regression

Bumps [tokio](https://github.com/tokio-rs/tokio) from 1.44.1 to 1.44.2.
- [Release notes](https://github.com/tokio-rs/tokio/releases)
- [Commits](https://github.com/tokio-rs/tokio/compare/tokio-1.44.1...tokio-1.44.2)

---
updated-dependencies:
- dependency-name: tokio
  dependency-version: 1.44.2
  dependency-type: indirect
...

Signed-off-by: dependabot[bot] <support@github.com>
Co-authored-by: dependabot[bot] <49699333+dependabot[bot]@users.noreply.github.com>

.editorconfig

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

.github/workflows/test.yml

@@ -13,16 +13,16 @@ env:
 
 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
@@ -34,7 +34,7 @@ jobs:
 
     steps:
       - name: Checkout
-        uses: actions/checkout@v2
+        uses: actions/checkout@v4
 
       - name: Install rust
         run: |
@@ -50,25 +50,19 @@ jobs:
 
     steps:
       - name: Checkout
-        uses: actions/checkout@v2
+        uses: actions/checkout@v4
-
-      - name: Setup cache
-        uses: actions/cache@v2
-        with:
-          path: |
-            ~/.cargo/registry
-            ~/.cargo/git
-            target
-          key: ${{ runner.os }}-cargo-check
 
       - 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 }}
@@ -81,27 +75,21 @@ jobs:
             rust: stable
           - name: beta
             rust: beta
-          - name: 1.52.1
+          - name: '1.74'
-            rust: 1.52.1
+            rust: '1.74'
 
     steps:
       - name: Checkout
-        uses: actions/checkout@v2
+        uses: actions/checkout@v4
-
-      - name: Setup cache
-        uses: actions/cache@v2
-        with:
-          path: |
-            ~/.cargo/registry
-            ~/.cargo/git
-            target
-          key: ${{ runner.os }}-cargo-test-${{ matrix.rust }}
 
       - name: Install rust
         run: |
           rustup default ${{ matrix.rust }}
           rustup update --no-self-update ${{ matrix.rust }}
 
+      - name: Setup cache
+        uses: Swatinem/rust-cache@v2
+
       - name: Install postfix
         run: |
           DEBIAN_FRONTEND=noninteractive sudo apt-get update
@@ -110,20 +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
+      - name: Test with all features (-native-tls)
-        run: cargo test --all-features
+        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 +1,487 @@
+<a name="v0.11.16"></a>
+### v0.11.16 (2025-05-12)
+
+#### Features
+
+* Always implement `Clone` for `AsyncFileTransport` ([#1075])
+
+#### Changes
+
+* `Tls`, `CertificateStore`, `TlsParameters`, `TlsParametersBuilder`, `Certificate` and `Identity`
+  are now marked as deprecated when no TLS backend is enabled. They will be properly feature gated
+  in lettre v0.12 ([#1084])
+
+#### Misc
+
+* Gate `web-time` behind `cfg(target_arch = "wasm32")]` ([#1086])
+* Add missing `#[doc(cfg(...))]` attributes ([#1086])
+* Upgrade `webpki-roots` to v1 ([#1088])
+* Cleanup internal `TlsParameters` and `(Async)NetworkStream` structures ([#1082])
+* Feature gate internal `TransportBuilder::tls` to avoid recursive call site warnings ([#1083])
+* Fix workaround for embedding cargo script in rustdoc output ([#1077])
+* Fix `clippy::io_other_error` warnings ([#1078])
+* Upgrade semver compatible dependencies ([#1076], [#1079], [#1080])
+
+[#1075]: https://github.com/lettre/lettre/pull/1075
+[#1076]: https://github.com/lettre/lettre/pull/1076
+[#1077]: https://github.com/lettre/lettre/pull/1077
+[#1078]: https://github.com/lettre/lettre/pull/1078
+[#1079]: https://github.com/lettre/lettre/pull/1079
+[#1080]: https://github.com/lettre/lettre/pull/1080
+[#1082]: https://github.com/lettre/lettre/pull/1082
+[#1083]: https://github.com/lettre/lettre/pull/1083
+[#1084]: https://github.com/lettre/lettre/pull/1084
+[#1086]: https://github.com/lettre/lettre/pull/1086
+[#1088]: https://github.com/lettre/lettre/pull/1088
+
+<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 1.52.1
+* 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,
@@ -29,6 +505,7 @@ 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
@@ -53,7 +530,7 @@ 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>

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-rc.4"
+version = "0.11.16"
 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" }
@@ -18,32 +19,40 @@ is-it-maintained-open-issues = { repository = "lettre/lettre" }
 maintenance = { status = "actively-developed" }
 
 [dependencies]
-idna = "0.2"
+email_address = { version = "0.2.1", default-features = false }
-once_cell = "1"
+chumsky = "0.9"
-tracing = { version = "0.1.16", default-features = false, features = ["std"], optional = true } # feature
+idna = "1"
+
+## tracing support
+tracing = { version = "0.1.16", default-features = false, features = ["std"], optional = true }
 
 # builder
 httpdate = { version = "1", optional = true }
 mime = { version = "0.3.4", optional = true }
-fastrand = { version = "1.4", optional = true }
+fastrand = { version = "2.0", optional = true }
-quoted_printable = { version = "0.4", optional = true }
+quoted_printable = { version = "0.5", optional = true }
-base64 = { version = "0.13", optional = true }
+base64 = { version = "0.22", optional = true }
-regex = { version = "1", default-features = false, features = ["std", "unicode-case"] }
+email-encoding = { version = "0.4", optional = true }
 
 # file transport
-uuid = { version = "0.8", features = ["v4"], optional = true }
+uuid = { version = "1", features = ["v4"], optional = true }
-serde = { version = "1", optional = true, features = ["derive"] }
+serde = { version = "1.0.110", features = ["derive"], optional = true }
 serde_json = { version = "1", optional = true }
 
