;
+            tls.with_client_auth_cert(client_certificates, private_key)
+                .map_err(error::tls)?
+        } else {
+            tls.with_no_client_auth()
+        };
+
         Ok(TlsParameters {
-            connector: InnerTlsParameters::RustlsTls(tls),
+            connector: InnerTlsParameters::RustlsTls(Arc::new(tls)),
             domain: self.domain,
+            #[cfg(feature = "boring-tls")]
+            accept_invalid_hostnames: self.accept_invalid_hostnames,
         })
     }
 }
 
 #[derive(Clone)]
-pub enum InnerTlsParameters {
+#[allow(clippy::enum_variant_names)]
+pub(crate) enum InnerTlsParameters {
     #[cfg(feature = "native-tls")]
     NativeTls(TlsConnector),
-    #[cfg(feature = "rustls-tls")]
-    RustlsTls(ClientConfig),
+    #[cfg(feature = "rustls")]
+    RustlsTls(Arc<ClientConfig>),
+    #[cfg(feature = "boring-tls")]
+    BoringTls(SslConnector),
 }
 
 impl TlsParameters {
     /// Creates a new `TlsParameters` using native-tls or rustls
     /// depending on which one is available
-    #[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
-    #[cfg_attr(docsrs, doc(cfg(any(feature = "native-tls", feature = "rustls-tls"))))]
+    #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+    #[cfg_attr(
+        docsrs,
+        doc(cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls")))
+    )]
     pub fn new(domain: String) -> Result<Self, Error> {
         TlsParametersBuilder::new(domain).build()
     }
 
+    /// Creates a new `TlsParameters` builder
     pub fn builder(domain: String) -> TlsParametersBuilder {
         TlsParametersBuilder::new(domain)
     }
@@ -209,78 +524,231 @@ impl TlsParameters {
     }
 
     /// Creates a new `TlsParameters` using rustls
-    #[cfg(feature = "rustls-tls")]
-    #[cfg_attr(docsrs, doc(cfg(feature = "rustls-tls")))]
+    #[cfg(feature = "rustls")]
+    #[cfg_attr(docsrs, doc(cfg(feature = "rustls")))]
     pub fn new_rustls(domain: String) -> Result<Self, Error> {
         TlsParametersBuilder::new(domain).build_rustls()
     }
 
+    /// Creates a new `TlsParameters` using boring
+    #[cfg(feature = "boring-tls")]
+    #[cfg_attr(docsrs, doc(cfg(feature = "boring-tls")))]
+    pub fn new_boring(domain: String) -> Result<Self, Error> {
+        TlsParametersBuilder::new(domain).build_boring()
+    }
+
     pub fn domain(&self) -> &str {
         &self.domain
     }
 }
 
-/// A client certificate that can be used with [`TlsParametersBuilder::add_root_certificate`]
+/// A certificate that can be used with [`TlsParametersBuilder::add_root_certificate`]
 #[derive(Clone)]
 #[allow(missing_copy_implementations)]
 pub struct Certificate {
     #[cfg(feature = "native-tls")]
     native_tls: native_tls::Certificate,
-    #[cfg(feature = "rustls-tls")]
-    rustls: Vec<rustls::Certificate>,
+    #[cfg(feature = "rustls")]
+    rustls: Vec<CertificateDer<'static>>,
+    #[cfg(feature = "boring-tls")]
+    boring_tls: boring::x509::X509,
 }
 
+#[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
 impl Certificate {
     /// Create a `Certificate` from a DER encoded certificate
     pub fn from_der(der: Vec<u8>) -> Result<Self, Error> {
         #[cfg(feature = "native-tls")]
-        let native_tls_cert =
-            native_tls::Certificate::from_der(&der).map_err(|_| Error::InvalidCertificate)?;
+        let native_tls_cert = native_tls::Certificate::from_der(&der).map_err(error::tls)?;
+
+        #[cfg(feature = "boring-tls")]
+        let boring_tls_cert = boring::x509::X509::from_der(&der).map_err(error::tls)?;
 
         Ok(Self {
             #[cfg(feature = "native-tls")]
             native_tls: native_tls_cert,
-            #[cfg(feature = "rustls-tls")]
-            rustls: vec![rustls::Certificate(der)],
+            #[cfg(feature = "rustls")]
+            rustls: vec![der.into()],
+            #[cfg(feature = "boring-tls")]
+            boring_tls: boring_tls_cert,
         })
     }
 
     /// Create a `Certificate` from a PEM encoded certificate
     pub fn from_pem(pem: &[u8]) -> Result<Self, Error> {
         #[cfg(feature = "native-tls")]
-        let native_tls_cert =
-            native_tls::Certificate::from_pem(pem).map_err(|_| Error::InvalidCertificate)?;
+        let native_tls_cert = native_tls::Certificate::from_pem(pem).map_err(error::tls)?;
 
-        #[cfg(feature = "rustls-tls")]
+        #[cfg(feature = "boring-tls")]
+        let boring_tls_cert = boring::x509::X509::from_pem(pem).map_err(error::tls)?;
+
+        #[cfg(feature = "rustls")]
         let rustls_cert = {
-            use rustls::internal::pemfile;
-            use std::io::Cursor;
-
-            let mut pem = Cursor::new(pem);
-            pemfile::certs(&mut pem).map_err(|_| Error::InvalidCertificate)?
+            CertificateDer::pem_slice_iter(pem)
+                .collect::<Result<Vec<_>, pki_types::pem::Error>>()
+                .map_err(|_| error::tls("invalid certificates"))?
         };
 
         Ok(Self {
             #[cfg(feature = "native-tls")]
             native_tls: native_tls_cert,
-            #[cfg(feature = "rustls-tls")]
+            #[cfg(feature = "rustls")]
             rustls: rustls_cert,
+            #[cfg(feature = "boring-tls")]
+            boring_tls: boring_tls_cert,
         })
     }
 }
 
-#[cfg(feature = "rustls-tls")]
-struct InvalidCertsVerifier;
+impl Debug for Certificate {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        f.debug_struct("Certificate").finish()
+    }
+}
 
-#[cfg(feature = "rustls-tls")]
+/// An identity that can be used with [`TlsParametersBuilder::identify_with`]
+#[allow(missing_copy_implementations)]
+pub struct Identity {
+    #[cfg(feature = "native-tls")]
+    native_tls: native_tls::Identity,
+    #[cfg(feature = "rustls")]
+    rustls_tls: (Vec<CertificateDer<'static>>, PrivateKeyDer<'static>),
+    #[cfg(feature = "boring-tls")]
+    boring_tls: (boring::x509::X509, PKey<boring::pkey::Private>),
+}
+
+impl Debug for Identity {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        f.debug_struct("Identity").finish()
+    }
+}
+
+impl Clone for Identity {
+    fn clone(&self) -> Self {
+        Identity {
+            #[cfg(feature = "native-tls")]
+            native_tls: self.native_tls.clone(),
+            #[cfg(feature = "rustls")]
+            rustls_tls: (self.rustls_tls.0.clone(), self.rustls_tls.1.clone_key()),
+            #[cfg(feature = "boring-tls")]
+            boring_tls: (self.boring_tls.0.clone(), self.boring_tls.1.clone()),
+        }
+    }
+}
+
+#[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+impl Identity {
+    pub fn from_pem(pem: &[u8], key: &[u8]) -> Result<Self, Error> {
+        Ok(Self {
+            #[cfg(feature = "native-tls")]
+            native_tls: Identity::from_pem_native_tls(pem, key)?,
+            #[cfg(feature = "rustls")]
+            rustls_tls: Identity::from_pem_rustls_tls(pem, key)?,
+            #[cfg(feature = "boring-tls")]
+            boring_tls: Identity::from_pem_boring_tls(pem, key)?,
+        })
+    }
+
+    #[cfg(feature = "native-tls")]
+    fn from_pem_native_tls(pem: &[u8], key: &[u8]) -> Result<native_tls::Identity, Error> {
+        native_tls::Identity::from_pkcs8(pem, key).map_err(error::tls)
+    }
+
+    #[cfg(feature = "rustls")]
+    fn from_pem_rustls_tls(
+        pem: &[u8],
+        key: &[u8],
+    ) -> Result<(Vec<CertificateDer<'static>>, PrivateKeyDer<'static>), Error> {
+        let key = match PrivateKeyDer::from_pem_slice(key) {
+            Ok(key) => key,
+            Err(pki_types::pem::Error::NoItemsFound) => {
+                return Err(error::tls("no private key found"))
+            }
+            Err(err) => return Err(error::tls(err)),
+        };
+
+        Ok((vec![pem.to_owned().into()], key))
+    }
+
+    #[cfg(feature = "boring-tls")]
+    fn from_pem_boring_tls(
+        pem: &[u8],
+        key: &[u8],
+    ) -> Result<(boring::x509::X509, PKey<boring::pkey::Private>), Error> {
+        let cert = boring::x509::X509::from_pem(pem).map_err(error::tls)?;
+        let key = boring::pkey::PKey::private_key_from_pem(key).map_err(error::tls)?;
+        Ok((cert, key))
+    }
+}
+
+#[cfg(feature = "rustls")]
+#[derive(Debug)]
+struct InvalidCertsVerifier {
+    ignore_invalid_hostnames: bool,
+    ignore_invalid_certs: bool,
+    roots: RootCertStore,
+    crypto_provider: Arc<CryptoProvider>,
+}
+
+#[cfg(feature = "rustls")]
 impl ServerCertVerifier for InvalidCertsVerifier {
     fn verify_server_cert(
         &self,
-        _roots: &RootCertStore,
-        _presented_certs: &[rustls::Certificate],
-        _dns_name: DNSNameRef<'_>,
+        end_entity: &CertificateDer<'_>,
+        intermediates: &[CertificateDer<'_>],
+        server_name: &ServerName<'_>,
         _ocsp_response: &[u8],
-    ) -> Result<ServerCertVerified, TLSError> {
+        now: UnixTime,
+    ) -> Result<ServerCertVerified, TlsError> {
+        let cert = ParsedCertificate::try_from(end_entity)?;
+
+        if !self.ignore_invalid_certs {
+            rustls::client::verify_server_cert_signed_by_trust_anchor(
+                &cert,
+                &self.roots,
+                intermediates,
+                now,
+                self.crypto_provider.signature_verification_algorithms.all,
+            )?;
+        }
+
+        if !self.ignore_invalid_hostnames {
+            rustls::client::verify_server_name(&cert, server_name)?;
+        }
         Ok(ServerCertVerified::assertion())
     }
+
+    fn verify_tls12_signature(
+        &self,
+        message: &[u8],
+        cert: &CertificateDer<'_>,
+        dss: &DigitallySignedStruct,
+    ) -> Result<HandshakeSignatureValid, TlsError> {
+        verify_tls12_signature(
+            message,
+            cert,
+            dss,
+            &self.crypto_provider.signature_verification_algorithms,
+        )
+    }
+
+    fn verify_tls13_signature(
+        &self,
+        message: &[u8],
+        cert: &CertificateDer<'_>,
+        dss: &DigitallySignedStruct,
+    ) -> Result<HandshakeSignatureValid, TlsError> {
+        verify_tls13_signature(
+            message,
+            cert,
+            dss,
+            &self.crypto_provider.signature_verification_algorithms,
+        )
+    }
+
+    fn supported_verify_schemes(&self) -> Vec<SignatureScheme> {
+        self.crypto_provider
+            .signature_verification_algorithms
+            .supported_schemes()
+    }
 }

src/transport/smtp/commands.rs

@@ -1,18 +1,19 @@
 //! SMTP commands
 
+use std::fmt::{self, Display, Formatter};
+
 use crate::{
+    address::Address,
     transport::smtp::{
         authentication::{Credentials, Mechanism},
-        error::Error,
+        error::{self, Error},
         extension::{ClientId, MailParameter, RcptParameter},
         response::Response,
     },
-    Address,
 };
-use std::fmt::{self, Display, Formatter};
 
 /// EHLO command
-#[derive(PartialEq, Clone, Debug)]
+#[derive(PartialEq, Eq, Clone, Debug)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 pub struct Ehlo {
     client_id: ClientId,
@@ -32,7 +33,7 @@ impl Ehlo {
 }
 
 /// STARTTLS command
-#[derive(PartialEq, Clone, Debug, Copy)]
+#[derive(PartialEq, Eq, Clone, Debug, Copy)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 pub struct Starttls;
 
@@ -43,7 +44,7 @@ impl Display for Starttls {
 }
 
 /// MAIL command
-#[derive(PartialEq, Clone, Debug)]
+#[derive(PartialEq, Eq, Clone, Debug)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 pub struct Mail {
     sender: Option<Address>,
@@ -55,10 +56,10 @@ impl Display for Mail {
         write!(
             f,
             "MAIL FROM:<{}>",
-            self.sender.as_ref().map(|s| s.as_ref()).unwrap_or("")
+            self.sender.as_ref().map_or("", |s| s.as_ref())
         )?;
         for parameter in &self.parameters {
-            write!(f, " {}", parameter)?;
+            write!(f, " {parameter}")?;
         }
         f.write_str("\r\n")
     }
@@ -72,7 +73,7 @@ impl Mail {
 }
 
 /// RCPT command
-#[derive(PartialEq, Clone, Debug)]
+#[derive(PartialEq, Eq, Clone, Debug)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 pub struct Rcpt {
     recipient: Address,
@@ -83,7 +84,7 @@ impl Display for Rcpt {
     fn fmt(&self, f: &mut Formatter<'_>) -> fmt::Result {
         write!(f, "RCPT TO:<{}>", self.recipient)?;
         for parameter in &self.parameters {
-            write!(f, " {}", parameter)?;
+            write!(f, " {parameter}")?;
         }
         f.write_str("\r\n")
     }
@@ -100,7 +101,7 @@ impl Rcpt {
 }
 
 /// DATA command
-#[derive(PartialEq, Clone, Debug, Copy)]
+#[derive(PartialEq, Eq, Clone, Debug, Copy)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 pub struct Data;
 
@@ -111,7 +112,7 @@ impl Display for Data {
 }
 
 /// QUIT command
-#[derive(PartialEq, Clone, Debug, Copy)]
+#[derive(PartialEq, Eq, Clone, Debug, Copy)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 pub struct Quit;
 
@@ -122,7 +123,7 @@ impl Display for Quit {
 }
 
 /// NOOP command
-#[derive(PartialEq, Clone, Debug, Copy)]
+#[derive(PartialEq, Eq, Clone, Debug, Copy)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 pub struct Noop;
 
@@ -133,7 +134,7 @@ impl Display for Noop {
 }
 
 /// HELP command
-#[derive(PartialEq, Clone, Debug)]
+#[derive(PartialEq, Eq, Clone, Debug)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 pub struct Help {
     argument: Option<String>,
@@ -143,7 +144,7 @@ impl Display for Help {
     fn fmt(&self, f: &mut Formatter<'_>) -> fmt::Result {
         f.write_str("HELP")?;
         if let Some(argument) = &self.argument {
-            write!(f, " {}", argument)?;
+            write!(f, " {argument}")?;
         }
         f.write_str("\r\n")
     }
@@ -157,7 +158,7 @@ impl Help {
 }
 
 /// VRFY command
-#[derive(PartialEq, Clone, Debug)]
+#[derive(PartialEq, Eq, Clone, Debug)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 pub struct Vrfy {
     argument: String,
@@ -177,7 +178,7 @@ impl Vrfy {
 }
 
 /// EXPN command
-#[derive(PartialEq, Clone, Debug)]
+#[derive(PartialEq, Eq, Clone, Debug)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 pub struct Expn {
     argument: String,
@@ -197,7 +198,7 @@ impl Expn {
 }
 
 /// RSET command
-#[derive(PartialEq, Clone, Debug, Copy)]
+#[derive(PartialEq, Eq, Clone, Debug, Copy)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 pub struct Rset;
 
@@ -208,7 +209,7 @@ impl Display for Rset {
 }
 
 /// AUTH command
-#[derive(PartialEq, Clone, Debug)]
+#[derive(PartialEq, Eq, Clone, Debug)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 pub struct Auth {
     mechanism: Mechanism,
@@ -219,7 +220,7 @@ pub struct Auth {
 
 impl Display for Auth {
     fn fmt(&self, f: &mut Formatter<'_>) -> fmt::Result {
-        let encoded_response = self.response.as_ref().map(base64::encode);
+        let encoded_response = self.response.as_ref().map(crate::base64::encode);
 
         if self.mechanism.supports_initial_response() {
             write!(f, "AUTH {} {}", self.mechanism, encoded_response.unwrap())?;
@@ -261,16 +262,17 @@ impl Auth {
         response: &Response,
     ) -> Result<Auth, Error> {
         if !response.has_code(334) {
-            return Err(Error::ResponseParsing("Expecting a challenge"));
+            return Err(error::response("Expecting a challenge"));
         }
 
         let encoded_challenge = response
             .first_word()
-            .ok_or(Error::ResponseParsing("Could not read auth challenge"))?;
+            .ok_or_else(|| error::response("Could not read auth challenge"))?;
         #[cfg(feature = "tracing")]
         tracing::debug!("auth encoded challenge: {}", encoded_challenge);
 
-        let decoded_challenge = String::from_utf8(base64::decode(&encoded_challenge)?)?;
+        let decoded_base64 = crate::base64::decode(encoded_challenge).map_err(error::response)?;
+        let decoded_challenge = String::from_utf8(decoded_base64).map_err(error::response)?;
         #[cfg(feature = "tracing")]
         tracing::debug!("auth decoded challenge: {}", decoded_challenge);
 
@@ -287,21 +289,22 @@ impl Auth {
 
 #[cfg(test)]
 mod test {
+    use std::str::FromStr;
+
     use super::*;
     use crate::transport::smtp::extension::MailBodyParameter;
-    use std::str::FromStr;
 