-# smtp
+# smtp-transport
-nom = { version = "7", optional = true }
+nom = { version = "8", optional = true }
-hostname = { version = "0.3", optional = true } # feature
+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
+native-tls = { version = "0.2.9", optional = true } # feature
-rustls = { version = "0.20", features = ["dangerous_configuration"], optional = true }
+rustls = { version = "0.23.18", default-features = false, features = ["logging", "std", "tls12"], optional = true }
-rustls-pemfile = { version = "0.2.1", optional = true }
+rustls-platform-verifier = { version = "0.6.0", optional = true }
-webpki-roots = { version = "0.22", optional = true }
+rustls-native-certs = { version = "0.8", optional = true }
+webpki-roots = { version = "1.0.0", optional = true }
+boring = { version = "4", optional = true }
 
 # async
 futures-io = { version = "0.3.7", optional = true }
@@ -51,56 +60,95 @@ 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-std = { version = "1.8", optional = true }
-#async-native-tls = { version = "0.3.3", optional = true }
+futures-rustls = { version = "0.26", default-features = false, features = ["logging", "tls12"], optional = true }
-futures-rustls = { version = "0.22", optional = true }
 
 ## tokio
-tokio1_crate = { package = "tokio", version = "1", features = ["fs", "process", "time", "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 = "0.23", 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 }
+
+[target.'cfg(target_arch = "wasm32")'.dependencies]
+## web-time for wasm support
+web-time = { version = "1.1.0", optional = true }
 
 [dev-dependencies]
-criterion = "0.3"
+pretty_assertions = "1"
-tracing-subscriber = "0.2.10"
+criterion = "0.5"
+tracing = { version = "0.1.16", default-features = false, features = ["std"] }
+tracing-subscriber = "0.3"
 glob = "0.3"
 walkdir = "2"
 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 = ["smtp-transport", "pool", "native-tls", "hostname", "builder"]
-builder = ["httpdate", "mime", "base64", "fastrand", "quoted_printable"]
+builder = ["dep:httpdate", "dep:mime", "dep:fastrand", "dep:quoted_printable", "dep:email-encoding"]
-mime03 = ["mime"]
+mime03 = ["dep:mime"]
 
 # transports
-file-transport = ["uuid"]
+file-transport = ["dep:uuid", "tokio1_crate?/fs", "tokio1_crate?/io-util"]
-file-transport-envelope = ["serde", "serde_json", "file-transport"]
+file-transport-envelope = ["serde", "dep:serde_json", "file-transport"]
-sendmail-transport = []
+sendmail-transport = ["tokio1_crate?/process", "tokio1_crate?/io-util", "async-std?/unstable"]
-smtp-transport = ["base64", "nom"]
+smtp-transport = ["dep:base64", "dep:nom", "dep:socket2", "dep:url", "dep:percent-encoding", "tokio1_crate?/rt", "tokio1_crate?/time", "tokio1_crate?/net"]
 
-pool = ["futures-util"]
+pool = ["dep:futures-util"]
 
-rustls-tls = ["webpki-roots", "rustls", "rustls-pemfile"]
+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 = ["dep:async-std", "dep:async-trait", "dep:futures-io", "dep:futures-util"]
-#async-std1-native-tls = ["async-std1", "native-tls", "async-native-tls"]
+async-std1-rustls = ["async-std1", "rustls", "dep:futures-rustls"]
-async-std1-rustls-tls = ["async-std1", "rustls-tls", "futures-rustls"]
+# deprecated
-tokio1 = ["tokio1_crate", "async-trait", "futures-io", "futures-util"]
+async-std1-rustls-tls = ["async-std1-rustls", "rustls-tls"]
-tokio1-native-tls = ["tokio1", "native-tls", "tokio1_native_tls_crate"]
+tokio1 = ["dep:tokio1_crate", "dep:async-trait", "dep:futures-io", "dep:futures-util"]
-tokio1-rustls-tls = ["tokio1", "rustls-tls", "tokio1_rustls"]
+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", "--cfg", "lettre_ignore_tls_mismatch"]
 
+[[example]]
+name = "autoconfigure"
+required-features = ["smtp-transport", "native-tls"]
+
 [[example]]
 name = "basic_html"
 required-features = ["file-transport", "builder"]

LICENSE

@@ -1,5 +1,5 @@
-Copyright (c) 2014-2020 Alexis Mousset <contact@amousset.me>
+Copyright (c) 2014-2024 Alexis Mousset <contact@amousset.me>
-Copyright (c) 2019-2020 Paolo Barbolini <paolo@paolo565.org>
+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

@@ -28,27 +28,14 @@
 </div>
 
 <div align="center">
-  <a href="https://deps.rs/crate/lettre/0.10.0-rc.4">
+  <a href="https://deps.rs/crate/lettre/0.11.16">
-    <img src="https://deps.rs/crate/lettre/0.10.0-rc.4/status.svg"
+    <img src="https://deps.rs/crate/lettre/0.11.16/status.svg"
       alt="dependency status" />
   </a>
 </div>
 
 ---
 
-**NOTE**: this readme refers to the 0.10 version of lettre, which is
-in release candidate state. Use the [`v0.9.x`](https://github.com/lettre/lettre/tree/v0.9.x)
-branch for the previous stable release.
-
-0.10 is already widely used and is already thought to be more reliable than 0.9, so it should generally be used
-for new projects.
-
-We'd love to hear your feedback about 0.10 design and APIs before final release!
-Start a [discussion](https://github.com/lettre/lettre/discussions) in the repository, whether for
-feedback or if you need help or advice using or upgrading lettre 0.10.
-
----
-
 ## Features
 
 Lettre provides the following features:
@@ -63,51 +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 1.52.1 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-rc.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()
+fn main() {
-    .from("NoBody <nobody@domain.tld>".parse().unwrap())
+    let email = Message::builder()
-    .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
+        .from(Mailbox::new("NoBody".to_owned(), "nobody@domain.tld".parse().unwrap()))
-    .to("Hei <hei@domain.tld>".parse().unwrap())
+        .reply_to(Mailbox::new("Yuin".to_owned(), "yuin@domain.tld".parse().unwrap()))
+        .to(Mailbox::new("Hei".to_owned(), "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
+    // Open a remote connection to gmail
-let mailer = SmtpTransport::relay("smtp.gmail.com")
+    let mailer = SmtpTransport::relay("smtp.gmail.com")
         .unwrap()
         .credentials(creds)
         .build();
 
-// Send the email
+    // Send the email
-match mailer.send(&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:?}"),
+    }
 }
 ```
 
+## 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. If you have python installed
-such a server can be launched with `python -m smtpd -n -c DebuggingServer localhost:2525`
+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/asyncstd1_smtp_starttls.rs

@@ -1,6 +1,6 @@
 use lettre::{
-    transport::smtp::authentication::Credentials, AsyncSmtpTransport, AsyncStd1Executor,
+    message::header::ContentType, transport::smtp::authentication::Credentials, AsyncSmtpTransport,
-    AsyncTransport, Message,
+    AsyncStd1Executor, AsyncTransport, Message,
 };
 
 #[async_std::main]
@@ -12,10 +12,11 @@ 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<AsyncStd1Executor> =
@@ -27,6 +28,6 @@ async fn main() {
     // 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, AsyncStd1Executor,
+    message::header::ContentType, transport::smtp::authentication::Credentials, AsyncSmtpTransport,
-    AsyncTransport, Message,
+    AsyncStd1Executor, AsyncTransport, Message,
 };
 
 #[async_std::main]
@@ -12,10 +12,11 @@ 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<AsyncStd1Executor> =
@@ -27,6 +28,6 @@ async fn main() {
     // 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/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

@@ -1,6 +1,7 @@
 use std::fs;
 
 use lettre::{
+    message::header::ContentType,
     transport::smtp::{
         authentication::Credentials,
         client::{Certificate, Tls, TlsParameters},
@@ -16,18 +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 tls = TlsParameters::builder("smtp.server.com".to_string())
+    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")
@@ -39,6 +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/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, AsyncTransport, Message,
+    message::header::ContentType, transport::smtp::authentication::Credentials, AsyncSmtpTransport,
-    Tokio1Executor,
+    AsyncTransport, Message, Tokio1Executor,
 };
+use tokio1_crate as tokio;
 
 #[tokio::main]
 async fn main() {
@@ -17,10 +16,11 @@ 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<Tokio1Executor> =
@@ -32,6 +32,6 @@ async fn main() {
     // 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, AsyncTransport, Message,
+    message::header::ContentType, transport::smtp::authentication::Credentials, AsyncSmtpTransport,
-    Tokio1Executor,
+    AsyncTransport, Message, Tokio1Executor,
 };
+use tokio1_crate as tokio;
 
 #[tokio::main]
 async fn main() {
@@ -17,10 +16,11 @@ 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<Tokio1Executor> =
@@ -32,6 +32,6 @@ async fn main() {
     // 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};
@@ -17,11 +14,71 @@ 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.
     ///
@@ -106,6 +163,7 @@ impl Envelope {
 }
 
 #[cfg(feature = "builder")]
+#[cfg_attr(docsrs, doc(cfg(feature = "builder")))]
 impl TryFrom<&Headers> for Envelope {
     type Error = Error;
 

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},
@@ -12,11 +8,14 @@ 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
 ///
@@ -55,20 +54,6 @@ pub struct Address {
     at_start: usize,
 }
 
-// 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.
     ///
@@ -126,7 +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)
@@ -142,17 +127,20 @@ 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) {
+        // IP
-            if let Some(cap) = caps.get(1) {
+        let ip = domain
-                if cap.as_str().parse::<IpAddr>().is_ok() {
+            .strip_prefix('[')
+            .and_then(|ip| ip.strip_suffix(']'))
+            .unwrap_or(domain);
+
+        if ip.parse::<IpAddr>().is_ok() {
             return Ok(());
         }
-            }
-        }
 
         Err(AddressError::InvalidDomain)
     }
@@ -196,7 +184,7 @@ where
         let domain = domain.as_ref();
         Address::check_domain(domain)?;
 
-        let serialized = format!("{}@{}", user, domain);
+        let serialized = format!("{user}@{domain}");
         Ok(Address {
             serialized,
             at_start: user.len(),
@@ -238,7 +226,8 @@ fn check_address(val: &str) -> Result<usize, AddressError> {
     Ok(user.len())
 }
 
-#[derive(Debug, PartialEq, Clone, Copy)]
+#[derive(Debug, PartialEq, Eq, Clone, Copy)]
+#[non_exhaustive]
 /// Errors in email addresses parsing
 pub enum AddressError {
     /// Missing domain or user
@@ -249,6 +238,8 @@ pub enum AddressError {
     InvalidUser,
     /// Invalid email domain
     InvalidDomain,
+    /// Invalid input found
+    InvalidInput,
 }
 
 impl Error for AddressError {}
@@ -260,6 +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::InvalidInput => f.write_str("Invalid input"),
         }
     }
 }
@@ -269,7 +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();
@@ -279,4 +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/executor.rs