     #[test]
     fn test_display() {
-        let id = ClientId::Domain("localhost".to_string());
+        let id = ClientId::Domain("localhost".to_owned());
         let email = Address::from_str("test@example.com").unwrap();
         let mail_parameter = MailParameter::Other {
-            keyword: "TEST".to_string(),
-            value: Some("value".to_string()),
+            keyword: "TEST".to_owned(),
+            value: Some("value".to_owned()),
         };
         let rcpt_parameter = RcptParameter::Other {
-            keyword: "TEST".to_string(),
-            value: Some("value".to_string()),
+            keyword: "TEST".to_owned(),
+            value: Some("value".to_owned()),
         };
         assert_eq!(format!("{}", Ehlo::new(id)), "EHLO localhost\r\n");
         assert_eq!(
@@ -338,24 +341,18 @@ mod test {
             format!("{}", Rcpt::new(email, vec![rcpt_parameter])),
             "RCPT TO:<test@example.com> TEST=value\r\n"
         );
-        assert_eq!(format!("{}", Quit), "QUIT\r\n");
-        assert_eq!(format!("{}", Data), "DATA\r\n");
-        assert_eq!(format!("{}", Noop), "NOOP\r\n");
+        assert_eq!(format!("{Quit}"), "QUIT\r\n");
+        assert_eq!(format!("{Data}"), "DATA\r\n");
+        assert_eq!(format!("{Noop}"), "NOOP\r\n");
         assert_eq!(format!("{}", Help::new(None)), "HELP\r\n");
         assert_eq!(
-            format!("{}", Help::new(Some("test".to_string()))),
+            format!("{}", Help::new(Some("test".to_owned()))),
             "HELP test\r\n"
         );
-        assert_eq!(
-            format!("{}", Vrfy::new("test".to_string())),
-            "VRFY test\r\n"
-        );
-        assert_eq!(
-            format!("{}", Expn::new("test".to_string())),
-            "EXPN test\r\n"
-        );
-        assert_eq!(format!("{}", Rset), "RSET\r\n");
-        let credentials = Credentials::new("user".to_string(), "password".to_string());
+        assert_eq!(format!("{}", Vrfy::new("test".to_owned())), "VRFY test\r\n");
+        assert_eq!(format!("{}", Expn::new("test".to_owned())), "EXPN test\r\n");
+        assert_eq!(format!("{Rset}"), "RSET\r\n");
+        let credentials = Credentials::new("user".to_owned(), "password".to_owned());
         assert_eq!(
             format!(
                 "{}",

src/transport/smtp/connection_url.rs

@@ -0,0 +1,131 @@
+use std::borrow::Cow;
+
+use url::Url;
+
+#[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+use super::client::{Tls, TlsParameters};
+#[cfg(any(feature = "tokio1", feature = "async-std1"))]
+use super::AsyncSmtpTransportBuilder;
+use super::{
+    authentication::Credentials, error, extension::ClientId, Error, SmtpTransportBuilder,
+    SMTP_PORT, SUBMISSIONS_PORT, SUBMISSION_PORT,
+};
+
+pub(crate) trait TransportBuilder {
+    fn new<T: Into<String>>(server: T) -> Self;
+    fn tls(self, tls: super::Tls) -> Self;
+    fn port(self, port: u16) -> Self;
+    fn credentials(self, credentials: Credentials) -> Self;
+    fn hello_name(self, name: ClientId) -> Self;
+}
+
+impl TransportBuilder for SmtpTransportBuilder {
+    fn new<T: Into<String>>(server: T) -> Self {
+        Self::new(server)
+    }
+
+    fn tls(self, tls: super::Tls) -> Self {
+        self.tls(tls)
+    }
+
+    fn port(self, port: u16) -> Self {
+        self.port(port)
+    }
+
+    fn credentials(self, credentials: Credentials) -> Self {
+        self.credentials(credentials)
+    }
+
+    fn hello_name(self, name: ClientId) -> Self {
+        self.hello_name(name)
+    }
+}
+
+#[cfg(any(feature = "tokio1", feature = "async-std1"))]
+impl TransportBuilder for AsyncSmtpTransportBuilder {
+    fn new<T: Into<String>>(server: T) -> Self {
+        Self::new(server)
+    }
+
+    fn tls(self, tls: super::Tls) -> Self {
+        self.tls(tls)
+    }
+
+    fn port(self, port: u16) -> Self {
+        self.port(port)
+    }
+
+    fn credentials(self, credentials: Credentials) -> Self {
+        self.credentials(credentials)
+    }
+
+    fn hello_name(self, name: ClientId) -> Self {
+        self.hello_name(name)
+    }
+}
+
+/// Create a new `SmtpTransportBuilder` or `AsyncSmtpTransportBuilder` from a connection URL
+pub(crate) fn from_connection_url<B: TransportBuilder>(connection_url: &str) -> Result<B, Error> {
+    let connection_url = Url::parse(connection_url).map_err(error::connection)?;
+    let tls: Option<String> = connection_url
+        .query_pairs()
+        .find(|(k, _)| k == "tls")
+        .map(|(_, v)| v.to_string());
+
+    let host = connection_url
+        .host_str()
+        .ok_or_else(|| error::connection("smtp host undefined"))?;
+
+    let mut builder = B::new(host);
+
+    match (connection_url.scheme(), tls.as_deref()) {
+        ("smtp", None) => {
+            builder = builder.port(connection_url.port().unwrap_or(SMTP_PORT));
+        }
+        #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+        ("smtp", Some("required")) => {
+            builder = builder
+                .port(connection_url.port().unwrap_or(SUBMISSION_PORT))
+                .tls(Tls::Required(TlsParameters::new(host.into())?));
+        }
+        #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+        ("smtp", Some("opportunistic")) => {
+            builder = builder
+                .port(connection_url.port().unwrap_or(SUBMISSION_PORT))
+                .tls(Tls::Opportunistic(TlsParameters::new(host.into())?));
+        }
+        #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+        ("smtps", _) => {
+            builder = builder
+                .port(connection_url.port().unwrap_or(SUBMISSIONS_PORT))
+                .tls(Tls::Wrapper(TlsParameters::new(host.into())?));
+        }
+        (scheme, tls) => {
+            return Err(error::connection(format!(
+                "Unknown scheme '{scheme}' or tls parameter '{tls:?}', note that a transport with TLS requires one of the TLS features"
+            )))
+        }
+    }
+
+    // use the path segment of the URL as name in the name in the HELO / EHLO command
+    if connection_url.path().len() > 1 {
+        let name = connection_url.path().trim_matches('/').to_owned();
+        builder = builder.hello_name(ClientId::Domain(name));
+    }
+
+    if let Some(password) = connection_url.password() {
+        let percent_decode = |s: &str| {
+            percent_encoding::percent_decode_str(s)
+                .decode_utf8()
+                .map(Cow::into_owned)
+                .map_err(error::connection)
+        };
+        let credentials = Credentials::new(
+            percent_decode(connection_url.username())?,
+            percent_decode(password)?,
+        );
+        builder = builder.credentials(credentials);
+    }
+
+    Ok(builder)
+}

src/transport/smtp/error.rs

@@ -1,162 +1,203 @@
 //! Error and result type for SMTP clients
 
-use self::Error::*;
-use crate::transport::smtp::response::{Response, Severity};
-use base64::DecodeError;
-use std::{
-    error::Error as StdError,
-    fmt::{self, Display, Formatter},
-    io,
-    string::FromUtf8Error,
+use std::{error::Error as StdError, fmt};
+
+use crate::{
+    transport::smtp::response::{Code, Severity},
+    BoxError,
 };
 
-/// An enum of all error kinds.
-#[derive(Debug)]
-pub enum Error {
-    /// Transient SMTP error, 4xx reply code
-    ///
-    /// [RFC 5321, section 4.2.1](https://tools.ietf.org/html/rfc5321#section-4.2.1)
-    Transient(Response),
-    /// Permanent SMTP error, 5xx reply code
-    ///
-    /// [RFC 5321, section 4.2.1](https://tools.ietf.org/html/rfc5321#section-4.2.1)
-    Permanent(Response),
-    /// Error parsing a response
-    ResponseParsing(&'static str),
-    /// Error parsing a base64 string in response
-    ChallengeParsing(DecodeError),
-    /// Error parsing UTF8 in response
-    Utf8Parsing(FromUtf8Error),
-    /// Internal client error
-    Client(&'static str),
-    /// DNS resolution error
-    Resolution,
-    /// IO error
-    Io(io::Error),
-    /// TLS error
-    #[cfg(feature = "native-tls")]
-    #[cfg_attr(docsrs, doc(cfg(feature = "native-tls")))]
-    Tls(native_tls::Error),
-    /// Parsing error
-    Parsing(nom::error::ErrorKind),
-    /// Invalid hostname
-    #[cfg(feature = "rustls-tls")]
-    #[cfg_attr(docsrs, doc(cfg(feature = "rustls-tls")))]
-    InvalidDNSName(webpki::InvalidDNSNameError),
-    #[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
-    #[cfg_attr(docsrs, doc(cfg(any(feature = "native-tls", feature = "rustls-tls"))))]
-    InvalidCertificate,
-    #[cfg(feature = "r2d2")]
-    #[cfg_attr(docsrs, doc(cfg(feature = "r2d2")))]
-    Pool(r2d2::Error),
+// Inspired by https://github.com/seanmonstar/reqwest/blob/a8566383168c0ef06c21f38cbc9213af6ff6db31/src/error.rs
+
+/// The Errors that may occur when sending an email over SMTP
+pub struct Error {
+    inner: Box<Inner>,
 }
 
-impl Display for Error {
-    fn fmt(&self, fmt: &mut Formatter<'_>) -> Result<(), fmt::Error> {
-        match *self {
-            // Try to display the first line of the server's response that usually
-            // contains a short humanly readable error message
-            Transient(ref err) => fmt.write_str(
-                err.first_line()
-                    .unwrap_or("transient error during SMTP transaction"),
-            ),
-            Permanent(ref err) => fmt.write_str(
-                err.first_line()
-                    .unwrap_or("permanent error during SMTP transaction"),
-            ),
-            ResponseParsing(err) => fmt.write_str(err),
-            ChallengeParsing(ref err) => err.fmt(fmt),
-            Utf8Parsing(ref err) => err.fmt(fmt),
-            Resolution => fmt.write_str("could not resolve hostname"),
-            Client(err) => fmt.write_str(err),
-            Io(ref err) => err.fmt(fmt),
-            #[cfg(feature = "native-tls")]
-            Tls(ref err) => err.fmt(fmt),
-            Parsing(ref err) => fmt.write_str(err.description()),
-            #[cfg(feature = "rustls-tls")]
-            InvalidDNSName(ref err) => err.fmt(fmt),
-            #[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
-            InvalidCertificate => fmt.write_str("invalid certificate"),
-            #[cfg(feature = "r2d2")]
-            Pool(ref err) => err.fmt(fmt),
+struct Inner {
+    kind: Kind,
+    source: Option<BoxError>,
+}
+
+impl Error {
+    pub(crate) fn new<E>(kind: Kind, source: Option<E>) -> Error
+    where
+        E: Into<BoxError>,
+    {
+        Error {
+            inner: Box::new(Inner {
+                kind,
+                source: source.map(Into::into),
+            }),
         }
     }
-}
 
-impl StdError for Error {
-    fn source(&self) -> Option<&(dyn StdError + 'static)> {
-        match *self {
-            ChallengeParsing(ref err) => Some(&*err),
-            Utf8Parsing(ref err) => Some(&*err),
-            Io(ref err) => Some(&*err),
-            #[cfg(feature = "native-tls")]
-            Tls(ref err) => Some(&*err),
+    /// Returns true if the error is from response
+    pub fn is_response(&self) -> bool {
+        matches!(self.inner.kind, Kind::Response)
+    }
+
+    /// Returns true if the error is from client
+    pub fn is_client(&self) -> bool {
+        matches!(self.inner.kind, Kind::Client)
+    }
+
+    /// Returns true if the error is a transient SMTP error
+    pub fn is_transient(&self) -> bool {
+        matches!(self.inner.kind, Kind::Transient(_))
+    }
+
+    /// Returns true if the error is a permanent SMTP error
+    pub fn is_permanent(&self) -> bool {
+        matches!(self.inner.kind, Kind::Permanent(_))
+    }
+
+    /// Returns true if the error is caused by a timeout
+    pub fn is_timeout(&self) -> bool {
+        let mut source = self.source();
+
+        while let Some(err) = source {
+            if let Some(io_err) = err.downcast_ref::<std::io::Error>() {
+                return io_err.kind() == std::io::ErrorKind::TimedOut;
+            }
+
+            source = err.source();
+        }
+
+        false
+    }
+
+    /// Returns true if the error is from TLS
+    #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+    #[cfg_attr(
+        docsrs,
+        doc(cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls")))
+    )]
+    pub fn is_tls(&self) -> bool {
+        matches!(self.inner.kind, Kind::Tls)
+    }
+
+    /// Returns true if the error is because the transport was shut down
+    pub fn is_transport_shutdown(&self) -> bool {
+        matches!(self.inner.kind, Kind::TransportShutdown)
+    }
+
+    /// Returns the status code, if the error was generated from a response.
+    pub fn status(&self) -> Option<Code> {
+        match self.inner.kind {
+            Kind::Transient(code) | Kind::Permanent(code) => Some(code),
             _ => None,
         }
     }
 }
 
-impl From<io::Error> for Error {
-    fn from(err: io::Error) -> Error {
-        Io(err)
+#[derive(Debug)]
+pub(crate) enum Kind {
+    /// Transient SMTP error, 4xx reply code
+    ///
+    /// [RFC 5321, section 4.2.1](https://tools.ietf.org/html/rfc5321#section-4.2.1)
+    Transient(Code),
+    /// Permanent SMTP error, 5xx reply code
+    ///
+    /// [RFC 5321, section 4.2.1](https://tools.ietf.org/html/rfc5321#section-4.2.1)
+    Permanent(Code),
+    /// Error parsing a response
+    Response,
+    /// Internal client error
+    Client,
+    /// Connection error
+    Connection,
+    /// Underlying network i/o error
+    Network,
+    /// TLS error
+    #[cfg_attr(
+        docsrs,
+        doc(cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls")))
+    )]
+    #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+    Tls,
+    /// Transport shutdown error
+    TransportShutdown,
+}
+
+impl fmt::Debug for Error {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        let mut builder = f.debug_struct("lettre::transport::smtp::Error");
+
+        builder.field("kind", &self.inner.kind);
+
+        if let Some(source) = &self.inner.source {
+            builder.field("source", source);
+        }
+
+        builder.finish()
     }
 }
 
-#[cfg(feature = "native-tls")]
-impl From<native_tls::Error> for Error {
-    fn from(err: native_tls::Error) -> Error {
-        Tls(err)
+impl fmt::Display for Error {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        match &self.inner.kind {
+            Kind::Response => f.write_str("response error")?,
+            Kind::Client => f.write_str("internal client error")?,
+            Kind::Network => f.write_str("network error")?,
+            Kind::Connection => f.write_str("Connection error")?,
+            #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+            Kind::Tls => f.write_str("tls error")?,
+            Kind::TransportShutdown => f.write_str("transport has been shut down")?,
+            Kind::Transient(code) => {
+                write!(f, "transient error ({code})")?;
+            }
+            Kind::Permanent(code) => {
+                write!(f, "permanent error ({code})")?;
+            }
+        }
+
+        if let Some(e) = &self.inner.source {
+            write!(f, ": {e}")?;
+        }
+
+        Ok(())
     }
 }
 
-impl From<nom::Err<nom::error::Error<&str>>> for Error {
-    fn from(err: nom::Err<nom::error::Error<&str>>) -> Error {
-        Parsing(match err {
-            nom::Err::Incomplete(_) => nom::error::ErrorKind::Complete,
-            nom::Err::Failure(e) => e.code,
-            nom::Err::Error(e) => e.code,
+impl StdError for Error {
+    fn source(&self) -> Option<&(dyn StdError + 'static)> {
+        self.inner.source.as_ref().map(|e| {
+            let r: &(dyn std::error::Error + 'static) = &**e;
+            r
         })
     }
 }
 
-impl From<DecodeError> for Error {
-    fn from(err: DecodeError) -> Error {
-        ChallengeParsing(err)
+pub(crate) fn code(c: Code, s: Option<String>) -> Error {
+    match c.severity {
+        Severity::TransientNegativeCompletion => Error::new(Kind::Transient(c), s),
+        Severity::PermanentNegativeCompletion => Error::new(Kind::Permanent(c), s),
+        _ => client("Unknown error code"),
     }
 }
 
-impl From<FromUtf8Error> for Error {
-    fn from(err: FromUtf8Error) -> Error {
-        Utf8Parsing(err)
-    }
+pub(crate) fn response<E: Into<BoxError>>(e: E) -> Error {
+    Error::new(Kind::Response, Some(e))
 }
 
-#[cfg(feature = "rustls-tls")]
-impl From<webpki::InvalidDNSNameError> for Error {
-    fn from(err: webpki::InvalidDNSNameError) -> Error {
-        InvalidDNSName(err)
-    }
+pub(crate) fn client<E: Into<BoxError>>(e: E) -> Error {
+    Error::new(Kind::Client, Some(e))
 }
 
-#[cfg(feature = "r2d2")]
-impl From<r2d2::Error> for Error {
-    fn from(err: r2d2::Error) -> Error {
-        Pool(err)
-    }
+pub(crate) fn network<E: Into<BoxError>>(e: E) -> Error {
+    Error::new(Kind::Network, Some(e))
 }
 
-impl From<Response> for Error {
-    fn from(response: Response) -> Error {
-        match response.code.severity {
-            Severity::TransientNegativeCompletion => Transient(response),
-            Severity::PermanentNegativeCompletion => Permanent(response),
-            _ => Client("Unknown error code"),
-        }
-    }
+pub(crate) fn connection<E: Into<BoxError>>(e: E) -> Error {
+    Error::new(Kind::Connection, Some(e))
 }
 
-impl From<&'static str> for Error {
-    fn from(string: &'static str) -> Error {
-        Client(string)
-    }
+#[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+pub(crate) fn tls<E: Into<BoxError>>(e: E) -> Error {
+    Error::new(Kind::Tls, Some(e))
+}
+
+pub(crate) fn transport_shutdown() -> Error {
+    Error::new::<BoxError>(Kind::TransportShutdown, None)
 }

src/transport/smtp/extension.rs

@@ -1,13 +1,16 @@
 //! ESMTP features
 
-use crate::transport::smtp::{
-    authentication::Mechanism, error::Error, response::Response, util::XText,
-};
 use std::{
     collections::HashSet,
     fmt::{self, Display, Formatter},
     net::{Ipv4Addr, Ipv6Addr},
-    result::Result,
+};
+
+use crate::transport::smtp::{
+    authentication::Mechanism,
+    error::{self, Error},
+    response::Response,
+    util::XText,
 };
 