@@ -1,7 +1,3 @@
-use async_trait::async_trait;
-#[cfg(all(feature = "smtp-transport", feature = "async-std1"))]
-use futures_util::future::BoxFuture;
-
 use std::fmt::Debug;
 #[cfg(feature = "smtp-transport")]
 use std::future::Future;
@@ -12,6 +8,10 @@ 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")
@@ -45,6 +45,7 @@ use crate::transport::smtp::Error;
 #[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;
@@ -82,8 +83,8 @@ pub trait Executor: Debug + Send + Sync + 'static + private::Sealed {
 #[doc(hidden)]
 #[cfg(feature = "smtp-transport")]
 #[async_trait]
-pub trait SpawnHandle: Debug + Send + Sync + 'static + private::Sealed {
+pub(crate) trait SpawnHandle: Debug + Send + Sync + 'static + private::Sealed {
-    async fn shutdown(self);
+    async fn shutdown(&self);
 }
 
 /// Async [`Executor`] using `tokio` `1.x`
@@ -109,7 +110,6 @@ impl Executor for Tokio1Executor {
     #[cfg(feature = "smtp-transport")]
     type Sleep = tokio1_crate::time::Sleep;
 
-    #[doc(hidden)]
     #[cfg(feature = "smtp-transport")]
     fn spawn<F>(fut: F) -> Self::Handle
     where
@@ -119,13 +119,11 @@ impl Executor for Tokio1Executor {
         tokio1_crate::spawn(fut)
     }
 
-    #[doc(hidden)]
     #[cfg(feature = "smtp-transport")]
     fn sleep(duration: Duration) -> Self::Sleep {
         tokio1_crate::time::sleep(duration)
     }
 
-    #[doc(hidden)]
     #[cfg(feature = "smtp-transport")]
     async fn connect(
         hostname: &str,
@@ -136,8 +134,8 @@ impl Executor for Tokio1Executor {
     ) -> Result<AsyncSmtpConnection, Error> {
         #[allow(clippy::match_single_binding)]
         let tls_parameters = match tls {
-            #[cfg(any(feature = "tokio1-native-tls", feature = "tokio1-rustls-tls"))]
+            #[cfg(any(feature = "tokio1-native-tls", feature = "tokio1-rustls"))]
-            Tls::Wrapper(ref tls_parameters) => Some(tls_parameters.clone()),
+            Tls::Wrapper(tls_parameters) => Some(tls_parameters.clone()),
             _ => None,
         };
         #[allow(unused_mut)]
@@ -146,17 +144,18 @@ impl Executor for Tokio1Executor {
             timeout,
             hello_name,
             tls_parameters,
+            None,
         )
         .await?;
 
-        #[cfg(any(feature = "tokio1-native-tls", feature = "tokio1-rustls-tls"))]
+        #[cfg(any(feature = "tokio1-native-tls", feature = "tokio1-rustls"))]
         match tls {
-            Tls::Opportunistic(ref tls_parameters) => {
+            Tls::Opportunistic(tls_parameters) => {
                 if conn.can_starttls() {
                     conn.starttls(tls_parameters.clone(), hello_name).await?;
                 }
             }
-            Tls::Required(ref tls_parameters) => {
+            Tls::Required(tls_parameters) => {
                 conn.starttls(tls_parameters.clone(), hello_name).await?;
             }
             _ => (),
@@ -165,13 +164,11 @@ impl Executor for Tokio1Executor {
         Ok(conn)
     }
 
-    #[doc(hidden)]
     #[cfg(feature = "file-transport-envelope")]
     async fn fs_read(path: &Path) -> IoResult<Vec<u8>> {
         tokio1_crate::fs::read(path).await
     }
 
-    #[doc(hidden)]
     #[cfg(feature = "file-transport")]
     async fn fs_write(path: &Path, contents: &[u8]) -> IoResult<()> {
         tokio1_crate::fs::write(path, contents).await
@@ -181,7 +178,7 @@ impl Executor for Tokio1Executor {
 #[cfg(all(feature = "smtp-transport", feature = "tokio1"))]
 #[async_trait]
 impl SpawnHandle for tokio1_crate::task::JoinHandle<()> {
-    async fn shutdown(self) {
+    async fn shutdown(&self) {
         self.abort();
     }
 }
@@ -205,28 +202,27 @@ pub struct AsyncStd1Executor;
 #[cfg(feature = "async-std1")]
 impl Executor for AsyncStd1Executor {
     #[cfg(feature = "smtp-transport")]
-    type Handle = async_std::task::JoinHandle<()>;
+    type Handle = futures_util::future::AbortHandle;
     #[cfg(feature = "smtp-transport")]
     type Sleep = BoxFuture<'static, ()>;
 
-    #[doc(hidden)]
     #[cfg(feature = "smtp-transport")]
     fn spawn<F>(fut: F) -> Self::Handle
     where
         F: Future<Output = ()> + Send + 'static,
         F::Output: Send + 'static,
     {
-        async_std::task::spawn(fut)
+        let (handle, registration) = futures_util::future::AbortHandle::new_pair();
+        async_std::task::spawn(futures_util::future::Abortable::new(fut, registration));
+        handle
     }
 
-    #[doc(hidden)]
     #[cfg(feature = "smtp-transport")]
     fn sleep(duration: Duration) -> Self::Sleep {
-        let fut = async move { async_std::task::sleep(duration).await };
+        let fut = async_std::task::sleep(duration);
         Box::pin(fut)
     }
 
-    #[doc(hidden)]
     #[cfg(feature = "smtp-transport")]
     async fn connect(
         hostname: &str,
@@ -237,8 +233,8 @@ impl Executor for AsyncStd1Executor {
     ) -> 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"))]
+            #[cfg(feature = "async-std1-rustls")]
-            Tls::Wrapper(ref tls_parameters) => Some(tls_parameters.clone()),
+            Tls::Wrapper(tls_parameters) => Some(tls_parameters.clone()),
             _ => None,
         };
         #[allow(unused_mut)]
@@ -250,14 +246,14 @@ impl Executor for AsyncStd1Executor {
         )
         .await?;
 
-        #[cfg(any(feature = "async-std1-native-tls", feature = "async-std1-rustls-tls"))]
+        #[cfg(feature = "async-std1-rustls")]
         match tls {
-            Tls::Opportunistic(ref tls_parameters) => {
+            Tls::Opportunistic(tls_parameters) => {
                 if conn.can_starttls() {
                     conn.starttls(tls_parameters.clone(), hello_name).await?;
                 }
             }
-            Tls::Required(ref tls_parameters) => {
+            Tls::Required(tls_parameters) => {
                 conn.starttls(tls_parameters.clone(), hello_name).await?;