 /// Client identifier, the parameter to `EHLO`
@@ -49,15 +52,16 @@ impl Default for ClientId {
 
 impl Display for ClientId {
     fn fmt(&self, f: &mut Formatter<'_>) -> fmt::Result {
-        match *self {
-            Self::Domain(ref value) => f.write_str(value),
-            Self::Ipv4(ref value) => write!(f, "[{}]", value),
-            Self::Ipv6(ref value) => write!(f, "[IPv6:{}]", value),
+        match self {
+            Self::Domain(value) => f.write_str(value),
+            Self::Ipv4(value) => write!(f, "[{value}]"),
+            Self::Ipv6(value) => write!(f, "[IPv6:{value}]"),
         }
     }
 }
 
 impl ClientId {
+    #[doc(hidden)]
     #[deprecated(since = "0.10.0", note = "Please use ClientId::Domain(domain) instead")]
     /// Creates a new `ClientId` from a fully qualified domain name
     pub fn new(domain: String) -> Self {
@@ -68,18 +72,19 @@ impl ClientId {
 /// Supported ESMTP keywords
 #[derive(PartialEq, Eq, Hash, Copy, Clone, Debug)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
+#[non_exhaustive]
 pub enum Extension {
     /// 8BITMIME keyword
     ///
-    /// RFC 6152: https://tools.ietf.org/html/rfc6152
+    /// Defined in [RFC 6152](https://tools.ietf.org/html/rfc6152)
     EightBitMime,
     /// SMTPUTF8 keyword
     ///
-    /// RFC 6531: https://tools.ietf.org/html/rfc6531
+    /// Defined in [RFC 6531](https://tools.ietf.org/html/rfc6531)
     SmtpUtfEight,
     /// STARTTLS keyword
     ///
-    /// RFC 2487: https://tools.ietf.org/html/rfc2487
+    /// Defined in [RFC 2487](https://tools.ietf.org/html/rfc2487)
     StartTls,
     /// AUTH mechanism
     Authentication(Mechanism),
@@ -87,11 +92,11 @@ pub enum Extension {
 
 impl Display for Extension {
     fn fmt(&self, f: &mut Formatter<'_>) -> fmt::Result {
-        match *self {
+        match self {
             Extension::EightBitMime => f.write_str("8BITMIME"),
             Extension::SmtpUtfEight => f.write_str("SMTPUTF8"),
             Extension::StartTls => f.write_str("STARTTLS"),
-            Extension::Authentication(ref mechanism) => write!(f, "AUTH {}", mechanism),
+            Extension::Authentication(mechanism) => write!(f, "AUTH {mechanism}"),
         }
     }
 }
@@ -103,17 +108,17 @@ pub struct ServerInfo {
     /// Server name
     ///
     /// The name given in the server banner
-    pub name: String,
+    name: String,
     /// ESMTP features supported by the server
     ///
     /// It contains the features supported by the server and known by the `Extension` module.
-    pub features: HashSet<Extension>,
+    features: HashSet<Extension>,
 }
 
 impl Display for ServerInfo {
     fn fmt(&self, f: &mut Formatter<'_>) -> fmt::Result {
         let features = if self.features.is_empty() {
-            "no supported features".to_string()
+            "no supported features".to_owned()
         } else {
             format!("{:?}", self.features)
         };
@@ -124,14 +129,13 @@ impl Display for ServerInfo {
 impl ServerInfo {
     /// Parses a EHLO response to create a `ServerInfo`
     pub fn from_response(response: &Response) -> Result<ServerInfo, Error> {
-        let name = match response.first_word() {
-            Some(name) => name,
-            None => return Err(Error::ResponseParsing("Could not read server name")),
+        let Some(name) = response.first_word() else {
+            return Err(error::response("Could not read server name"));
         };
 
         let mut features: HashSet<Extension> = HashSet::new();
 
-        for line in response.message.as_slice() {
+        for line in response.message() {
             if line.is_empty() {
                 continue;
             }
@@ -164,11 +168,11 @@ impl ServerInfo {
                     }
                 }
                 _ => (),
-            };
+            }
         }
 
         Ok(ServerInfo {
-            name: name.to_string(),
+            name: name.to_owned(),
             features,
         })
     }
@@ -184,7 +188,7 @@ impl ServerInfo {
             .contains(&Extension::Authentication(mechanism))
     }
 
-    /// Gets a compatible mechanism from list
+    /// Gets a compatible mechanism from a list
     pub fn get_auth_mechanism(&self, mechanisms: &[Mechanism]) -> Option<Mechanism> {
         for mechanism in mechanisms {
             if self.supports_auth_mechanism(*mechanism) {
@@ -193,6 +197,11 @@ impl ServerInfo {
         }
         None
     }
+
+    /// The name given in the server banner
+    pub fn name(&self) -> &str {
+        self.name.as_ref()
+    }
 }
 
 /// A `MAIL FROM` extension parameter
@@ -216,16 +225,16 @@ pub enum MailParameter {
 
 impl Display for MailParameter {
     fn fmt(&self, f: &mut Formatter<'_>) -> fmt::Result {
-        match *self {
-            MailParameter::Body(ref value) => write!(f, "BODY={}", value),
-            MailParameter::Size(size) => write!(f, "SIZE={}", size),
+        match self {
+            MailParameter::Body(value) => write!(f, "BODY={value}"),
+            MailParameter::Size(size) => write!(f, "SIZE={size}"),
             MailParameter::SmtpUtfEight => f.write_str("SMTPUTF8"),
             MailParameter::Other {
-                ref keyword,
-                value: Some(ref value),
+                keyword,
+                value: Some(value),
             } => write!(f, "{}={}", keyword, XText(value)),
             MailParameter::Other {
-                ref keyword,
+                keyword,
                 value: None,
             } => f.write_str(keyword),
         }
@@ -266,13 +275,13 @@ pub enum RcptParameter {
 
 impl Display for RcptParameter {
     fn fmt(&self, f: &mut Formatter<'_>) -> fmt::Result {
-        match *self {
+        match &self {
             RcptParameter::Other {
-                ref keyword,
-                value: Some(ref value),
-            } => write!(f, "{}={}", keyword, XText(value)),
+                keyword,
+                value: Some(value),
+            } => write!(f, "{keyword}={}", XText(value)),
             RcptParameter::Other {
-                ref keyword,
+                keyword,
                 value: None,
             } => f.write_str(keyword),
         }
@@ -281,32 +290,27 @@ impl Display for RcptParameter {
 
 #[cfg(test)]
 mod test {
-
     use super::*;
-    use crate::transport::smtp::{
-        authentication::Mechanism,
-        response::{Category, Code, Detail, Response, Severity},
-    };
-    use std::collections::HashSet;
+    use crate::transport::smtp::response::{Category, Code, Detail, Severity};
 
     #[test]
     fn test_clientid_fmt() {
         assert_eq!(
-            format!("{}", ClientId::Domain("test".to_string())),
-            "test".to_string()
+            format!("{}", ClientId::Domain("test".to_owned())),
+            "test".to_owned()
         );
-        assert_eq!(format!("{}", LOCALHOST_CLIENT), "[127.0.0.1]".to_string());
+        assert_eq!(format!("{LOCALHOST_CLIENT}"), "[127.0.0.1]".to_owned());
     }
 
     #[test]
     fn test_extension_fmt() {
         assert_eq!(
             format!("{}", Extension::EightBitMime),
-            "8BITMIME".to_string()
+            "8BITMIME".to_owned()
         );
         assert_eq!(
             format!("{}", Extension::Authentication(Mechanism::Plain)),
-            "AUTH PLAIN".to_string()
+            "AUTH PLAIN".to_owned()
         );
     }
 
@@ -319,11 +323,11 @@ mod test {
             format!(
                 "{}",
                 ServerInfo {
-                    name: "name".to_string(),
+                    name: "name".to_owned(),
                     features: eightbitmime,
                 }
             ),
-            "name with {EightBitMime}".to_string()
+            "name with {EightBitMime}".to_owned()
         );
 
         let empty = HashSet::new();
@@ -332,11 +336,11 @@ mod test {
             format!(
                 "{}",
                 ServerInfo {
-                    name: "name".to_string(),
+                    name: "name".to_owned(),
                     features: empty,
                 }
             ),
-            "name with no supported features".to_string()
+            "name with no supported features".to_owned()
         );
 
         let mut plain = HashSet::new();
@@ -346,11 +350,11 @@ mod test {
             format!(
                 "{}",
                 ServerInfo {
-                    name: "name".to_string(),
+                    name: "name".to_owned(),
                     features: plain,
                 }
             ),
-            "name with {Authentication(Plain)}".to_string()
+            "name with {Authentication(Plain)}".to_owned()
         );
     }
 
@@ -362,18 +366,14 @@ mod test {
                 Category::Unspecified4,
                 Detail::One,
             ),
-            vec![
-                "me".to_string(),
-                "8BITMIME".to_string(),
-                "SIZE 42".to_string(),
-            ],
+            vec!["me".to_owned(), "8BITMIME".to_owned(), "SIZE 42".to_owned()],
         );
 
         let mut features = HashSet::new();
         assert!(features.insert(Extension::EightBitMime));
 
         let server_info = ServerInfo {
-            name: "me".to_string(),
+            name: "me".to_owned(),
             features,
         };
 
@@ -389,10 +389,10 @@ mod test {
                 Detail::One,
             ),
             vec![
-                "me".to_string(),
-                "AUTH PLAIN CRAM-MD5 XOAUTH2 OTHER".to_string(),
-                "8BITMIME".to_string(),
-                "SIZE 42".to_string(),
+                "me".to_owned(),
+                "AUTH PLAIN CRAM-MD5 XOAUTH2 OTHER".to_owned(),
+                "8BITMIME".to_owned(),
+                "SIZE 42".to_owned(),
             ],
         );
 
@@ -402,7 +402,7 @@ mod test {
         assert!(features2.insert(Extension::Authentication(Mechanism::Xoauth2),));
 
         let server_info2 = ServerInfo {
-            name: "me".to_string(),
+            name: "me".to_owned(),
             features: features2,
         };
 

src/transport/smtp/mod.rs

@@ -26,153 +26,180 @@
 //!
 //! The relay server can be the local email server, a specific host or a third-party service.
 //!
-//! #### Simple example
+//! #### Simple example with authentication
 //!
-//! This is the most basic example of usage:
+//! A good starting point for sending emails via SMTP relay is to
+//! do the following:
 //!
 //! ```rust,no_run
-//! # #[cfg(all(feature = "builder", any(feature = "native-tls", feature = "rustls-tls")))]
+//! # #[cfg(all(feature = "builder", any(feature = "native-tls", feature = "rustls")))]
 //! # fn test() -> Result<(), Box<dyn std::error::Error>> {
-//! use lettre::{Message, Transport, SmtpTransport};
+//! use lettre::{
+//!     message::header::ContentType,
+//!     transport::smtp::authentication::{Credentials, Mechanism},
+//!     Message, SmtpTransport, Transport,
+//! };
 //!
 //! let email = Message::builder()
 //!     .from("NoBody <nobody@domain.tld>".parse()?)
 //!     .reply_to("Yuin <yuin@domain.tld>".parse()?)
 //!     .to("Hei <hei@domain.tld>".parse()?)
 //!     .subject("Happy new year")
+//!     .header(ContentType::TEXT_PLAIN)
 //!     .body(String::from("Be happy!"))?;
 //!
-//! // Create TLS transport on port 465
-//! let sender = SmtpTransport::relay("smtp.example.com")
-//!     .expect("relay valid")
+//! // Create the SMTPS transport
+//! let sender = SmtpTransport::relay("smtp.example.com")?
+//!     // Add credentials for authentication
+//!     .credentials(Credentials::new(
+//!         "username".to_owned(),
+//!         "password".to_owned(),
+//!     ))
+//!     // Optionally configure expected authentication mechanism
+//!     .authentication(vec![Mechanism::Plain])
 //!     .build();
+//!
 //! // Send the email via remote relay
-//! let result = sender.send(&email);
-//! assert!(result.is_ok());
+//! sender.send(&email)?;
 //! # Ok(())
 //! # }
 //! ```
-
-//! #### Complete example
 //!
-//! ```todo
-//! # #[cfg(feature = "smtp-transport")]
-//! # {
-//! use lettre::transport::smtp::authentication::{Credentials, Mechanism};
-//! use lettre::{Email, Envelope, Transport, SmtpClient};
-//! use lettre::transport::smtp::extension::ClientId;
+//! #### Shortening configuration
 //!
-//! let email_1 = Email::new(
-//!     Envelope::new(
-//!         Some(EmailAddress::new("user@localhost".to_string())?),
-//!         vec![EmailAddress::new("root@localhost".to_string())?],
-//!     )?,
-//!     "id1".to_string(),
-//!     "Hello world".to_string().into_bytes(),
-//! );
+//! It can be very repetitive to ask the user for every SMTP connection parameter.
+//! In some cases this can be simplified by using a connection URI instead.
 //!
-//! let email_2 = Email::new(
-//!     Envelope::new(
-//!         Some(EmailAddress::new("user@localhost".to_string())?),
-//!         vec![EmailAddress::new("root@localhost".to_string())?],
-//!     )?,
-//!     "id2".to_string(),
-//!     "Hello world a second time".to_string().into_bytes(),
-//! );
+//! For more information take a look at [`SmtpTransport::from_url`] or [`AsyncSmtpTransport::from_url`].
 //!
-//! // Connect to a remote server on a custom port
-//! let mut mailer = SmtpClient::new_simple("server.tld")?
-//!    // Set the name sent during EHLO/HELO, default is `localhost`
-//!    .hello_name(ClientId::Domain("my.hostname.tld".to_string()))
-//!    // Add credentials for authentication
-//!    .credentials(Credentials::new("username".to_string(), "password".to_string()))
-//!    // Enable SMTPUTF8 if the server supports it
-//!    .smtp_utf8(true)
-//!    // Configure expected authentication mechanism
-//!    .authentication_mechanism(Mechanism::Plain)
-//!    // Enable connection reuse
-//!    .connection_reuse(ConnectionReuseParameters::ReuseUnlimited).transport();
-//!
-//! let result_1 = mailer.send(&email_1);
-//! assert!(result_1.is_ok());
-//!
-//! // The second email will use the same connection
-//! let result_2 = mailer.send(&email_2);
-//! assert!(result_2.is_ok());
-//!
-//! // Explicitly close the SMTP transaction as we enabled connection reuse
-//! mailer.close();
-//! # }
-//! ```
-//!
-//! You can specify custom TLS settings:
-//!
-//! ```todo
-//! # #[cfg(feature = "native-tls")]
-//! # {
+//! ```rust,no_run
+//! # #[cfg(all(feature = "builder", any(feature = "native-tls", feature = "rustls")))]
+//! # fn test() -> Result<(), Box<dyn std::error::Error>> {
 //! use lettre::{
-//!     ClientSecurity, ClientTlsParameters, EmailAddress, Envelope,
-//!     Email, SmtpClient, Transport,
+//!     message::header::ContentType,
+//!     transport::smtp::authentication::{Credentials, Mechanism},
+//!     Message, SmtpTransport, Transport,
 //! };
-//! use lettre::transport::smtp::authentication::{Credentials, Mechanism};
-//! use lettre::transport::smtp::ConnectionReuseParameters;
-//! use native_tls::{Protocol, TlsConnector};
 //!
-//!     let email = Email::new(
-//!         Envelope::new(
-//!             Some(EmailAddress::new("user@localhost".to_string())?),
-//!             vec![EmailAddress::new("root@localhost".to_string())?],
-//!         )?,
-//!         "message_id".to_string(),
-//!         "Hello world".to_string().into_bytes(),
-//!     );
+//! let email = Message::builder()
+//!     .from("NoBody <nobody@domain.tld>".parse()?)
+//!     .reply_to("Yuin <yuin@domain.tld>".parse()?)
+//!     .to("Hei <hei@domain.tld>".parse()?)
+//!     .subject("Happy new year")
+//!     .header(ContentType::TEXT_PLAIN)
+//!     .body(String::from("Be happy!"))?;
 //!
-//!     let mut tls_builder = TlsConnector::builder();
-//!     tls_builder.min_protocol_version(Some(Protocol::Tlsv10));
-//!     let tls_parameters =
-//!         ClientTlsParameters::new(
-//!             "smtp.example.com".to_string(),
-//!             tls_builder.build()?
-//!         );
+//! // Create the SMTPS transport
+//! let sender = SmtpTransport::from_url("smtps://username:password@smtp.example.com")?.build();
 //!
-//!     let mut mailer = SmtpClient::new(
-//!         ("smtp.example.com", 465), ClientSecurity::Wrapper(tls_parameters)
-//!     )?
-//!         .authentication_mechanism(Mechanism::Login)
-//!         .credentials(Credentials::new(
-//!             "example_username".to_string(), "example_password".to_string()
-//!         ))
-//!         .connection_reuse(ConnectionReuseParameters::ReuseUnlimited)
-//!         .transport();
-//!
-//!     let result = mailer.send(&email);
-//!
-//!     assert!(result.is_ok());
-//!
-//!     mailer.close();
+//! // Send the email via remote relay
+//! sender.send(&email)?;
+//! # Ok(())
 //! # }
 //! ```
 //!
+//! #### Advanced configuration with custom TLS settings
+//!
+//! ```rust,no_run
+//! # #[cfg(all(feature = "builder", any(feature = "native-tls", feature = "rustls")))]
+//! # fn test() -> Result<(), Box<dyn std::error::Error>> {
+//! use std::fs;
+//!
+//! use lettre::{
+//!     message::header::ContentType,
+//!     transport::smtp::client::{Certificate, Tls, TlsParameters},
+//!     Message, SmtpTransport, Transport,
+//! };
+//!
+//! let email = Message::builder()
+//!     .from("NoBody <nobody@domain.tld>".parse()?)
+//!     .reply_to("Yuin <yuin@domain.tld>".parse()?)
+//!     .to("Hei <hei@domain.tld>".parse()?)
+//!     .subject("Happy new year")
+//!     .header(ContentType::TEXT_PLAIN)
+//!     .body(String::from("Be happy!"))?;
+//!
+//! // Custom TLS configuration - Use a self signed certificate
+//! let cert = fs::read("self-signed.crt")?;
+//! let cert = Certificate::from_pem(&cert)?;
+//! let tls = TlsParameters::builder(/* TLS SNI value */ "smtp.example.com".to_owned())
+//!     .add_root_certificate(cert)
+//!     .build()?;
+//!
+//! // Create the SMTPS transport
+//! let sender = SmtpTransport::relay("smtp.example.com")?
+//!     .tls(Tls::Wrapper(tls))
+//!     .build();
+//!
+//! // Send the email via remote relay
+//! sender.send(&email)?;
+//! # Ok(())
+//! # }
+//! ```
+//!
+//! #### Connection pooling
+//!
+//! [`SmtpTransport`] and [`AsyncSmtpTransport`] store connections in
+//! a connection pool by default. This avoids connecting and disconnecting
+//! from the relay server for every message the application tries to send. For the connection pool
+//! to work the instance of the transport **must** be reused.
+//! In a webserver context it may go about this:
+//!
+//! ```rust,no_run
+//! # #[cfg(all(feature = "builder", any(feature = "native-tls", feature = "rustls")))]
+//! # fn test() {
+//! use lettre::{
+//!     message::header::ContentType,
+//!     transport::smtp::{authentication::Credentials, PoolConfig},
+//!     Message, SmtpTransport, Transport,
+//! };
+//! #
+//! # type Result<T> = std::result::Result<T, Box<dyn std::error::Error>>;
+//!
+//! /// The global application state
+//! #[derive(Debug)]
+//! struct AppState {
+//!     smtp: SmtpTransport,
+//!     // ... other global application parameters
+//! }
+//!
+//! impl AppState {
+//!     pub fn new(smtp_url: &str) -> Result<Self> {
+//!         let smtp = SmtpTransport::from_url(smtp_url)?.build();
+//!         Ok(Self { smtp })
+//!     }
+//! }
+//!
+//! fn handle_request(app_state: &AppState) -> Result<String> {
+//!     let email = Message::builder()
+//!         .from("NoBody <nobody@domain.tld>".parse()?)
+//!         .reply_to("Yuin <yuin@domain.tld>".parse()?)
+//!         .to("Hei <hei@domain.tld>".parse()?)
+//!         .subject("Happy new year")
+//!         .header(ContentType::TEXT_PLAIN)
+//!         .body(String::from("Be happy!"))?;
+//!
+//!     // Send the email via remote relay
+//!     app_state.smtp.send(&email)?;
+//!
+//!     Ok("The email has successfully been sent!".to_owned())
+//! }
+//! # }
+//! ```
 