             }
             _ => (),
@@ -266,13 +262,11 @@ impl Executor for AsyncStd1Executor {
         Ok(conn)
     }
 
-    #[doc(hidden)]
     #[cfg(feature = "file-transport-envelope")]
     async fn fs_read(path: &Path) -> IoResult<Vec<u8>> {
         async_std::fs::read(path).await
     }
 
-    #[doc(hidden)]
     #[cfg(feature = "file-transport")]
     async fn fs_write(path: &Path, contents: &[u8]) -> IoResult<()> {
         async_std::fs::write(path, contents).await
@@ -281,26 +275,24 @@ impl Executor for AsyncStd1Executor {
 
 #[cfg(all(feature = "smtp-transport", feature = "async-std1"))]
 #[async_trait]
-impl SpawnHandle for async_std::task::JoinHandle<()> {
+impl SpawnHandle for futures_util::future::AbortHandle {
-    async fn shutdown(self) {
+    async fn shutdown(&self) {
-        self.cancel().await;
+        self.abort();
     }
 }
 
 mod private {
-    use super::*;
-
     pub trait Sealed {}
 
     #[cfg(feature = "tokio1")]
-    impl Sealed for Tokio1Executor {}
+    impl Sealed for super::Tokio1Executor {}
 
     #[cfg(feature = "async-std1")]
-    impl Sealed for AsyncStd1Executor {}
+    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 async_std::task::JoinHandle<()> {}
+    impl Sealed for futures_util::future::AbortHandle {}
 }

src/lib.rs

@@ -6,7 +6,7 @@
 //! * Secure defaults
 //! * Async support
 //!
-//! Lettre requires Rust 1.52.1 or newer.
+//! Lettre requires Rust 1.74 or newer.
 //!
 //! ## Features
 //!
@@ -34,22 +34,79 @@
 //!
 //! _Secure SMTP connections using TLS from the `native-tls` crate_
 //!
-//! Uses schannel on Windows, Security-Framework on macOS, and OpenSSL on Linux.
+//! 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-tls` crate_
+//! _Secure SMTP connections using TLS from the `rustls` crate_
 //!
-//! Rustls uses [ring] as the cryptography implementation. As a result, [not all Rust's targets are supported][ring-support].
+//! * **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-tls**: TLS support for the synchronous version of the API
+//! ##### rustls crypto backends
-//! * **tokio1-rustls-tls**: TLS support for the `tokio1` async version of the API
+//!
-//! * **async-std1-rustls-tls**: TLS support for the `async-std1` async version of the API
+//! _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-platform-verifier**: verify TLS certificate using the OS's native certificate store (see [`rustls-platform-verifier`])
+//! * **rustls-native-certs**: verify TLS certificates using the platform's native certificate store (see [`rustls-native-certs`]) - when in doubt use `rustls-platform-verifier`
+//! * **webpki-roots**: verify TLS certificates against Mozilla's root certificates (see [`webpki-roots`])
+//!
+//! The following packages will need to be installed in order for the build
+//! stage and the compiled program to run properly.
+//!
+//! | Verification backend       | Distro       | Build-time packages        | Runtime packages             |
+//! | ---------------------      | ------------ | -------------------------- | ---------------------------- |
+//! | `rustls-platform-verifier` | Debian       | none                       | `ca-certificates`            |
+//! | `rustls-platform-verifier` | Alpine Linux | none                       | `ca-certificates`            |
+//! | `rustls-native-certs`      | Debian       | none                       | `ca-certificates`            |
+//! | `rustls-native-certs`      | Alpine Linux | none                       | `ca-certificates`            |
+//! | `webpki-roots`             | any          | none                       | none                         |
 //!
 //! ### Sendmail transport
 //!
@@ -85,6 +142,8 @@
 //! * **serde**: Serialization/Deserialization of entities
 //! * **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
@@ -92,92 +151,142 @@
 //! [`ContentType`]: crate::message::header::ContentType
 //! [tokio]: https://docs.rs/tokio/1
 //! [async-std]: https://docs.rs/async-std/1
-//! [ring]: https://github.com/briansmith/ring#ring
+//! [AWS-LC]: https://github.com/aws/aws-lc
-//! [ring-support]: https://github.com/briansmith/ring#online-automated-testing
+//! [`aws-lc-rs`]: https://crates.io/crates/aws-lc-rs
+//! [`ring`]: https://crates.io/crates/ring
+//! [`rustls-platform-verifier`]: https://crates.io/crates/rustls-platform-verifier
+//! [`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-rc.4")]
+#![doc(html_root_url = "https://docs.rs/crate/lettre/0.11.16")]
 #![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-platform-verifier"),
+        not(feature = "rustls-native-certs"),
+        not(feature = "webpki-roots")
+    ))]
+    compile_error!(
+        "feature `rustls` also requires either the `rustls-platform-verifier`, 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'd like to use rustls make sure that the `native-tls` hasn't been enabled by mistake (you may need to import lettre without default features)
+    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.
-If you're building a library which depends on lettre import it without default features and enable just the features you need.");
+    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 = "rustls-tls",
+        feature = "boring-tls",
-        not(feature = "tokio1-rustls-tls")
+        not(feature = "tokio1-boring-tls")
     ))]
-    compile_error!("Lettre is being built with the `tokio1` and the `rustls-tls` features, but the `tokio1-rustls-tls` feature hasn't been turned on.
+    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 native-tls make sure that the `rustls-tls` hasn't been enabled by mistake.
+    If you'd like to use `boring-tls` make sure that the `rustls` feature hasn't been enabled by mistake.
-If you're building a library which depends on lettre import it without default features and enable just the features you need.");
+    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"))]