-#[cfg(feature = "async-std1")]
-pub use self::async_transport::AsyncStd1Connector;
-#[cfg(feature = "tokio02")]
-pub use self::async_transport::Tokio02Connector;
-#[cfg(feature = "tokio1")]
-pub use self::async_transport::Tokio1Connector;
-#[cfg(any(feature = "tokio02", feature = "tokio1", feature = "async-std1"))]
-pub use self::async_transport::{
-    AsyncSmtpConnector, AsyncSmtpTransport, AsyncSmtpTransportBuilder,
-};
-#[cfg(feature = "r2d2")]
+use std::time::Duration;
+
+use client::Tls;
+
+#[cfg(any(feature = "tokio1", feature = "async-std1"))]
+pub use self::async_transport::{AsyncSmtpTransport, AsyncSmtpTransportBuilder};
+#[cfg(feature = "pool")]
 pub use self::pool::PoolConfig;
-#[cfg(feature = "r2d2")]
-pub(crate) use self::transport::SmtpClient;
 pub use self::{
     error::Error,
     transport::{SmtpTransport, SmtpTransportBuilder},
 };
-#[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
+#[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
 use crate::transport::smtp::client::TlsParameters;
 use crate::transport::smtp::{
     authentication::{Credentials, Mechanism, DEFAULT_MECHANISMS},
@@ -180,21 +207,20 @@ use crate::transport::smtp::{
     extension::ClientId,
     response::Response,
 };
-use client::Tls;
-use std::time::Duration;
 
-#[cfg(any(feature = "tokio02", feature = "tokio1", feature = "async-std1"))]
+#[cfg(any(feature = "tokio1", feature = "async-std1"))]
 mod async_transport;
 pub mod authentication;
 pub mod client;
 pub mod commands;
+mod connection_url;
 mod error;
 pub mod extension;
-#[cfg(feature = "r2d2")]
+#[cfg(feature = "pool")]
 mod pool;
 pub mod response;
 mod transport;
-pub mod util;
+pub(super) mod util;
 
 // Registered port numbers:
 // https://www.iana.
@@ -206,14 +232,13 @@ pub const SMTP_PORT: u16 = 25;
 pub const SUBMISSION_PORT: u16 = 587;
 /// Default submission over TLS port
 ///
-/// https://tools.ietf.org/html/rfc8314
+/// Defined in [RFC8314](https://tools.ietf.org/html/rfc8314)
 pub const SUBMISSIONS_PORT: u16 = 465;
 
 /// Default timeout
-pub const DEFAULT_TIMEOUT: Duration = Duration::from_secs(60);
+const DEFAULT_TIMEOUT: Duration = Duration::from_secs(60);
 
-#[allow(missing_debug_implementations)]
-#[derive(Clone)]
+#[derive(Debug, Clone)]
 struct SmtpInfo {
     /// Name sent during EHLO
     hello_name: ClientId,
@@ -235,7 +260,7 @@ struct SmtpInfo {
 impl Default for SmtpInfo {
     fn default() -> Self {
         Self {
-            server: "localhost".to_string(),
+            server: "localhost".to_owned(),
             port: SMTP_PORT,
             hello_name: ClientId::default(),
             credentials: None,

src/transport/smtp/pool.rs

@@ -1,90 +0,0 @@
-use std::time::Duration;
-
-use crate::transport::smtp::{client::SmtpConnection, error::Error, SmtpClient};
-
-use r2d2::{ManageConnection, Pool};
-
-/// Configuration for a connection pool
-#[derive(Debug, Clone)]
-#[allow(missing_copy_implementations)]
-#[cfg_attr(docsrs, doc(cfg(feature = "r2d2")))]
-pub struct PoolConfig {
-    min_idle: u32,
-    max_size: u32,
-    connection_timeout: Duration,
-    idle_timeout: Duration,
-}
-
-impl PoolConfig {
-    /// Minimum number of idle connections
-    ///
-    /// Defaults to `0`
-    pub fn min_idle(mut self, min_idle: u32) -> Self {
-        self.min_idle = min_idle;
-        self
-    }
-
-    /// Maximum number of pooled connections
-    ///
-    /// Defaults to `10`
-    pub fn max_size(mut self, max_size: u32) -> Self {
-        self.min_idle = max_size;
-        self
-    }
-
-    /// Connection timeout
-    ///
-    /// Defaults to `30 seconds`
-    pub fn connection_timeout(mut self, connection_timeout: Duration) -> Self {
-        self.connection_timeout = connection_timeout;
-        self
-    }
-
-    /// Connection idle timeout
-    ///
-    /// Defaults to `60 seconds`
-    pub fn idle_timeout(mut self, idle_timeout: Duration) -> Self {
-        self.idle_timeout = idle_timeout;
-        self
-    }
-
-    pub(crate) fn build<C: ManageConnection>(&self, client: C) -> Pool<C> {
-        Pool::builder()
-            .min_idle(Some(self.min_idle))
-            .max_size(self.max_size)
-            .connection_timeout(self.connection_timeout)
-            .idle_timeout(Some(self.idle_timeout))
-            .build_unchecked(client)
-    }
-}
-
-impl Default for PoolConfig {
-    fn default() -> Self {
-        Self {
-            min_idle: 0,
-            max_size: 10,
-            connection_timeout: Duration::from_secs(30),
-            idle_timeout: Duration::from_secs(60),
-        }
-    }
-}
-
-impl ManageConnection for SmtpClient {
-    type Connection = SmtpConnection;
-    type Error = Error;
-
-    fn connect(&self) -> Result<Self::Connection, Error> {
-        self.connection()
-    }
-
-    fn is_valid(&self, conn: &mut Self::Connection) -> Result<(), Error> {
-        if conn.test_connected() {
-            return Ok(());
-        }
-        Err(Error::Client("is not connected anymore"))
-    }
-
-    fn has_broken(&self, conn: &mut Self::Connection) -> bool {
-        conn.has_broken()
-    }
-}

src/transport/smtp/pool/async_impl.rs

@@ -0,0 +1,346 @@
+use std::{
+    fmt::{self, Debug},
+    ops::{Deref, DerefMut},
+    sync::{Arc, OnceLock},
+    time::{Duration, Instant},
+};
+
+use futures_util::{
+    lock::Mutex,
+    stream::{self, StreamExt},
+};
+
+use super::{
+    super::{client::AsyncSmtpConnection, Error},
+    PoolConfig,
+};
+use crate::{
+    executor::SpawnHandle,
+    transport::smtp::{async_transport::AsyncSmtpClient, error},
+    Executor,
+};
+
+pub(crate) struct Pool<E: Executor> {
+    config: PoolConfig,
+    connections: Mutex<Option<Vec<ParkedConnection>>>,
+    client: AsyncSmtpClient<E>,
+    handle: OnceLock<E::Handle>,
+}
+
+struct ParkedConnection {
+    conn: AsyncSmtpConnection,
+    since: Instant,
+}
+
+pub(crate) struct PooledConnection<E: Executor> {
+    conn: Option<AsyncSmtpConnection>,
+    pool: Arc<Pool<E>>,
+}
+
+impl<E: Executor> Pool<E> {
+    pub(crate) fn new(config: PoolConfig, client: AsyncSmtpClient<E>) -> Arc<Self> {
+        let pool = Arc::new(Self {
+            config,
+            connections: Mutex::new(Some(Vec::new())),
+            client,
+            handle: OnceLock::new(),
+        });
+
+        {
+            let pool_ = Arc::clone(&pool);
+
+            let min_idle = pool_.config.min_idle;
+            let idle_timeout = pool_.config.idle_timeout;
+            let pool = Arc::downgrade(&pool_);
+
+            let handle = E::spawn(async move {
+                loop {
+                    #[cfg(feature = "tracing")]
+                    tracing::trace!("running cleanup tasks");
+
+                    match pool.upgrade() {
+                        Some(pool) => {
+                            #[allow(clippy::needless_collect)]
+                            let (count, dropped) = {
+                                let mut connections = pool.connections.lock().await;
+                                let Some(connections) = connections.as_mut() else {
+                                    // The transport was shut down
+                                    return;
+                                };
+
+                                let to_drop = connections
+                                    .iter()
+                                    .enumerate()
+                                    .rev()
+                                    .filter(|(_, conn)| conn.idle_duration() > idle_timeout)
+                                    .map(|(i, _)| i)
+                                    .collect::<Vec<_>>();
+                                let dropped = to_drop
+                                    .into_iter()
+                                    .map(|i| connections.remove(i))
+                                    .collect::<Vec<_>>();
+
+                                (connections.len(), dropped)
+                            };
+
+                            #[cfg(feature = "tracing")]
+                            let mut created = 0;
+                            for _ in count..(min_idle as usize) {
+                                let conn = match pool.client.connection().await {
+                                    Ok(conn) => conn,
+                                    Err(err) => {
+                                        #[cfg(feature = "tracing")]
+                                        tracing::warn!("couldn't create idle connection {}", err);
+                                        #[cfg(not(feature = "tracing"))]
+                                        let _ = err;
+
+                                        break;
+                                    }
+                                };
+
+                                let mut connections = pool.connections.lock().await;
+                                let Some(connections) = connections.as_mut() else {
+                                    // The transport was shut down
+                                    return;
+                                };
+
+                                connections.push(ParkedConnection::park(conn));
+
+                                #[cfg(feature = "tracing")]
+                                {
+                                    created += 1;
+                                }
+                            }
+
+                            #[cfg(feature = "tracing")]
+                            if created > 0 {
+                                tracing::debug!("created {} idle connections", created);
+                            }
+
+                            if !dropped.is_empty() {
+                                #[cfg(feature = "tracing")]
+                                tracing::debug!("dropped {} idle connections", dropped.len());
+
+                                abort_concurrent(dropped.into_iter().map(ParkedConnection::unpark))
+                                    .await;
+                            }
+                        }
+                        None => {
+                            #[cfg(feature = "tracing")]
+                            tracing::warn!(
+                                "breaking out of task - no more references to Pool are available"
+                            );
+                            break;
+                        }
+                    }
+
+                    E::sleep(idle_timeout).await;
+                }
+            });
+            pool_
+                .handle
+                .set(handle)
+                .expect("handle hasn't been set yet");
+        }
+
+        pool
+    }
+
+    pub(crate) async fn shutdown(&self) {
+        let connections = { self.connections.lock().await.take() };
+        if let Some(connections) = connections {
+            stream::iter(connections)
+                .for_each_concurrent(8, |conn| async move {
+                    conn.unpark().abort().await;
+                })
+                .await;
+        }
+
+        if let Some(handle) = self.handle.get() {
+            handle.shutdown().await;
+        }
+    }
+
+    pub(crate) async fn connection(self: &Arc<Self>) -> Result<PooledConnection<E>, Error> {
+        loop {
+            let conn = {
+                let mut connections = self.connections.lock().await;
+                let Some(connections) = connections.as_mut() else {
+                    // The transport was shut down
+                    return Err(error::transport_shutdown());
+                };
+                connections.pop()
+            };
+
+            match conn {
+                Some(conn) => {
+                    let mut conn = conn.unpark();
+
+                    // TODO: handle the client try another connection if this one isn't good
+                    if !conn.test_connected().await {
+                        #[cfg(feature = "tracing")]
+                        tracing::debug!("dropping a broken connection");
+
+                        conn.abort().await;
+                        continue;
+                    }
+
+                    #[cfg(feature = "tracing")]
+                    tracing::debug!("reusing a pooled connection");
+
+                    return Ok(PooledConnection::wrap(conn, Arc::clone(self)));
+                }
+                None => {
+                    #[cfg(feature = "tracing")]
+                    tracing::debug!("creating a new connection");
+
+                    let conn = self.client.connection().await?;
+                    return Ok(PooledConnection::wrap(conn, Arc::clone(self)));
+                }
+            }
+        }
+    }
+
+    async fn recycle(&self, mut conn: AsyncSmtpConnection) {
+        if conn.has_broken() {
+            #[cfg(feature = "tracing")]
+            tracing::debug!("dropping a broken connection instead of recycling it");
+
+            conn.abort().await;
+            drop(conn);
+        } else {
+            #[cfg(feature = "tracing")]
+            tracing::debug!("recycling connection");
+
+            let mut connections_guard = self.connections.lock().await;
+
+            if let Some(connections) = connections_guard.as_mut() {
+                if connections.len() >= self.config.max_size as usize {
+                    drop(connections_guard);
+                    conn.abort().await;
+                } else {
+                    let conn = ParkedConnection::park(conn);
+                    connections.push(conn);
+                }
+            } else {
+                // The pool has already been shut down
+                drop(connections_guard);
+                conn.abort().await;
+            }
+        }
+    }
+}
+
+impl<E: Executor> Debug for Pool<E> {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        f.debug_struct("Pool")
+            .field("config", &self.config)
+            .field(
+                "connections",
+                &match self.connections.try_lock() {
+                    Some(connections) => {
+                        if let Some(connections) = connections.as_ref() {
+                            format!("{} connections", connections.len())
+                        } else {
+                            "SHUT DOWN".to_owned()
+                        }
+                    }
+
+                    None => "LOCKED".to_owned(),
+                },
+            )
+            .field("client", &self.client)
+            .field(
+                "handle",
+                &match self.handle.get() {
+                    Some(_) => "Some(JoinHandle)",
+                    None => "None",
+                },
+            )
+            .finish()
+    }
+}
+
+impl<E: Executor> Drop for Pool<E> {
+    fn drop(&mut self) {
+        #[cfg(feature = "tracing")]
+        tracing::debug!("dropping Pool");
+
+        let connections = self.connections.get_mut().take();
+        let handle = self.handle.take();
+        E::spawn(async move {
+            if let Some(handle) = handle {
+                handle.shutdown().await;
+            }
+
+            if let Some(connections) = connections {
+                abort_concurrent(connections.into_iter().map(ParkedConnection::unpark)).await;
+            }
+        });
+    }
+}
+
+impl ParkedConnection {
+    fn park(conn: AsyncSmtpConnection) -> Self {
+        Self {
+            conn,
+            since: Instant::now(),
+        }
+    }
+
+    fn idle_duration(&self) -> Duration {
+        self.since.elapsed()
+    }
+
+    fn unpark(self) -> AsyncSmtpConnection {
+        self.conn
+    }
+}
+
+impl<E: Executor> PooledConnection<E> {
+    fn wrap(conn: AsyncSmtpConnection, pool: Arc<Pool<E>>) -> Self {
+        Self {
+            conn: Some(conn),
+            pool,
+        }
+    }
+}
+
+impl<E: Executor> Deref for PooledConnection<E> {
+    type Target = AsyncSmtpConnection;
+
+    fn deref(&self) -> &Self::Target {
+        self.conn.as_ref().expect("conn hasn't been dropped yet")
+    }
+}
+
+impl<E: Executor> DerefMut for PooledConnection<E> {
+    fn deref_mut(&mut self) -> &mut Self::Target {
+        self.conn.as_mut().expect("conn hasn't been dropped yet")
+    }
+}
+
+impl<E: Executor> Drop for PooledConnection<E> {
+    fn drop(&mut self) {
+        let conn = self
+            .conn
+            .take()
+            .expect("AsyncSmtpConnection hasn't been taken yet");
+        let pool = Arc::clone(&self.pool);
+
+        E::spawn(async move {
+            pool.recycle(conn).await;
+        });
+    }
+}
+
+async fn abort_concurrent<I>(iter: I)
+where
+    I: Iterator<Item = AsyncSmtpConnection>,
+{
+    stream::iter(iter)
+        .for_each_concurrent(8, |mut conn| async move {
+            conn.abort().await;
+        })
+        .await;
+}