-    #[cfg(all(
-        feature = "async-std1",
-        feature = "native-tls",
-        not(feature = "async-std1-native-tls")
-    ))]
-    compile_error!("Lettre is being built with the `async-std1` and the `native-tls` features, but the `async-std1-native-tls` feature hasn't been turned on.
-    If you'd like to use rustls make sure that the `native-tls` hasn't been enabled by mistake (you may need to import lettre without default features)
-    If you're building a library which depends on lettre import it without default features and enable just the features you need.");
-    */
-    #[cfg(all(
-        feature = "async-std1",
-        feature = "native-tls",
-        not(feature = "async-std1-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'd like to use rustls make sure that the `native-tls` hasn't been enabled by mistake (you may need to import lettre without default features)
+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.
-If you're building a library which depends on lettre import lettre without default features and enable just the features you need.");
+Make sure to apply the same to any of your crate dependencies that use the `lettre` crate.");
 
     #[cfg(all(
         feature = "async-std1",
-        feature = "rustls-tls",
+        feature = "rustls",
-        not(feature = "async-std1-rustls-tls")
+        not(feature = "async-std1-rustls")
     ))]
-    compile_error!("Lettre is being built with the `async-std1` and the `rustls-tls` features, but the `async-std1-rustls-tls` feature hasn't been turned on.
+    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-tls` hasn't been enabled by mistake (you may need to import lettre without default features)
+If you'd like to use `native-tls` make sure that the `rustls` hasn't been enabled by mistake.
-If you're building a library which depends on lettre import it without default features and enable just the features you need.");
+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;
 
+use std::error::Error as StdError;
+
 #[cfg(feature = "async-std1")]
 pub use self::executor::AsyncStd1Executor;
-#[cfg(all(any(feature = "tokio1", feature = "async-std1")))]
+#[cfg(any(feature = "tokio1", feature = "async-std1"))]
 pub use self::executor::Executor;
 #[cfg(feature = "tokio1")]
 pub use self::executor::Tokio1Executor;
-#[cfg(all(any(feature = "tokio1", feature = "async-std1")))]
+#[cfg(any(feature = "tokio1", feature = "async-std1"))]
 #[doc(inline)]
 pub use self::transport::AsyncTransport;
 pub use crate::address::Address;
@@ -207,21 +316,17 @@ pub use crate::transport::sendmail::SendmailTransport;
     any(feature = "tokio1", feature = "async-std1")
 ))]
 pub use crate::transport::smtp::AsyncSmtpTransport;
+#[cfg(feature = "smtp-transport")]
+pub use crate::transport::smtp::SmtpTransport;
 #[doc(inline)]
 pub use crate::transport::Transport;
 use crate::{address::Envelope, error::Error};
 
-#[cfg(feature = "smtp-transport")]
-pub use crate::transport::smtp::SmtpTransport;
-use std::error::Error as StdError;
-
 pub(crate) type BoxError = Box<dyn StdError + Send + Sync>;
 
 #[cfg(test)]
 #[cfg(feature = "builder")]
 mod test {
-    use std::convert::TryFrom;
-
     use super::*;
     use crate::message::{header, header::Headers, Mailbox, Mailboxes};
 

src/message/attachment.rs

@@ -13,9 +13,9 @@ pub struct Attachment {
 
 #[derive(Clone)]
 enum Disposition {
-    /// file name
+    /// File name
     Attached(String),
-    /// content id
+    /// Content id
     Inline(String),
 }
 
@@ -29,7 +29,7 @@ impl Attachment {
     /// # use std::error::Error;
     /// use std::fs;
     ///
-    /// use lettre::message::{Attachment, header::ContentType};
+    /// use lettre::message::{header::ContentType, Attachment};
     ///
     /// # fn main() -> Result<(), Box<dyn Error>> {
     /// let filename = String::from("invoice.pdf");
@@ -64,7 +64,7 @@ impl Attachment {
     /// # use std::error::Error;
     /// use std::fs;
     ///
-    /// use lettre::message::{Attachment, header::ContentType};
+    /// use lettre::message::{header::ContentType, Attachment};
     ///
     /// # fn main() -> Result<(), Box<dyn Error>> {
     /// let content_id = String::from("123");
@@ -96,7 +96,7 @@ impl Attachment {
                 builder.header(header::ContentDisposition::attachment(&filename))
             }
             Disposition::Inline(content_id) => builder
-                .header(header::ContentId::from(format!("<{}>", content_id)))
+                .header(header::ContentId::from(format!("<{content_id}>")))
                 .header(header::ContentDisposition::inline()),
         };
         builder = builder.header(content_type);

src/message/body.rs

@@ -1,8 +1,4 @@
-use std::{
+use std::{mem, ops::Deref};
-    io::{self, Write},
-    mem,
-    ops::Deref,
-};
 
 use crate::message::header::ContentTransferEncoding;
 
@@ -41,7 +37,7 @@ impl Body {
     pub fn new<B: Into<MaybeString>>(buf: B) -> Self {
         let mut buf: MaybeString = buf.into();
 
-        let encoding = buf.encoding();
+        let encoding = buf.encoding(false);
         buf.encode_crlf();
         Self::new_impl(buf.into(), encoding)
     }
@@ -61,7 +57,22 @@ impl Body {
     ) -> Result<Self, Vec<u8>> {
         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());
         }
 
@@ -91,36 +102,13 @@ impl Body {
                 Self::dangerous_pre_encoded(encoded, ContentTransferEncoding::QuotedPrintable)
             }
             ContentTransferEncoding::Base64 => {
-                let base64_len = buf.len() * 4 / 3 + 4;
+                let len = email_encoding::body::base64::encoded_len(buf.len());
-                let base64_endings_len = base64_len + base64_len / LINE_MAX_LENGTH;
 
-                let mut out = Vec::with_capacity(base64_endings_len);
+                let mut out = String::with_capacity(len);