src/transport/smtp/pool/mod.rs

@@ -0,0 +1,66 @@
+use std::time::Duration;
+
+#[cfg(any(feature = "tokio1", feature = "async-std1"))]
+pub(super) mod async_impl;
+pub(super) mod sync_impl;
+
+/// Configuration for a connection pool
+#[derive(Debug, Clone)]
+#[allow(missing_copy_implementations)]
+#[cfg_attr(docsrs, doc(cfg(feature = "pool")))]
+pub struct PoolConfig {
+    min_idle: u32,
+    max_size: u32,
+    idle_timeout: Duration,
+}
+
+impl PoolConfig {
+    /// Create a new pool configuration with default values
+    pub fn new() -> Self {
+        Self::default()
+    }
+
+    /// Minimum number of idle connections
+    ///
+    /// Defaults to `0`
+    pub fn min_idle(mut self, min_idle: u32) -> Self {
+        self.min_idle = min_idle;
+        self
+    }
+
+    /// Maximum number of pooled connections
+    ///
+    /// Defaults to `10`
+    pub fn max_size(mut self, max_size: u32) -> Self {
+        self.max_size = max_size;
+        self
+    }
+
+    /// Connection timeout
+    ///
+    /// Defaults to `30 seconds`
+    #[doc(hidden)]
+    #[deprecated(note = "The Connection timeout is already configured on the SMTP transport")]
+    pub fn connection_timeout(self, connection_timeout: Duration) -> Self {
+        let _ = connection_timeout;
+        self
+    }
+
+    /// Connection idle timeout
+    ///
+    /// Defaults to `60 seconds`
+    pub fn idle_timeout(mut self, idle_timeout: Duration) -> Self {
+        self.idle_timeout = idle_timeout;
+        self
+    }
+}
+
+impl Default for PoolConfig {
+    fn default() -> Self {
+        Self {
+            min_idle: 0,
+            max_size: 10,
+            idle_timeout: Duration::from_secs(60),
+        }
+    }
+}

src/transport/smtp/pool/sync_impl.rs

@@ -0,0 +1,308 @@
+use std::{
+    fmt::{self, Debug},
+    ops::{Deref, DerefMut},
+    sync::{mpsc, Arc, Mutex, TryLockError},
+    thread,
+    time::{Duration, Instant},
+};
+
+use super::{
+    super::{client::SmtpConnection, Error},
+    PoolConfig,
+};
+use crate::transport::smtp::{error, transport::SmtpClient};
+
+pub(crate) struct Pool {
+    config: PoolConfig,
+    connections: Mutex<Option<Vec<ParkedConnection>>>,
+    thread_terminator: mpsc::SyncSender<()>,
+    client: SmtpClient,
+}
+
+struct ParkedConnection {
+    conn: SmtpConnection,
+    since: Instant,
+}
+
+pub(crate) struct PooledConnection {
+    conn: Option<SmtpConnection>,
+    pool: Arc<Pool>,
+}
+
+impl Pool {
+    pub(crate) fn new(config: PoolConfig, client: SmtpClient) -> Arc<Self> {
+        let (thread_tx, thread_rx) = mpsc::sync_channel(1);
+
+        let pool = Arc::new(Self {
+            config,
+            connections: Mutex::new(Some(Vec::new())),
+            thread_terminator: thread_tx,
+            client,
+        });
+
+        {
+            let pool_ = Arc::clone(&pool);
+
+            let min_idle = pool_.config.min_idle;
+            let idle_timeout = pool_.config.idle_timeout;
+            let pool = Arc::downgrade(&pool_);
+
+            thread::Builder::new()
+                .name("lettre-connection-pool".into())
+                .spawn(move || {
+                    while let Some(pool) = pool.upgrade() {
+                        #[cfg(feature = "tracing")]
+                        tracing::trace!("running cleanup tasks");
+
+                        #[allow(clippy::needless_collect)]
+                        let (count, dropped) = {
+                            let mut connections = pool.connections.lock().unwrap();
+                            let Some(connections) = connections.as_mut() else {
+                                // The transport was shut down
+                                return;
+                            };
+
+                            let to_drop = connections
+                                .iter()
+                                .enumerate()
+                                .rev()
+                                .filter(|(_, conn)| conn.idle_duration() > idle_timeout)
+                                .map(|(i, _)| i)
+                                .collect::<Vec<_>>();
+                            let dropped = to_drop
+                                .into_iter()
+                                .map(|i| connections.remove(i))
+                                .collect::<Vec<_>>();
+
+                            (connections.len(), dropped)
+                        };
+
+                        #[cfg(feature = "tracing")]
+                        let mut created = 0;
+                        for _ in count..(min_idle as usize) {
+                            let conn = match pool.client.connection() {
+                                Ok(conn) => conn,
+                                Err(err) => {
+                                    #[cfg(feature = "tracing")]
+                                    tracing::warn!("couldn't create idle connection {}", err);
+                                    #[cfg(not(feature = "tracing"))]
+                                    let _ = err;
+
+                                    break;
+                                }
+                            };
+
+                            let mut connections = pool.connections.lock().unwrap();
+                            let Some(connections) = connections.as_mut() else {
+                                // The transport was shut down
+                                return;
+                            };
+
+                            connections.push(ParkedConnection::park(conn));
+
+                            #[cfg(feature = "tracing")]
+                            {
+                                created += 1;
+                            }
+                        }
+
+                        #[cfg(feature = "tracing")]
+                        if created > 0 {
+                            tracing::debug!("created {} idle connections", created);
+                        }
+
+                        if !dropped.is_empty() {
+                            #[cfg(feature = "tracing")]
+                            tracing::debug!("dropped {} idle connections", dropped.len());
+
+                            for conn in dropped {
+                                let mut conn = conn.unpark();
+                                conn.abort();
+                            }
+                        }
+
+                        drop(pool);
+
+                        match thread_rx.recv_timeout(idle_timeout) {
+                            Ok(()) | Err(mpsc::RecvTimeoutError::Disconnected) => {
+                                // The transport was shut down
+                                return;
+                            }
+                            Err(mpsc::RecvTimeoutError::Timeout) => {}
+                        }
+                    }
+                })
+                .expect("couldn't spawn the Pool thread");
+        }
+
+        pool
+    }
+
+    pub(crate) fn shutdown(&self) {
+        let connections = { self.connections.lock().unwrap().take() };
+        if let Some(connections) = connections {
+            for conn in connections {
+                conn.unpark().abort();
+            }
+        }
+
+        _ = self.thread_terminator.try_send(());
+    }
+
+    pub(crate) fn connection(self: &Arc<Self>) -> Result<PooledConnection, Error> {
+        loop {
+            let conn = {
+                let mut connections = self.connections.lock().unwrap();
+                let Some(connections) = connections.as_mut() else {
+                    // The transport was shut down
+                    return Err(error::transport_shutdown());
+                };
+                connections.pop()
+            };
+
+            match conn {
+                Some(conn) => {
+                    let mut conn = conn.unpark();
+
+                    // TODO: handle the client try another connection if this one isn't good
+                    if !conn.test_connected() {
+                        #[cfg(feature = "tracing")]
+                        tracing::debug!("dropping a broken connection");
+
+                        conn.abort();
+                        continue;
+                    }
+
+                    #[cfg(feature = "tracing")]
+                    tracing::debug!("reusing a pooled connection");
+
+                    return Ok(PooledConnection::wrap(conn, Arc::clone(self)));
+                }
+                None => {
+                    #[cfg(feature = "tracing")]
+                    tracing::debug!("creating a new connection");
+
+                    let conn = self.client.connection()?;
+                    return Ok(PooledConnection::wrap(conn, Arc::clone(self)));
+                }
+            }
+        }
+    }
+
+    fn recycle(&self, mut conn: SmtpConnection) {
+        if conn.has_broken() {
+            #[cfg(feature = "tracing")]
+            tracing::debug!("dropping a broken connection instead of recycling it");
+
+            conn.abort();
+            drop(conn);
+        } else {
+            #[cfg(feature = "tracing")]
+            tracing::debug!("recycling connection");
+
+            let mut connections_guard = self.connections.lock().unwrap();
+
+            if let Some(connections) = connections_guard.as_mut() {
+                if connections.len() >= self.config.max_size as usize {
+                    drop(connections_guard);
+                    conn.abort();
+                } else {
+                    let conn = ParkedConnection::park(conn);
+                    connections.push(conn);
+                }
+            } else {
+                // The pool has already been shut down
+                drop(connections_guard);
+                conn.abort();
+            }
+        }
+    }
+}
+
+impl Debug for Pool {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        f.debug_struct("Pool")
+            .field("config", &self.config)
+            .field(
+                "connections",
+                &match self.connections.try_lock() {
+                    Ok(connections) => {
+                        if let Some(connections) = connections.as_ref() {
+                            format!("{} connections", connections.len())
+                        } else {
+                            "SHUT DOWN".to_owned()
+                        }
+                    }
+
+                    Err(TryLockError::WouldBlock) => "LOCKED".to_owned(),
+                    Err(TryLockError::Poisoned(_)) => "POISONED".to_owned(),
+                },
+            )
+            .field("client", &self.client)
+            .finish()
+    }
+}
+
+impl Drop for Pool {
+    fn drop(&mut self) {
+        #[cfg(feature = "tracing")]
+        tracing::debug!("dropping Pool");
+
+        if let Some(connections) = self.connections.get_mut().unwrap().take() {
+            for conn in connections {
+                let mut conn = conn.unpark();
+                conn.abort();
+            }
+        }
+    }
+}
+
+impl ParkedConnection {
+    fn park(conn: SmtpConnection) -> Self {
+        Self {
+            conn,
+            since: Instant::now(),
+        }
+    }
+
+    fn idle_duration(&self) -> Duration {
+        self.since.elapsed()
+    }
+
+    fn unpark(self) -> SmtpConnection {
+        self.conn
+    }
+}
+
+impl PooledConnection {
+    fn wrap(conn: SmtpConnection, pool: Arc<Pool>) -> Self {
+        Self {
+            conn: Some(conn),
+            pool,
+        }
+    }
+}
+
+impl Deref for PooledConnection {
+    type Target = SmtpConnection;
+
+    fn deref(&self) -> &Self::Target {
+        self.conn.as_ref().expect("conn hasn't been dropped yet")
+    }
+}
+
+impl DerefMut for PooledConnection {
+    fn deref_mut(&mut self) -> &mut Self::Target {
+        self.conn.as_mut().expect("conn hasn't been dropped yet")
+    }
+}
+
+impl Drop for PooledConnection {
+    fn drop(&mut self) {
+        let conn = self
+            .conn
+            .take()
+            .expect("SmtpConnection hasn't been taken yet");
+        self.pool.recycle(conn);
+    }
+}

src/transport/smtp/response.rs

@@ -1,23 +1,24 @@
 //! SMTP response, containing a mandatory return code and an optional text
 //! message
 
-use crate::transport::smtp::Error;
+use std::{
+    fmt::{Display, Formatter, Result},
+    result,
+    str::FromStr,
+};
+
 use nom::{
     branch::alt,
     bytes::streaming::{tag, take_until},
     combinator::{complete, map},
     multi::many0,
-    sequence::{preceded, tuple},
-    IResult,
-};
-use std::{
-    fmt::{Display, Formatter, Result},
-    result,
-    str::FromStr,
-    string::ToString,
+    sequence::preceded,
+    IResult, Parser,
 };
 
-/// First digit indicates severity
+use crate::transport::smtp::{error, Error};
+
+/// The first digit indicates severity
 #[derive(PartialEq, Eq, Copy, Clone, Debug)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 pub enum Severity {
@@ -120,6 +121,20 @@ impl Code {
             detail,
         }
     }
+
+    /// Tells if the response is positive
+    pub fn is_positive(self) -> bool {
+        matches!(
+            self.severity,
+            Severity::PositiveCompletion | Severity::PositiveIntermediate
+        )
+    }
+}
+
+impl From<Code> for u16 {
+    fn from(code: Code) -> Self {
+        code.detail as u16 + 10 * code.category as u16 + 100 * code.severity as u16
+    }
 }
 
 /// Contains an SMTP reply, with separated code and message
@@ -129,17 +144,19 @@ impl Code {
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 pub struct Response {
     /// Response code
-    pub code: Code,
+    code: Code,
     /// Server response string (optional)
     /// Handle multiline responses
-    pub message: Vec<String>,
+    message: Vec<String>,
 }
 
 impl FromStr for Response {
     type Err = Error;
 
     fn from_str(s: &str) -> result::Result<Response, Error> {
-        parse_response(s).map(|(_, r)| r).map_err(|e| e.into())
+        parse_response(s)
+            .map(|(_, r)| r)
+            .map_err(|e| error::response(e.to_owned()))
     }
 }
 
@@ -151,10 +168,7 @@ impl Response {
 
     /// Tells if the response is positive
     pub fn is_positive(&self) -> bool {
-        matches!(
-            self.code.severity,
-            Severity::PositiveCompletion | Severity::PositiveIntermediate
-        )
+        self.code.is_positive()
     }
 
     /// Tests code equality
@@ -173,6 +187,16 @@ impl Response {
     pub fn first_line(&self) -> Option<&str> {
         self.message.first().map(String::as_str)
     }
+
+    /// Response code
+    pub fn code(&self) -> Code {
+        self.code
+    }
+
+    /// Server response string (array of lines)
+    pub fn message(&self) -> impl Iterator<Item = &str> {
+        self.message.iter().map(String::as_str)
+    }
 }
 
 // Parsers (originally from tokio-smtp)
@@ -197,7 +221,8 @@ fn parse_severity(i: &str) -> IResult<&str, Severity> {
         map(tag("3"), |_| Severity::PositiveIntermediate),
         map(tag("4"), |_| Severity::TransientNegativeCompletion),
         map(tag("5"), |_| Severity::PermanentNegativeCompletion),
-    ))(i)
+    ))
+    .parse(i)
 }
 
 fn parse_category(i: &str) -> IResult<&str, Category> {
@@ -208,7 +233,8 @@ fn parse_category(i: &str) -> IResult<&str, Category> {
         map(tag("3"), |_| Category::Unspecified3),
         map(tag("4"), |_| Category::Unspecified4),
         map(tag("5"), |_| Category::MailSystem),
-    ))(i)
+    ))
+    .parse(i)
 }
 
 fn parse_detail(i: &str) -> IResult<&str, Detail> {
@@ -223,18 +249,20 @@ fn parse_detail(i: &str) -> IResult<&str, Detail> {
         map(tag("7"), |_| Detail::Seven),
         map(tag("8"), |_| Detail::Eight),
         map(tag("9"), |_| Detail::Nine),
-    ))(i)
+    ))
+    .parse(i)
 }
 
 pub(crate) fn parse_response(i: &str) -> IResult<&str, Response> {
-    let (i, lines) = many0(tuple((
+    let (i, lines) = many0((
         parse_code,
         preceded(tag("-"), take_until("\r\n")),
         tag("\r\n"),
-    )))(i)?;
+    ))
+    .parse(i)?;
     let (i, (last_code, last_line)) =
-        tuple((parse_code, preceded(tag(" "), take_until("\r\n"))))(i)?;
-    let (i, _) = complete(tag("\r\n"))(i)?;
+        (parse_code, preceded(tag(" "), take_until("\r\n"))).parse(i)?;
+    let (i, _) = complete(tag("\r\n")).parse(i)?;
 
     // Check that all codes are equal.
     if !lines.iter().all(|&(code, _, _)| code == last_code) {
@@ -298,6 +326,17 @@ mod test {
         assert_eq!(code.to_string(), "421");
     }
 
+    #[test]
+    fn test_code_to_u16() {
+        let code = Code {
+            severity: Severity::TransientNegativeCompletion,
+            category: Category::Connections,
+            detail: Detail::One,
+        };
+        let c: u16 = code.into();
+        assert_eq!(c, 421);
+    }
+
     #[test]
     fn test_response_from_str() {
         let raw_response = "250-me\r\n250-8BITMIME\r\n250-SIZE 42\r\n250 AUTH PLAIN CRAM-MD5\r\n";
@@ -310,10 +349,10 @@ mod test {
                     detail: Detail::Zero,
                 },
                 message: vec![
-                    "me".to_string(),
-                    "8BITMIME".to_string(),
-                    "SIZE 42".to_string(),
-                    "AUTH PLAIN CRAM-MD5".to_string(),
+                    "me".to_owned(),
+                    "8BITMIME".to_owned(),
+                    "SIZE 42".to_owned(),
+                    "AUTH PLAIN CRAM-MD5".to_owned(),
                 ],
             }
         );
@@ -333,11 +372,7 @@ mod test {
                 category: Category::MailSystem,
                 detail: Detail::Zero,
             },
-            vec![
-                "me".to_string(),
-                "8BITMIME".to_string(),
-                "SIZE 42".to_string(),
-            ],
+            vec!["me".to_owned(), "8BITMIME".to_owned(), "SIZE 42".to_owned(),],
         )
         .is_positive());
         assert!(!Response::new(
@@ -346,11 +381,7 @@ mod test {
                 category: Category::MailSystem,
                 detail: Detail::Zero,
             },
-            vec![
-                "me".to_string(),
-                "8BITMIME".to_string(),
-                "SIZE 42".to_string(),
-            ],
+            vec!["me".to_owned(), "8BITMIME".to_owned(), "SIZE 42".to_owned(),],
         )
         .is_positive());
     }
@@ -363,11 +394,7 @@ mod test {
                 category: Category::MailSystem,
                 detail: Detail::One,
             },
-            vec![
-                "me".to_string(),
-                "8BITMIME".to_string(),
-                "SIZE 42".to_string(),
-            ],
+            vec!["me".to_owned(), "8BITMIME".to_owned(), "SIZE 42".to_owned(),],
         )
         .has_code(451));
         assert!(!Response::new(
@@ -376,11 +403,7 @@ mod test {
                 category: Category::MailSystem,
                 detail: Detail::One,
             },
-            vec![
-                "me".to_string(),
-                "8BITMIME".to_string(),
-                "SIZE 42".to_string(),
-            ],
+            vec!["me".to_owned(), "8BITMIME".to_owned(), "SIZE 42".to_owned(),],
         )
         .has_code(251));
     }
@@ -394,11 +417,7 @@ mod test {
                     category: Category::MailSystem,
                     detail: Detail::One,
                 },
-                vec![
-                    "me".to_string(),
-                    "8BITMIME".to_string(),
-                    "SIZE 42".to_string(),
-                ],
+                vec!["me".to_owned(), "8BITMIME".to_owned(), "SIZE 42".to_owned(),],
             )
             .first_word(),
             Some("me")
@@ -411,9 +430,9 @@ mod test {
                     detail: Detail::One,
                 },
                 vec![
-                    "me mo".to_string(),
-                    "8BITMIME".to_string(),
-                    "SIZE 42".to_string(),
+                    "me mo".to_owned(),
+                    "8BITMIME".to_owned(),
+                    "SIZE 42".to_owned(),
                 ],
             )
             .first_word(),
@@ -438,7 +457,7 @@ mod test {
                     category: Category::MailSystem,
                     detail: Detail::One,
                 },
-                vec![" ".to_string()],
+                vec![" ".to_owned()],
             )
             .first_word(),
             None
@@ -450,7 +469,7 @@ mod test {
                     category: Category::MailSystem,
                     detail: Detail::One,
                 },
-                vec!["  ".to_string()],
+                vec!["  ".to_owned()],
             )
             .first_word(),
             None
@@ -462,7 +481,7 @@ mod test {
                     category: Category::MailSystem,
                     detail: Detail::One,
                 },
-                vec!["".to_string()],
+                vec!["".to_owned()],
             )
             .first_word(),
             None
@@ -475,7 +494,7 @@ mod test {
         let res = parse_response(raw_response);
         match res {
             Err(nom::Err::Incomplete(_)) => {}
-            _ => panic!("Expected incomplete response, got {:?}", res),
+            _ => panic!("Expected incomplete response, got {res:?}"),
         }
     }
 
@@ -488,11 +507,7 @@ mod test {
                     category: Category::MailSystem,
                     detail: Detail::One,
                 },
-                vec![
-                    "me".to_string(),
-                    "8BITMIME".to_string(),
-                    "SIZE 42".to_string(),
-                ],
+                vec!["me".to_owned(), "8BITMIME".to_owned(), "SIZE 42".to_owned(),],
             )
             .first_line(),
             Some("me")
@@ -505,9 +520,9 @@ mod test {
                     detail: Detail::One,
                 },
                 vec![
-                    "me mo".to_string(),
-                    "8BITMIME".to_string(),
-                    "SIZE 42".to_string(),
+                    "me mo".to_owned(),
+                    "8BITMIME".to_owned(),
+                    "SIZE 42".to_owned(),
                 ],
             )
             .first_line(),
@@ -532,7 +547,7 @@ mod test {
                     category: Category::MailSystem,
                     detail: Detail::One,
                 },
-                vec![" ".to_string()],
+                vec![" ".to_owned()],
             )
             .first_line(),
             Some(" ")
@@ -544,7 +559,7 @@ mod test {
                     category: Category::MailSystem,
                     detail: Detail::One,
                 },
-                vec!["  ".to_string()],
+                vec!["  ".to_owned()],
             )
             .first_line(),
             Some("  ")
@@ -556,7 +571,7 @@ mod test {
                     category: Category::MailSystem,
                     detail: Detail::One,
                 },
-                vec!["".to_string()],
+                vec!["".to_owned()],
             )
             .first_line(),
             Some("")

src/transport/smtp/transport.rs

@@ -1,22 +1,47 @@
-use std::time::Duration;
+#[cfg(feature = "pool")]
+use std::sync::Arc;
+use std::{fmt::Debug, time::Duration};
 
-#[cfg(feature = "r2d2")]
-use r2d2::Pool;
-
-#[cfg(feature = "r2d2")]
+#[cfg(feature = "pool")]
+use super::pool::sync_impl::Pool;
+#[cfg(feature = "pool")]
 use super::PoolConfig;
 use super::{ClientId, Credentials, Error, Mechanism, Response, SmtpConnection, SmtpInfo};
-#[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
+#[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
 use super::{Tls, TlsParameters, SUBMISSIONS_PORT, SUBMISSION_PORT};
-use crate::address::Envelope;
-use crate::Transport;
+use crate::{address::Envelope, Transport};
 
-#[allow(missing_debug_implementations)]
+/// Synchronously send emails using the SMTP protocol
+///
+/// `SmtpTransport` is the primary way for communicating
+/// with SMTP relay servers to send email messages. It holds the
+/// client connect configuration and creates new connections
+/// as necessary.
+///
+/// # Connection pool
+///
+/// When the `pool` feature is enabled (default), `SmtpTransport` maintains a
+/// connection pool to manage SMTP connections. The pool:
+///
+/// - Establishes a new connection when sending a message.
+/// - Recycles connections internally after a message is sent.
+/// - Reuses connections for subsequent messages, reducing connection setup overhead.
+///
+/// The connection pool can grow to hold multiple SMTP connections if multiple
+/// emails are sent concurrently, as SMTP does not support multiplexing within a
+/// single connection.
+///
+/// However, **connection reuse is not possible** if the `SmtpTransport` instance
+/// is dropped after every email send operation. You must reuse the instance
+/// of this struct for the connection pool to be of any use.
+///
+/// To customize connection pool settings, use [`SmtpTransportBuilder::pool_config`].
+#[cfg_attr(docsrs, doc(cfg(feature = "smtp-transport")))]
 #[derive(Clone)]
 pub struct SmtpTransport {
-    #[cfg(feature = "r2d2")]
-    inner: Pool<SmtpClient>,
-    #[cfg(not(feature = "r2d2"))]
+    #[cfg(feature = "pool")]
+    inner: Arc<Pool>,
+    #[cfg(not(feature = "pool"))]
     inner: SmtpClient,
 }
 
@@ -26,18 +51,28 @@ impl Transport for SmtpTransport {
 
     /// Sends an email
     fn send_raw(&self, envelope: &Envelope, email: &[u8]) -> Result<Self::Ok, Self::Error> {
-        #[cfg(feature = "r2d2")]
-        let mut conn = self.inner.get()?;
-        #[cfg(not(feature = "r2d2"))]
         let mut conn = self.inner.connection()?;
 
         let result = conn.send(envelope, email)?;
 
-        #[cfg(not(feature = "r2d2"))]
-        conn.quit()?;
+        #[cfg(not(feature = "pool"))]
+        conn.abort();
 
         Ok(result)
     }
+
+    fn shutdown(&self) {
+        #[cfg(feature = "pool")]
+        self.inner.shutdown();
+    }
+}
+
+impl Debug for SmtpTransport {
+    fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
+        let mut builder = f.debug_struct("SmtpTransport");
+        builder.field("inner", &self.inner);
+        builder.finish()
+    }
 }
 
 impl SmtpTransport {
@@ -47,7 +82,11 @@ impl SmtpTransport {
     ///
     /// Creates an encrypted transport over submissions port, using the provided domain
     /// to validate TLS certificates.
-    #[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
+    #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+    #[cfg_attr(
+        docsrs,
+        doc(cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls")))
+    )]
     pub fn relay(relay: &str) -> Result<SmtpTransportBuilder, Error> {
         let tls_parameters = TlsParameters::new(relay.into())?;
 
@@ -56,7 +95,7 @@ impl SmtpTransport {
             .tls(Tls::Wrapper(tls_parameters)))
     }
 
-    /// Simple an secure transport, using STARTTLS to obtain encrypted connections
+    /// Simple and secure transport, using STARTTLS to obtain encrypted connections
     ///
     /// Alternative to [`SmtpTransport::relay`](#method.relay), for SMTP servers
     /// that don't take SMTPS connections.
@@ -67,7 +106,11 @@ impl SmtpTransport {
     ///
     /// An error is returned if the connection can't be upgraded. No credentials
     /// or emails will be sent to the server, protecting from downgrade attacks.
-    #[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
+    #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+    #[cfg_attr(
+        docsrs,
+        doc(cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls")))
+    )]
     pub fn starttls_relay(relay: &str) -> Result<SmtpTransportBuilder, Error> {
         let tls_parameters = TlsParameters::new(relay.into())?;
 
@@ -89,45 +132,166 @@ impl SmtpTransport {
     ///
     /// * No authentication
     /// * No TLS
-    /// * A 60 seconds timeout for smtp commands
+    /// * A 60-seconds timeout for smtp commands
     /// * Port 25
     ///
     /// Consider using [`SmtpTransport::relay`](#method.relay) or
     /// [`SmtpTransport::starttls_relay`](#method.starttls_relay) instead,
     /// if possible.
     pub fn builder_dangerous<T: Into<String>>(server: T) -> SmtpTransportBuilder {
-        let new = SmtpInfo {
-            server: server.into(),
-            ..Default::default()
-        };
+        SmtpTransportBuilder::new(server)
+    }
 
-        SmtpTransportBuilder {
-            info: new,
-            #[cfg(feature = "r2d2")]
-            pool_config: PoolConfig::default(),
-        }
+    /// Creates a `SmtpTransportBuilder` from a connection URL
+    ///
+    /// The protocol, credentials, host, port and EHLO name can be provided
+    /// in a single URL. This may be simpler than having to configure SMTP
+    /// through multiple configuration parameters and then having to pass
+    /// those options to lettre.
+    ///
+    /// The URL is created in the following way:
+    /// `scheme://user:pass@hostname:port/ehlo-name?tls=TLS`.
+    ///
+    /// `user` (Username) and `pass` (Password) are optional in case the
+    /// SMTP relay doesn't require authentication. When `port` is not
+    /// configured it is automatically determined based on the `scheme`.
+    /// `ehlo-name` optionally overwrites the hostname sent for the EHLO
+    /// command. `TLS` controls whether STARTTLS is simply enabled
+    /// (`opportunistic` - not enough to prevent man-in-the-middle attacks)
+    /// or `required` (require the server to upgrade the connection to
+    /// STARTTLS, otherwise fail on suspicion of main-in-the-middle attempt).
+    ///
+    /// Use the following table to construct your SMTP url:
+    ///
+    /// | scheme  | `tls` query parameter | example                                            | default port | remarks                                                                                                                               |
+    /// | ------- | --------------------- | -------------------------------------------------- | ------------ | ------------------------------------------------------------------------------------------------------------------------------------- |
+    /// | `smtps` | unset                 | `smtps://user:pass@hostname:port`                  | 465          | SMTP over TLS, recommended method                                                                                                     |
+    /// | `smtp`  | `required`            | `smtp://user:pass@hostname:port?tls=required`      | 587          | SMTP with STARTTLS required, when SMTP over TLS is not available                                                                      |
+    /// | `smtp`  | `opportunistic`       | `smtp://user:pass@hostname:port?tls=opportunistic` | 587          | SMTP with optionally STARTTLS when supported by the server. Not suitable for production use: vulnerable to a man-in-the-middle attack |
+    /// | `smtp`  | unset                 | `smtp://user:pass@hostname:port`                   | 587          | Always unencrypted SMTP. Not suitable for production use: sends all data unencrypted                                                  |
+    ///
+    /// IMPORTANT: some parameters like `user` and `pass` cannot simply
+    /// be concatenated to construct the final URL because special characters
+    /// contained within the parameter may confuse the URL decoder.
+    /// Manually URL encode the parameters before concatenating them or use
+    /// a proper URL encoder, like the following cargo script:
+    ///
+    /// ```rust
+    /// # let _ = r#"
+    /// #!/usr/bin/env cargo
+    ///
+    /// //! ```cargo
+    /// //! [dependencies]
+    /// //! url = "2"
+    /// //! ```
+    /// # "#;
+    ///
+    /// use url::Url;
+    ///
+    /// fn main() {
+    ///     // don't touch this line
+    ///     let mut url = Url::parse("foo://bar").unwrap();
+    ///
+    ///     // configure the scheme (`smtp` or `smtps`) here.
+    ///     url.set_scheme("smtps").unwrap();
+    ///     // configure the username and password.
+    ///     // remove the following two lines if unauthenticated.
+    ///     url.set_username("username").unwrap();
+    ///     url.set_password(Some("password")).unwrap();
+    ///     // configure the hostname
+    ///     url.set_host(Some("smtp.example.com")).unwrap();
+    ///     // configure the port - only necessary if using a non-default port
+    ///     url.set_port(Some(465)).unwrap();
+    ///     // configure the EHLO name
+    ///     url.set_path("ehlo-name");
+    ///
+    ///     println!("{url}");
+    /// }
+    /// ```
+    ///
+    /// The connection URL can then be used in the following way:
+    ///
+    /// ```rust,no_run
+    /// use lettre::{
+    ///     message::header::ContentType, transport::smtp::authentication::Credentials, Message,
+    ///     SmtpTransport, Transport,
+    /// };
+    ///
+    /// # fn main() -> Result<(), Box<dyn std::error::Error>> {
+    /// let email = Message::builder()
+    ///     .from("NoBody <nobody@domain.tld>".parse().unwrap())
+    ///     .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
+    ///     .to("Hei <hei@domain.tld>".parse().unwrap())
+    ///     .subject("Happy new year")
+    ///     .header(ContentType::TEXT_PLAIN)
+    ///     .body(String::from("Be happy!"))
+    ///     .unwrap();
+    ///
+    /// // Open a remote connection to example
+    /// let mailer = SmtpTransport::from_url("smtps://username:password@smtp.example.com")?.build();
+    ///
+    /// // Send the email
+    /// mailer.send(&email)?;
+    /// # Ok(())
+    /// # }
+    /// ```
+    #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+    #[cfg_attr(
+        docsrs,
+        doc(cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls")))
+    )]
+    pub fn from_url(connection_url: &str) -> Result<SmtpTransportBuilder, Error> {
+        super::connection_url::from_connection_url(connection_url)
+    }
+
+    /// Tests the SMTP connection
+    ///
+    /// `test_connection()` tests the connection by using the SMTP NOOP command.
+    /// The connection is closed afterward if a connection pool is not used.
+    pub fn test_connection(&self) -> Result<bool, Error> {
+        let mut conn = self.inner.connection()?;
+
+        let is_connected = conn.test_connected();
+
+        #[cfg(not(feature = "pool"))]
+        conn.quit()?;
+
+        Ok(is_connected)
     }
 }
 
 /// Contains client configuration.
 /// Instances of this struct can be created using functions of [`SmtpTransport`].
-#[allow(missing_debug_implementations)]
-#[derive(Clone)]
+#[derive(Debug, Clone)]
 pub struct SmtpTransportBuilder {
     info: SmtpInfo,
-    #[cfg(feature = "r2d2")]
+    #[cfg(feature = "pool")]
     pool_config: PoolConfig,
 }
 
 /// Builder for the SMTP `SmtpTransport`
 impl SmtpTransportBuilder {
+    // Create new builder with default parameters
+    pub(crate) fn new<T: Into<String>>(server: T) -> Self {
+        let new = SmtpInfo {
+            server: server.into(),
+            ..Default::default()
+        };
+
+        Self {
+            info: new,
+            #[cfg(feature = "pool")]
+            pool_config: PoolConfig::default(),
+        }
+    }
+
     /// Set the name used during EHLO
     pub fn hello_name(mut self, name: ClientId) -> Self {
         self.info.hello_name = name;
         self
     }
 
-    /// Set the authentication mechanism to use
+    /// Set the authentication credentials to use
     pub fn credentials(mut self, credentials: Credentials) -> Self {
         self.info.credentials = Some(credentials);
         self
@@ -146,13 +310,39 @@ impl SmtpTransportBuilder {
     }
 
     /// Set the port to use
+    ///
+    /// # ⚠️⚠️⚠️ You probably don't need to call this method ⚠️⚠️⚠️
+    ///
+    /// lettre usually picks the correct `port` when building
+    /// [`SmtpTransport`] using [`SmtpTransport::relay`] or
+    /// [`SmtpTransport::starttls_relay`].
+    ///
+    /// # Errors
+    ///
+    /// Using the incorrect `port` and [`Self::tls`] combination may
+    /// lead to hard to debug IO errors coming from the TLS library.
     pub fn port(mut self, port: u16) -> Self {
         self.info.port = port;
         self
     }
 
     /// Set the TLS settings to use
-    #[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
+    ///
+    /// # ⚠️⚠️⚠️ You probably don't need to call this method ⚠️⚠️⚠️
+    ///
+    /// By default lettre chooses the correct `tls` configuration when
+    /// building [`SmtpTransport`] using [`SmtpTransport::relay`] or
+    /// [`SmtpTransport::starttls_relay`].
+    ///
+    /// # Errors
+    ///
+    /// Using the wrong [`Tls`] and [`Self::port`] combination may
+    /// lead to hard to debug IO errors coming from the TLS library.
+    #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+    #[cfg_attr(
+        docsrs,
+        doc(cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls")))
+    )]
     pub fn tls(mut self, tls: Tls) -> Self {
         self.info.tls = tls;
         self
@@ -161,8 +351,8 @@ impl SmtpTransportBuilder {
     /// Use a custom configuration for the connection pool
     ///
     /// Defaults can be found at [`PoolConfig`]
-    #[cfg(feature = "r2d2")]
-    #[cfg_attr(docsrs, doc(cfg(feature = "r2d2")))]
+    #[cfg(feature = "pool")]
+    #[cfg_attr(docsrs, doc(cfg(feature = "pool")))]
     pub fn pool_config(mut self, pool_config: PoolConfig) -> Self {
         self.pool_config = pool_config;
         self
@@ -170,22 +360,21 @@ impl SmtpTransportBuilder {
 
     /// Build the transport
     ///
-    /// If the `r2d2` feature is enabled an `Arc` wrapped pool is be created.
+    /// If the `pool` feature is enabled, an `Arc` wrapped pool is created.
     /// Defaults can be found at [`PoolConfig`]
     pub fn build(self) -> SmtpTransport {
         let client = SmtpClient { info: self.info };
-        SmtpTransport {
-            #[cfg(feature = "r2d2")]
-            inner: self.pool_config.build(client),
-            #[cfg(not(feature = "r2d2"))]
-            inner: client,
-        }
+
+        #[cfg(feature = "pool")]
+        let client = Pool::new(self.pool_config, client);
+
+        SmtpTransport { inner: client }
     }
 }
 