-                {
+                email_encoding::body::base64::encode(&buf, &mut out)
-                    let writer = LineWrappingWriter::new(&mut out, LINE_MAX_LENGTH);
+                    .expect("encode body as base64");
-                    let mut writer = base64::write::EncoderWriter::new(writer, base64::STANDARD);
 
-                    // TODO: use writer.write_all(self.as_ref()).expect("base64 encoding never fails");
+                Self::dangerous_pre_encoded(out.into_bytes(), ContentTransferEncoding::Base64)
-
-                    // 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)
             }
         }
     }
@@ -153,21 +141,20 @@ 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
+    /// The `binary` encoding is never returned
-    /// characters, with no lines longer than 1000 characters, then 7bit
+    fn encoding(&self, supports_utf8: bool) -> ContentTransferEncoding {
-    /// encoding will be used, else quoted-printable will be chosen.
+        use email_encoding::body::Encoding;
-    ///
+
-    /// If the `MaybeString` was instead created from a `Vec<u8>`, base64 encoding is always
+        let output = match self {
-    /// chosen.
+            Self::String(s) => Encoding::choose(s.as_str(), supports_utf8),
-    ///
+            Self::Binary(b) => Encoding::choose(b.as_slice(), supports_utf8),
-    /// `8bit` and `binary` encodings are never returned, as they may not be
+        };
-    /// supported by all SMTP servers.
+
-    pub fn encoding(&self) -> ContentTransferEncoding {
+        match output {
-        match &self {
+            Encoding::SevenBit => ContentTransferEncoding::SevenBit,
-            Self::String(s) if is_7bit_encoded(s.as_ref()) => ContentTransferEncoding::SevenBit,
+            Encoding::EightBit => ContentTransferEncoding::EightBit,
-            // TODO: consider when base64 would be a better option because of output size
+            Encoding::QuotedPrintable => ContentTransferEncoding::QuotedPrintable,
-            Self::String(_) => ContentTransferEncoding::QuotedPrintable,
+            Encoding::Base64 => ContentTransferEncoding::Base64,
-            Self::Binary(_) => ContentTransferEncoding::Base64,
         }
     }
 
@@ -178,18 +165,6 @@ impl MaybeString {
             Self::Binary(_) => {}
         }
     }
-
-    /// 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,
-        }
-    }
 }
 
 /// A trait for something that takes an encoded [`Body`].
@@ -273,73 +248,6 @@ impl Deref for MaybeString {
     }
 }
 
-/// Checks whether it contains only US-ASCII characters,
-/// and no lines are longer than 1000 characters including the `\n` character.
-///
-/// Most efficient content encoding available
-fn is_7bit_encoded(buf: &[u8]) -> bool {
-    buf.is_ascii() && !contains_too_long_lines(buf)
-}
-
-/// 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;
-        }
-
-        Ok(write_len)
-    }
-
-    fn flush(&mut self) -> io::Result<()> {
-        self.writer.flush()
-    }
-}
-
 /// In place conversion to CRLF line endings
 fn in_place_crlf_line_endings(string: &mut String) {
     let indices = find_all_lf_char_indices(string);
@@ -377,6 +285,8 @@ fn find_all_lf_char_indices(s: &str) -> Vec<usize> {
 
 #[cfg(test)]
 mod test {
+    use pretty_assertions::assert_eq;
+
     use super::{in_place_crlf_line_endings, Body, ContentTransferEncoding};
 
     #[test]
@@ -509,13 +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!(
+        assert_eq!(encoded.as_ref(), b"Questo messaggio =C3=A8 corto");
-            encoded.as_ref(),
-            b"=D0=9F=D1=80=D0=B8=D0=B2=D0=B5=D1=82, =D0=BC=D0=B8=D1=80!".as_ref()
-        );
     }
 
     #[test]
@@ -547,14 +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",
+                "Se lo standard =F0=9F=93=AC fosse stato pi=C3=B9 semplice avremmo finito mo=\r\n",
-                "=D1=83=D0=BD=D0=B8=D0=BA=D0=BE=D0=B4=D0=B5"
+                "lto prima."
             )
             .as_bytes()
         );
@@ -562,27 +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(
+        let encoded =
-            vec![0, 1, 2, 3, 4, 5, 6, 7, 8, 9],
+            Body::new_with_encoding(vec![0; 80], ContentTransferEncoding::Base64).unwrap();
-            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();

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

@@ -3,7 +3,7 @@ use std::{
     str::FromStr,
 };
 
-use super::{Header, HeaderName};
+use super::{Header, HeaderName, HeaderValue};
 use crate::BoxError;
 
 /// `Content-Transfer-Encoding` of the body
@@ -13,12 +13,14 @@ use crate::BoxError;
 /// use-caches this header shouldn't be set manually.
 #[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,
     /// Requires `8BITMIME`
     EightBit,
@@ -35,8 +37,9 @@ impl Header for ContentTransferEncoding {
         Ok(s.parse()?)
     }
 
-    fn display(&self) -> String {
+    fn display(&self) -> HeaderValue {
-        self.to_string()
+        let val = self.to_string();
+        HeaderValue::dangerous_new_pre_encoded(Self::name(), val.clone(), val)
     }
 }
 
@@ -66,16 +69,12 @@ impl FromStr for ContentTransferEncoding {
     }
 }
 
-impl Default for ContentTransferEncoding {
-    fn default() -> Self {
-        ContentTransferEncoding::Base64
-    }
-}
-
 #[cfg(test)]
 mod test {
+    use pretty_assertions::assert_eq;
+
     use super::ContentTransferEncoding;
-    use crate::message::header::{HeaderName, Headers};
+    use crate::message::header::{HeaderName, HeaderValue, Headers};
 
     #[test]
     fn format_content_transfer_encoding() {
@@ -94,20 +93,20 @@ mod test {
     fn parse_content_transfer_encoding() {
         let mut headers = Headers::new();
 
-        headers.insert_raw(
+        headers.insert_raw(HeaderValue::new(
             HeaderName::new_from_ascii_str("Content-Transfer-Encoding"),
-            "7bit".to_string(),
+            "7bit".to_owned(),
-        );