 /// Build client
-#[derive(Clone)]
-pub struct SmtpClient {
+#[derive(Debug, Clone)]
+pub(super) struct SmtpClient {
     info: SmtpInfo,
 }
 
@@ -193,11 +382,11 @@ impl SmtpClient {
     /// Creates a new connection directly usable to send emails
     ///
     /// Handles encryption and authentication
-    pub fn connection(&self) -> Result<SmtpConnection, Error> {
+    pub(super) fn connection(&self) -> Result<SmtpConnection, Error> {
         #[allow(clippy::match_single_binding)]
-        let tls_parameters = match self.info.tls {
-            #[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
-            Tls::Wrapper(ref tls_parameters) => Some(tls_parameters),
+        let tls_parameters = match &self.info.tls {
+            #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+            Tls::Wrapper(tls_parameters) => Some(tls_parameters),
             _ => None,
         };
 
@@ -207,24 +396,100 @@ impl SmtpClient {
             self.info.timeout,
             &self.info.hello_name,
             tls_parameters,
+            None,
         )?;
 
-        #[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
-        match self.info.tls {
-            Tls::Opportunistic(ref tls_parameters) => {
+        #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+        match &self.info.tls {
+            Tls::Opportunistic(tls_parameters) => {
                 if conn.can_starttls() {
                     conn.starttls(tls_parameters, &self.info.hello_name)?;
                 }
             }
-            Tls::Required(ref tls_parameters) => {
+            Tls::Required(tls_parameters) => {
                 conn.starttls(tls_parameters, &self.info.hello_name)?;
             }
             _ => (),
         }
 
         if let Some(credentials) = &self.info.credentials {
-            conn.auth(&self.info.authentication, &credentials)?;
+            conn.auth(&self.info.authentication, credentials)?;
         }
         Ok(conn)
     }
 }
+
+#[cfg(test)]
+mod tests {
+    use crate::{
+        transport::smtp::{authentication::Credentials, client::Tls},
+        SmtpTransport,
+    };
+
+    #[test]
+    fn transport_from_url() {
+        let builder = SmtpTransport::from_url("smtp://127.0.0.1:2525").unwrap();
+
+        assert_eq!(builder.info.port, 2525);
+        assert!(matches!(builder.info.tls, Tls::None));
+        assert_eq!(builder.info.server, "127.0.0.1");
+
+        let builder =
+            SmtpTransport::from_url("smtps://username:password@smtp.example.com:465").unwrap();
+
+        assert_eq!(builder.info.port, 465);
+        assert_eq!(
+            builder.info.credentials,
+            Some(Credentials::new(
+                "username".to_owned(),
+                "password".to_owned()
+            ))
+        );
+        assert!(matches!(builder.info.tls, Tls::Wrapper(_)));
+        assert_eq!(builder.info.server, "smtp.example.com");
+
+        let builder = SmtpTransport::from_url(
+            "smtps://user%40example.com:pa$$word%3F%22!@smtp.example.com:465",
+        )
+        .unwrap();
+
+        assert_eq!(builder.info.port, 465);
+        assert_eq!(
+            builder.info.credentials,
+            Some(Credentials::new(
+                "user@example.com".to_owned(),
+                "pa$$word?\"!".to_owned()
+            ))
+        );
+        assert!(matches!(builder.info.tls, Tls::Wrapper(_)));
+        assert_eq!(builder.info.server, "smtp.example.com");
+
+        let builder =
+            SmtpTransport::from_url("smtp://username:password@smtp.example.com:587?tls=required")
+                .unwrap();
+
+        assert_eq!(builder.info.port, 587);
+        assert_eq!(
+            builder.info.credentials,
+            Some(Credentials::new(
+                "username".to_owned(),
+                "password".to_owned()
+            ))
+        );
+        assert!(matches!(builder.info.tls, Tls::Required(_)));
+
+        let builder = SmtpTransport::from_url(
+            "smtp://username:password@smtp.example.com:587?tls=opportunistic",
+        )
+        .unwrap();
+
+        assert_eq!(builder.info.port, 587);
+        assert!(matches!(builder.info.tls, Tls::Opportunistic(_)));
+
+        let builder = SmtpTransport::from_url("smtps://smtp.example.com").unwrap();
+
+        assert_eq!(builder.info.port, 465);
+        assert_eq!(builder.info.credentials, None);
+        assert!(matches!(builder.info.tls, Tls::Wrapper(_)));
+    }
+}

src/transport/smtp/util.rs

@@ -4,10 +4,9 @@ use std::fmt::{Display, Formatter, Result as FmtResult};
 
 /// Encode a string as xtext
 #[derive(Debug)]
-#[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
-pub struct XText<'a>(pub &'a str);
+pub(crate) struct XText<'a>(pub(crate) &'a str);
 
-impl<'a> Display for XText<'a> {
+impl Display for XText<'_> {
     fn fmt(&self, f: &mut Formatter<'_>) -> FmtResult {
         let mut rest = self.0;
         while let Some(idx) = rest.find(|c| c < '!' || c == '+' || c == '=') {
@@ -39,10 +38,8 @@ mod tests {
             ("bjørn", "bjørn"),
             ("Ø+= ❤️‰", "Ø+2B+3D+20❤️‰"),
             ("+", "+2B"),
-        ]
-        .iter()
-        {
-            assert_eq!(format!("{}", XText(input)), expect.to_string());
+        ] {
+            assert_eq!(format!("{}", XText(input)), (*expect).to_owned());
         }
     }
 }

src/transport/stub/mod.rs

@@ -1,44 +1,62 @@
-//! The stub transport only logs message envelope and drops the content. It can be useful for
-//! testing purposes.
+//! The stub transport logs message envelopes as well as contents. It can be useful for testing
+//! purposes.
 //!
-//! #### Stub Transport
+//! # Stub Transport
 //!
-//! The stub transport returns provided result and drops the content. It can be useful for
-//! testing purposes.
+//! The stub transport logs message envelopes as well as contents. It can be useful for testing
+//! purposes.
+//!
+//! # Examples
 //!
 //! ```rust
 //! # #[cfg(feature = "builder")]
 //! # {
-//! use lettre::{Message, Transport};
-//! use lettre::transport::stub::StubTransport;
+//! use lettre::{
+//!     message::header::ContentType, transport::stub::StubTransport, Message, Transport,
+//! };
 //!
 //! # use std::error::Error;
-//! # fn main() -> Result<(), Box<dyn Error>> {
+//! # fn try_main() -> Result<(), Box<dyn Error>> {
 //! let email = Message::builder()
 //!     .from("NoBody <nobody@domain.tld>".parse()?)
 //!     .reply_to("Yuin <yuin@domain.tld>".parse()?)
 //!     .to("Hei <hei@domain.tld>".parse()?)
 //!     .subject("Happy new year")
+//!     .header(ContentType::TEXT_PLAIN)
 //!     .body(String::from("Be happy!"))?;
 //!
 //! let mut sender = StubTransport::new_ok();
-//! let result = sender.send(&email);
-//! assert!(result.is_ok());
+//! sender.send(&email)?;
+//! assert_eq!(
+//!     sender.messages(),
+//!     vec![(
+//!         email.envelope().clone(),
+//!         String::from_utf8(email.formatted()).unwrap()
+//!     )],
+//! );
 //! # Ok(())
 //! # }
+//! # try_main().unwrap();
 //! # }
 //! ```
 
-use crate::address::Envelope;
-#[cfg(feature = "async-std1")]
-use crate::AsyncStd1Transport;
-#[cfg(feature = "tokio02")]
-use crate::Tokio02Transport;
-use crate::Transport;
-#[cfg(any(feature = "async-std1", feature = "tokio02"))]
-use async_trait::async_trait;
-use std::{error::Error as StdError, fmt};
+use std::{
+    error::Error as StdError,
+    fmt,
+    sync::{Arc, Mutex as StdMutex},
+};
 
+#[cfg(any(feature = "tokio1", feature = "async-std1"))]
+use async_trait::async_trait;
+#[cfg(any(feature = "tokio1", feature = "async-std1"))]
+use futures_util::lock::Mutex as FuturesMutex;
+
+#[cfg(any(feature = "tokio1", feature = "async-std1"))]
+use crate::AsyncTransport;
+use crate::{address::Envelope, Transport};
+
+/// An error returned by the stub transport
+#[non_exhaustive]
 #[derive(Debug, Copy, Clone)]
 pub struct Error;
 
@@ -50,58 +68,113 @@ impl fmt::Display for Error {
 
 impl StdError for Error {}
 
-/// This transport logs the message envelope and returns the given response
-#[derive(Debug, Clone, Copy)]
+/// This transport logs messages and always returns the given response
+#[derive(Debug, Clone)]
 pub struct StubTransport {
     response: Result<(), Error>,
+    message_log: Arc<StdMutex<Vec<(Envelope, String)>>>,
+}
+
+/// This transport logs messages and always returns the given response
+#[derive(Debug, Clone)]
+#[cfg(any(feature = "tokio1", feature = "async-std1"))]
+#[cfg_attr(docsrs, doc(cfg(any(feature = "tokio1", feature = "async-std1"))))]
+pub struct AsyncStubTransport {
+    response: Result<(), Error>,
+    message_log: Arc<FuturesMutex<Vec<(Envelope, String)>>>,
 }
 
 impl StubTransport {
     /// Creates a new transport that always returns the given Result
-    pub fn new(response: Result<(), Error>) -> StubTransport {
-        StubTransport { response }
+    pub fn new(response: Result<(), Error>) -> Self {
+        Self {
+            response,
+            message_log: Arc::new(StdMutex::new(vec![])),
+        }
     }
 
     /// Creates a new transport that always returns a success response
-    pub fn new_ok() -> StubTransport {
-        StubTransport { response: Ok(()) }
+    pub fn new_ok() -> Self {
+        Self {
+            response: Ok(()),
+            message_log: Arc::new(StdMutex::new(vec![])),
+        }
     }
 
     /// Creates a new transport that always returns an error
-    pub fn new_error() -> StubTransport {
-        StubTransport {
+    pub fn new_error() -> Self {
+        Self {
             response: Err(Error),
+            message_log: Arc::new(StdMutex::new(vec![])),
         }
     }
+
+    /// Return all logged messages sent using [`Transport::send_raw`]
+    pub fn messages(&self) -> Vec<(Envelope, String)> {
+        self.message_log
+            .lock()
+            .expect("Couldn't acquire lock to write message log")
+            .clone()
+    }
+}
+
+#[cfg(any(feature = "async-std1", feature = "tokio1"))]
+impl AsyncStubTransport {
+    /// Creates a new transport that always returns the given Result
+    pub fn new(response: Result<(), Error>) -> Self {
+        Self {
+            response,
+            message_log: Arc::new(FuturesMutex::new(vec![])),
+        }
+    }
+
+    /// Creates a new transport that always returns a success response
+    pub fn new_ok() -> Self {
+        Self {
+            response: Ok(()),
+            message_log: Arc::new(FuturesMutex::new(vec![])),
+        }
+    }
+
+    /// Creates a new transport that always returns an error
+    pub fn new_error() -> Self {
+        Self {
+            response: Err(Error),
+            message_log: Arc::new(FuturesMutex::new(vec![])),
+        }
+    }
+
+    /// Return all logged messages sent using [`AsyncTransport::send_raw`]
+    #[cfg(any(feature = "tokio1", feature = "async-std1"))]
+    pub async fn messages(&self) -> Vec<(Envelope, String)> {
+        self.message_log.lock().await.clone()
+    }
 }
 
 impl Transport for StubTransport {
     type Ok = ();
     type Error = Error;
 
-    fn send_raw(&self, _envelope: &Envelope, _email: &[u8]) -> Result<Self::Ok, Self::Error> {
+    fn send_raw(&self, envelope: &Envelope, email: &[u8]) -> Result<Self::Ok, Self::Error> {
+        self.message_log
+            .lock()
+            .expect("Couldn't acquire lock to write message log")
+            .push((envelope.clone(), String::from_utf8_lossy(email).into()));
         self.response
     }
 }
 
-#[cfg(feature = "async-std1")]
+#[cfg(any(feature = "tokio1", feature = "async-std1"))]
 #[async_trait]
-impl AsyncStd1Transport for StubTransport {
+impl AsyncTransport for AsyncStubTransport {
     type Ok = ();
     type Error = Error;
 
-    async fn send_raw(&self, _envelope: &Envelope, _email: &[u8]) -> Result<Self::Ok, Self::Error> {
-        self.response
-    }
-}
-
-#[cfg(feature = "tokio02")]
-#[async_trait]
-impl Tokio02Transport for StubTransport {
-    type Ok = ();
-    type Error = Error;
-
-    async fn send_raw(&self, _envelope: &Envelope, _email: &[u8]) -> Result<Self::Ok, Self::Error> {
+    async fn send_raw(&self, envelope: &Envelope, email: &[u8]) -> Result<Self::Ok, Self::Error> {
+        self.message_log
+            .lock()
+            .await
+            .push((envelope.clone(), String::from_utf8_lossy(email).into()));
         self.response
     }
 }

testdata/coredns.conf

@@ -0,0 +1,7 @@
+. {
+  bind 127.0.0.54
+  forward . 9.9.9.9 8.8.8.8 1.1.1.1 {
+    except example.org
+  }
+  file testdata/db.example.org example.org
+}

testdata/db.example.org

@@ -0,0 +1,2 @@
+@       600     IN      SOA     ns.example.org hostmaster.example.org 1 10800 3600 604800 3600
+dkimtest._domainkey 600 IN TXT  "v=DKIM1; k=rsa; p=MIIBIjANBgkqhkiG9w0BAQEFAAOCAQ8AMIIBCgKCAQEAz+FHbM8BwkBBz/Ux5OYLQ5Bp1HVuCHTP6Rr3HXTnome/2cGl/ze0tsmmFbCjjsS89MXbMGs9xJhjv18LmL1N0UTllblOizzVjorQyN4RwBOfG34j7SS56pwzrA738Ry8FAbL5InPWEgVzbOhXuTCs8yuzcqTnm4sH/csnIl7cMWeQkVn1FR9LKMtUG0fjhDPkdX0jx3qTX1L3Z7a7gX6geY191yNd9i9DvE2/+wMigMYz1LAts4alk2g86MQhtbjc8AOR7EC15hSw37/lmamlunYLa3wC+PzHNMA8sAfnmkgNvipssjh8LnelD9qn+VtsjQB5ppkeQx3TcUPvz5z+QIDAQAB"

testdata/email_with_png.eml

@@ -1,13 +1,14 @@
-Date: Tue, 15 Nov 1994 08:12:31 GMT
+Date: Tue, 15 Nov 1994 08:12:31 +0000
 From: NoBody <nobody@domain.tld>
 Reply-To: Yuin <yuin@domain.tld>
 To: Hei <hei@domain.tld>
 Subject: Happy new year
 MIME-Version: 1.0
-Content-Type: multipart/related; boundary="0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1"
+Content-Type: multipart/related;
+ boundary="GUEEoEeTXtLcK2sMhmH1RfC1co13g4rtnRUFjQFA"
 
 --0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1
-Content-Type: text/html; charset=utf8
+Content-Type: text/html; charset=utf-8
 Content-Transfer-Encoding: 7bit
 
 <p><b>Hello</b>, <i>world</i>! <img src=cid:123></p>

tests/transport_file.rs

@@ -1,32 +1,39 @@
+#[cfg(all(feature = "file-transport", feature = "builder"))]
+fn default_date() -> std::time::SystemTime {
+    use std::time::{Duration, SystemTime};
+
+    // Tue, 15 Nov 1994 08:12:31 GMT
+    SystemTime::UNIX_EPOCH + Duration::from_secs(784887151)
+}
+
 #[cfg(test)]
 #[cfg(all(feature = "file-transport", feature = "builder"))]
-mod test {
-    use lettre::{transport::file::FileTransport, Message};
+mod sync {
     use std::{
         env::temp_dir,
         fs::{read_to_string, remove_file},
     };
 
-    #[cfg(feature = "tokio02")]
-    use tokio02_crate as tokio;
+    use lettre::{FileTransport, Message, Transport};
+
+    use crate::default_date;
 
     #[test]
     fn file_transport() {
-        use lettre::Transport;
         let sender = FileTransport::new(temp_dir());
         let email = Message::builder()
             .from("NoBody <nobody@domain.tld>".parse().unwrap())
             .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
             .to("Hei <hei@domain.tld>".parse().unwrap())
             .subject("Happy new year")
-            .date("Tue, 15 Nov 1994 08:12:31 GMT".parse().unwrap())
+            .date(default_date())
             .body(String::from("Be happy!"))
             .unwrap();
 
         let result = sender.send(&email);
         let id = result.unwrap();
 
-        let eml_file = temp_dir().join(format!("{}.eml", id));
+        let eml_file = temp_dir().join(format!("{id}.eml"));
         let eml = read_to_string(&eml_file).unwrap();
 
         assert_eq!(
@@ -36,7 +43,7 @@ mod test {
                 "Reply-To: Yuin <yuin@domain.tld>\r\n",
                 "To: Hei <hei@domain.tld>\r\n",
                 "Subject: Happy new year\r\n",
-                "Date: Tue, 15 Nov 1994 08:12:31 GMT\r\n",
+                "Date: Tue, 15 Nov 1994 08:12:31 +0000\r\n",
                 "Content-Transfer-Encoding: 7bit\r\n",
                 "\r\n",
                 "Be happy!"
@@ -48,24 +55,23 @@ mod test {
     #[test]
     #[cfg(feature = "file-transport-envelope")]
     fn file_transport_with_envelope() {
-        use lettre::Transport;
         let sender = FileTransport::with_envelope(temp_dir());
         let email = Message::builder()
             .from("NoBody <nobody@domain.tld>".parse().unwrap())
             .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
             .to("Hei <hei@domain.tld>".parse().unwrap())
             .subject("Happy new year")
-            .date("Tue, 15 Nov 1994 08:12:31 GMT".parse().unwrap())
+            .date(default_date())
             .body(String::from("Be happy!"))
             .unwrap();
 
         let result = sender.send(&email);
         let id = result.unwrap();
 
-        let eml_file = temp_dir().join(format!("{}.eml", id));
+        let eml_file = temp_dir().join(format!("{id}.eml"));
         let eml = read_to_string(&eml_file).unwrap();
 
-        let json_file = temp_dir().join(format!("{}.json", id));
+        let json_file = temp_dir().join(format!("{id}.json"));
         let json = read_to_string(&json_file).unwrap();
 
         assert_eq!(
@@ -75,77 +81,57 @@ mod test {
                 "Reply-To: Yuin <yuin@domain.tld>\r\n",
                 "To: Hei <hei@domain.tld>\r\n",
                 "Subject: Happy new year\r\n",
-                "Date: Tue, 15 Nov 1994 08:12:31 GMT\r\n",
+                "Date: Tue, 15 Nov 1994 08:12:31 +0000\r\n",
                 "Content-Transfer-Encoding: 7bit\r\n",
                 "\r\n",
                 "Be happy!"
             )
         );
-        remove_file(eml_file).unwrap();
 
         assert_eq!(
             json,
             "{\"forward_path\":[\"hei@domain.tld\"],\"reverse_path\":\"nobody@domain.tld\"}"
         );
+
+        let (e, m) = sender.read(&id).unwrap();
+
+        assert_eq!(&e, email.envelope());
+        assert_eq!(m, email.formatted());
+
+        remove_file(eml_file).unwrap();
         remove_file(json_file).unwrap();
     }
+}
 
-    #[cfg(feature = "async-std1")]
-    #[async_std::test]
-    async fn file_transport_asyncstd1() {
-        use lettre::AsyncStd1Transport;
+#[cfg(test)]
+#[cfg(all(feature = "file-transport", feature = "builder", feature = "tokio1"))]
+mod tokio_1 {
+    use std::{
+        env::temp_dir,
+        fs::{read_to_string, remove_file},
+    };
 
-        let sender = FileTransport::new(temp_dir());
-        let email = Message::builder()
-            .from("NoBody <nobody@domain.tld>".parse().unwrap())
-            .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
-            .to("Hei <hei@domain.tld>".parse().unwrap())
-            .subject("Happy new year")
-            .date("Tue, 15 Nov 1994 08:12:31 GMT".parse().unwrap())
-            .body(String::from("Be happy!"))
-            .unwrap();
+    use lettre::{AsyncFileTransport, AsyncTransport, Message, Tokio1Executor};
+    use tokio1_crate as tokio;
 
-        let result = sender.send(email).await;
-        let id = result.unwrap();
+    use crate::default_date;
 
-        let eml_file = temp_dir().join(format!("{}.eml", id));
-        let eml = read_to_string(&eml_file).unwrap();
-
-        assert_eq!(
-            eml,
-            concat!(
-                "From: NoBody <nobody@domain.tld>\r\n",
-                "Reply-To: Yuin <yuin@domain.tld>\r\n",
-                "To: Hei <hei@domain.tld>\r\n",
-                "Subject: Happy new year\r\n",
-                "Date: Tue, 15 Nov 1994 08:12:31 GMT\r\n",
-                "Content-Transfer-Encoding: 7bit\r\n",
-                "\r\n",
-                "Be happy!"
-            )
-        );
-        remove_file(eml_file).unwrap();
-    }
-
-    #[cfg(feature = "tokio02")]
     #[tokio::test]
-    async fn file_transport_tokio02() {
-        use lettre::Tokio02Transport;
-
-        let sender = FileTransport::new(temp_dir());
+    async fn file_transport_tokio1() {
+        let sender = AsyncFileTransport::<Tokio1Executor>::new(temp_dir());
         let email = Message::builder()
             .from("NoBody <nobody@domain.tld>".parse().unwrap())
             .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
             .to("Hei <hei@domain.tld>".parse().unwrap())
             .subject("Happy new year")
-            .date("Tue, 15 Nov 1994 08:12:31 GMT".parse().unwrap())
+            .date(default_date())
             .body(String::from("Be happy!"))
             .unwrap();
 
         let result = sender.send(email).await;
         let id = result.unwrap();
 
-        let eml_file = temp_dir().join(format!("{}.eml", id));
+        let eml_file = temp_dir().join(format!("{id}.eml"));
         let eml = read_to_string(&eml_file).unwrap();
 
         assert_eq!(
@@ -155,7 +141,58 @@ mod test {
                 "Reply-To: Yuin <yuin@domain.tld>\r\n",
                 "To: Hei <hei@domain.tld>\r\n",
                 "Subject: Happy new year\r\n",
-                "Date: Tue, 15 Nov 1994 08:12:31 GMT\r\n",
+                "Date: Tue, 15 Nov 1994 08:12:31 +0000\r\n",
+                "Content-Transfer-Encoding: 7bit\r\n",
+                "\r\n",
+                "Be happy!"
+            )
+        );
+        remove_file(eml_file).unwrap();
+    }
+}
+
+#[cfg(test)]
+#[cfg(all(
+    feature = "file-transport",
+    feature = "builder",
+    feature = "async-std1"
+))]
+mod asyncstd_1 {
+    use std::{
+        env::temp_dir,
+        fs::{read_to_string, remove_file},
+    };
+
+    use lettre::{AsyncFileTransport, AsyncStd1Executor, AsyncTransport, Message};
+
+    use crate::default_date;
+
+    #[async_std::test]
+    async fn file_transport_asyncstd1() {
+        let sender = AsyncFileTransport::<AsyncStd1Executor>::new(temp_dir());
+        let email = Message::builder()
+            .from("NoBody <nobody@domain.tld>".parse().unwrap())
+            .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
+            .to("Hei <hei@domain.tld>".parse().unwrap())
+            .subject("Happy new year")
+            .date(default_date())
+            .body(String::from("Be happy!"))
+            .unwrap();
+
+        let result = sender.send(email).await;
+        let id = result.unwrap();
+
+        let eml_file = temp_dir().join(format!("{id}.eml"));
+        let eml = read_to_string(&eml_file).unwrap();
+
+        assert_eq!(
+            eml,
+            concat!(
+                "From: NoBody <nobody@domain.tld>\r\n",
+                "Reply-To: Yuin <yuin@domain.tld>\r\n",
+                "To: Hei <hei@domain.tld>\r\n",
+                "Subject: Happy new year\r\n",
+                "Date: Tue, 15 Nov 1994 08:12:31 +0000\r\n",
                 "Content-Transfer-Encoding: 7bit\r\n",
                 "\r\n",
                 "Be happy!"

tests/transport_sendmail.rs

@@ -1,14 +1,10 @@
 #[cfg(test)]
 #[cfg(all(feature = "sendmail-transport", feature = "builder"))]
-mod test {
-    use lettre::{transport::sendmail::SendmailTransport, Message};
-
-    #[cfg(feature = "tokio02")]
-    use tokio02_crate as tokio;
+mod sync {
+    use lettre::{Message, SendmailTransport, Transport};
 
     #[test]
     fn sendmail_transport() {
-        use lettre::Transport;
         let sender = SendmailTransport::new();
         let email = Message::builder()
             .from("NoBody <nobody@domain.tld>".parse().unwrap())
@@ -19,47 +15,60 @@ mod test {
             .unwrap();
 
         let result = sender.send(&email);
-        println!("{:?}", result);
-        assert!(result.is_ok());
-    }
-
-    #[cfg(feature = "async-std1")]
-    #[async_std::test]
-    async fn sendmail_transport_asyncstd1() {
-        use lettre::AsyncStd1Transport;
-
-        let sender = SendmailTransport::new();
-        let email = Message::builder()
-            .from("NoBody <nobody@domain.tld>".parse().unwrap())
-            .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
-            .to("Hei <hei@domain.tld>".parse().unwrap())
-            .subject("Happy new year")
-            .date("Tue, 15 Nov 1994 08:12:31 GMT".parse().unwrap())
-            .body(String::from("Be happy!"))
-            .unwrap();
-
-        let result = sender.send(email).await;
-        println!("{:?}", result);
-        assert!(result.is_ok());
-    }
-
-    #[cfg(feature = "tokio02")]
-    #[tokio::test]
-    async fn sendmail_transport_tokio02() {
-        use lettre::Tokio02Transport;
-
-        let sender = SendmailTransport::new();
-        let email = Message::builder()
-            .from("NoBody <nobody@domain.tld>".parse().unwrap())
-            .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
-            .to("Hei <hei@domain.tld>".parse().unwrap())
-            .subject("Happy new year")
-            .date("Tue, 15 Nov 1994 08:12:31 GMT".parse().unwrap())
-            .body(String::from("Be happy!"))
-            .unwrap();
-
-        let result = sender.send(email).await;
-        println!("{:?}", result);
+        println!("{result:?}");
+        assert!(result.is_ok());
+    }
+}
+
+#[cfg(test)]
+#[cfg(all(
+    feature = "sendmail-transport",
+    feature = "builder",
+    feature = "tokio1"
+))]
+mod tokio_1 {
+    use lettre::{AsyncSendmailTransport, AsyncTransport, Message, Tokio1Executor};
+    use tokio1_crate as tokio;
+
+    #[tokio::test]
+    async fn sendmail_transport_tokio1() {
+        let sender = AsyncSendmailTransport::<Tokio1Executor>::new();
+        let email = Message::builder()
+            .from("NoBody <nobody@domain.tld>".parse().unwrap())
+            .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
+            .to("Hei <hei@domain.tld>".parse().unwrap())
+            .subject("Happy new year")
+            .body(String::from("Be happy!"))
+            .unwrap();
+
+        let result = sender.send(email).await;
+        println!("{result:?}");
+        assert!(result.is_ok());
+    }
+}
+
+#[cfg(test)]
+#[cfg(all(
+    feature = "sendmail-transport",
+    feature = "builder",
+    feature = "async-std1"
+))]
+mod asyncstd_1 {
+    use lettre::{AsyncSendmailTransport, AsyncStd1Executor, AsyncTransport, Message};
+
+    #[async_std::test]
+    async fn sendmail_transport_asyncstd1() {
+        let sender = AsyncSendmailTransport::<AsyncStd1Executor>::new();
+        let email = Message::builder()
+            .from("NoBody <nobody@domain.tld>".parse().unwrap())
+            .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
+            .to("Hei <hei@domain.tld>".parse().unwrap())
+            .subject("Happy new year")
+            .body(String::from("Be happy!"))
+            .unwrap();
+
+        let result = sender.send(email).await;
+        println!("{result:?}");
         assert!(result.is_ok());
     }
 }

tests/transport_smtp.rs

@@ -1,6 +1,6 @@
 #[cfg(test)]
 #[cfg(all(feature = "smtp-transport", feature = "builder"))]
-mod test {
+mod sync {
     use lettre::{Message, SmtpTransport, Transport};
 
     #[test]
@@ -12,10 +12,61 @@ mod test {
             .subject("Happy new year")
             .body(String::from("Be happy!"))
             .unwrap();
-        SmtpTransport::builder_dangerous("127.0.0.1")
+
+        let sender = SmtpTransport::builder_dangerous("127.0.0.1")
             .port(2525)
-            .build()
-            .send(&email)
-            .unwrap();
+            .build();
+        sender.send(&email).unwrap();
+    }
+}
+
+#[cfg(test)]
+#[cfg(all(feature = "smtp-transport", feature = "builder", feature = "tokio1"))]
+mod tokio_1 {
+    use lettre::{AsyncSmtpTransport, AsyncTransport, Message, Tokio1Executor};
+    use tokio1_crate as tokio;
+
+    #[tokio::test]
+    async fn smtp_transport_simple_tokio1() {
+        let email = Message::builder()
+            .from("NoBody <nobody@domain.tld>".parse().unwrap())
+            .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
+            .to("Hei <hei@domain.tld>".parse().unwrap())
+            .subject("Happy new year")
+            .body(String::from("Be happy!"))
+            .unwrap();
+
+        let sender: AsyncSmtpTransport<Tokio1Executor> =
+            AsyncSmtpTransport::<Tokio1Executor>::builder_dangerous("127.0.0.1")
+                .port(2525)
+                .build();
+        sender.send(email).await.unwrap();
+    }
+}
+
+#[cfg(test)]
+#[cfg(all(
+    feature = "smtp-transport",
+    feature = "builder",
+    feature = "async-std1"
+))]
+mod asyncstd_1 {
+    use lettre::{AsyncSmtpTransport, AsyncStd1Executor, AsyncTransport, Message};
+
+    #[async_std::test]
+    async fn smtp_transport_simple_asyncstd1() {
+        let email = Message::builder()
+            .from("NoBody <nobody@domain.tld>".parse().unwrap())
+            .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
+            .to("Hei <hei@domain.tld>".parse().unwrap())
+            .subject("Happy new year")
+            .body(String::from("Be happy!"))
+            .unwrap();
+
+        let sender: AsyncSmtpTransport<AsyncStd1Executor> =
+            AsyncSmtpTransport::<AsyncStd1Executor>::builder_dangerous("127.0.0.1")
+                .port(2525)
+                .build();
+        sender.send(email).await.unwrap();
     }
 }

tests/transport_smtp_pool.rs

@@ -1,10 +1,9 @@
-#[cfg(all(test, feature = "smtp-transport", feature = "r2d2"))]
-mod test {
-    use lettre::address::Envelope;
-    use lettre::{SmtpTransport, Transport};
-
+#[cfg(all(test, feature = "smtp-transport", feature = "pool"))]
+mod sync {
     use std::{sync::mpsc, thread};
 
+    use lettre::{address::Envelope, SmtpTransport, Transport};
+
     fn envelope() -> Envelope {
         Envelope::new(
             Some("user@localhost".parse().unwrap()),

tests/transport_stub.rs

@@ -1,14 +1,10 @@
 #[cfg(test)]
 #[cfg(feature = "builder")]
-mod test {
-    use lettre::{transport::stub::StubTransport, Message};
-
-    #[cfg(feature = "tokio02")]
-    use tokio02_crate as tokio;
+mod sync {
+    use lettre::{transport::stub::StubTransport, Message, Transport};
 
     #[test]
     fn stub_transport() {
-        use lettre::Transport;
         let sender_ok = StubTransport::new_ok();
         let sender_ko = StubTransport::new_error();
         let email = Message::builder()
@@ -21,45 +17,68 @@ mod test {
 
         sender_ok.send(&email).unwrap();
         sender_ko.send(&email).unwrap_err();
-    }
 
-    #[cfg(feature = "async-std1")]
-    #[async_std::test]
-    async fn stub_transport_asyncstd1() {
-        use lettre::AsyncStd1Transport;
-
-        let sender_ok = StubTransport::new_ok();
-        let sender_ko = StubTransport::new_error();
-        let email = Message::builder()
-            .from("NoBody <nobody@domain.tld>".parse().unwrap())
-            .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
-            .to("Hei <hei@domain.tld>".parse().unwrap())
-            .subject("Happy new year")
-            .date("Tue, 15 Nov 1994 08:12:31 GMT".parse().unwrap())
-            .body(String::from("Be happy!"))
-            .unwrap();
-
-        sender_ok.send(email.clone()).await.unwrap();
-        sender_ko.send(email).await.unwrap_err();
-    }
-
-    #[cfg(feature = "tokio02")]
-    #[tokio::test]
-    async fn stub_transport_tokio02() {
-        use lettre::Tokio02Transport;
-
-        let sender_ok = StubTransport::new_ok();
-        let sender_ko = StubTransport::new_error();
-        let email = Message::builder()
-            .from("NoBody <nobody@domain.tld>".parse().unwrap())
-            .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
-            .to("Hei <hei@domain.tld>".parse().unwrap())
-            .subject("Happy new year")
-            .date("Tue, 15 Nov 1994 08:12:31 GMT".parse().unwrap())
-            .body(String::from("Be happy!"))
-            .unwrap();
-
-        sender_ok.send(email.clone()).await.unwrap();
-        sender_ko.send(email).await.unwrap_err();
+        let expected_messages = [(
+            email.envelope().clone(),
+            String::from_utf8(email.formatted()).unwrap(),
+        )];
+        assert_eq!(sender_ok.messages(), expected_messages);
+    }
+}
+
+#[cfg(test)]
+#[cfg(all(feature = "builder", feature = "tokio1"))]
+mod tokio_1 {
+    use lettre::{transport::stub::AsyncStubTransport, AsyncTransport, Message};
+    use tokio1_crate as tokio;
+
+    #[tokio::test]
+    async fn stub_transport_tokio1() {
+        let sender_ok = AsyncStubTransport::new_ok();
+        let sender_ko = AsyncStubTransport::new_error();
+        let email = Message::builder()
+            .from("NoBody <nobody@domain.tld>".parse().unwrap())
+            .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
+            .to("Hei <hei@domain.tld>".parse().unwrap())
+            .subject("Happy new year")
+            .body(String::from("Be happy!"))
+            .unwrap();
+
+        sender_ok.send(email.clone()).await.unwrap();
+        sender_ko.send(email.clone()).await.unwrap_err();
+
+        let expected_messages = [(
+            email.envelope().clone(),
+            String::from_utf8(email.formatted()).unwrap(),
+        )];
+        assert_eq!(sender_ok.messages().await, expected_messages);
+    }
+}
+
+#[cfg(test)]
+#[cfg(all(feature = "builder", feature = "async-std1"))]
+mod asyncstd_1 {
+    use lettre::{transport::stub::AsyncStubTransport, AsyncTransport, Message};
+
+    #[async_std::test]
+    async fn stub_transport_asyncstd1() {
+        let sender_ok = AsyncStubTransport::new_ok();
+        let sender_ko = AsyncStubTransport::new_error();
+        let email = Message::builder()
+            .from("NoBody <nobody@domain.tld>".parse().unwrap())
+            .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
+            .to("Hei <hei@domain.tld>".parse().unwrap())
+            .subject("Happy new year")
+            .body(String::from("Be happy!"))
+            .unwrap();
+
+        sender_ok.send(email.clone()).await.unwrap();
+        sender_ko.send(email.clone()).await.unwrap_err();
+
+        let expected_messages = [(
+            email.envelope().clone(),
+            String::from_utf8(email.formatted()).unwrap(),
+        )];
+        assert_eq!(sender_ok.messages().await, expected_messages);
     }
 }