+        ));
 
         assert_eq!(
             headers.get::<ContentTransferEncoding>(),
             Some(ContentTransferEncoding::SevenBit)
         );
 
-        headers.insert_raw(
+        headers.insert_raw(HeaderValue::new(
             HeaderName::new_from_ascii_str("Content-Transfer-Encoding"),
-            "base64".to_string(),
+            "base64".to_owned(),
-        );
+        ));
 
         assert_eq!(
             headers.get::<ContentTransferEncoding>(),

src/message/header/content_disposition.rs

@@ -1,29 +1,57 @@
-use super::{Header, HeaderName};
+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(String);
+pub struct ContentDisposition(HeaderValue);
 
 impl ContentDisposition {
     /// An attachment which should be displayed inline into the message
     pub fn inline() -> Self {
-        Self("inline".into())
+        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 were to be downloaded
+    /// species the filename in case it is downloaded
     pub fn inline_with_name(file_name: &str) -> Self {
-        debug_assert!(!file_name.contains('"'), "file_name shouldn't contain '\"'");
+        Self::with_name("inline", file_name)
-        Self(format!("inline; filename=\"{}\"", 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 {
-        debug_assert!(!file_name.contains('"'), "file_name shouldn't contain '\"'");
+        Self::with_name("attachment", file_name)
-        Self(format!("attachment; filename=\"{}\"", 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,
+        ))
     }
 }
 
@@ -33,18 +61,28 @@ impl Header for ContentDisposition {
     }
 
     fn parse(s: &str) -> Result<Self, BoxError> {
-        Ok(Self(s.into()))
+        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) -> String {
+    fn display(&self) -> HeaderValue {
         self.0.clone()
     }
 }
 
 #[cfg(test)]
 mod test {
+    use pretty_assertions::assert_eq;
+
     use super::ContentDisposition;
-    use crate::message::header::{HeaderName, Headers};
+    use crate::message::header::{HeaderName, HeaderValue, Headers};
 
     #[test]
     fn format_content_disposition() {
@@ -52,12 +90,12 @@ mod test {
 
         headers.set(ContentDisposition::inline());
 
-        assert_eq!(format!("{}", headers), "Content-Disposition: inline\r\n");
+        assert_eq!(format!("{headers}"), "Content-Disposition: inline\r\n");
 
         headers.set(ContentDisposition::attachment("something.txt"));
 
         assert_eq!(
-            format!("{}", headers),
+            format!("{headers}"),
             "Content-Disposition: attachment; filename=\"something.txt\"\r\n"
         );
     }
@@ -66,20 +104,20 @@ mod test {
     fn parse_content_disposition() {
         let mut headers = Headers::new();
 
-        headers.insert_raw(
+        headers.insert_raw(HeaderValue::new(
             HeaderName::new_from_ascii_str("Content-Disposition"),
-            "inline".to_string(),
+            "inline".to_owned(),
-        );
+        ));
 
         assert_eq!(
             headers.get::<ContentDisposition>(),
             Some(ContentDisposition::inline())
         );
 
-        headers.insert_raw(
+        headers.insert_raw(HeaderValue::new(
             HeaderName::new_from_ascii_str("Content-Disposition"),
-            "attachment; filename=\"something.txt\"".to_string(),
+            "attachment; filename=\"something.txt\"".to_owned(),
-        );
+        ));
 
         assert_eq!(
             headers.get::<ContentDisposition>(),

src/message/header/content_type.rs

@@ -6,17 +6,17 @@ use std::{
 
 use mime::Mime;
 
-use super::{Header, HeaderName};
+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
+/// 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
+/// [MIME type]: https://www.iana.org/assignments/media-types/media-types.xhtml
 #[derive(Debug, Clone, PartialEq, Eq)]
 pub struct ContentType(Mime);
 
@@ -54,8 +54,8 @@ impl Header for ContentType {
         Ok(Self(s.parse()?))
     }
 
-    fn display(&self) -> String {
+    fn display(&self) -> HeaderValue {
-        self.0.to_string()
+        HeaderValue::new(Self::name(), self.0.to_string())
     }
 }
 
@@ -94,11 +94,13 @@ impl Display for ContentTypeErr {
 // -- Serialization and Deserialization --
 #[cfg(feature = "serde")]
 mod serde {
-    use serde::de::{self, Deserialize, Deserializer, Visitor};
-    use serde::ser::{Serialize, Serializer};
-
     use std::fmt;
 
+    use serde::{
+        de::{self, Deserialize, Deserializer, Visitor},
+        ser::{Serialize, Serializer},
+    };
+
     use super::ContentType;
 
     impl Serialize for ContentType {
@@ -117,7 +119,7 @@ mod serde {
         {
             struct ContentTypeVisitor;
 
-            impl<'de> Visitor<'de> for ContentTypeVisitor {
+            impl Visitor<'_> for ContentTypeVisitor {
                 type Value = ContentType;
 
                 // The error message which states what the Visitor expects to
@@ -133,8 +135,7 @@ mod serde {
                     match ContentType::parse(mime) {
                         Ok(content_type) => Ok(content_type),
                         Err(_) => Err(E::custom(format!(
-                            "Couldn't parse the following MIME-Type: {}",
+                            "Couldn't parse the following MIME-Type: {mime}"
-                            mime
                         ))),
                     }
                 }
@@ -147,8 +148,10 @@ mod serde {
 
 #[cfg(test)]
 mod test {
+    use pretty_assertions::assert_eq;
+
     use super::ContentType;
-    use crate::message::header::{HeaderName, Headers};
+    use crate::message::header::{HeaderName, HeaderValue, Headers};
 
     #[test]
     fn format_content_type() {
@@ -173,17 +176,17 @@ mod test {
     fn parse_content_type() {
         let mut headers = Headers::new();
 
-        headers.insert_raw(
+        headers.insert_raw(HeaderValue::new(
             HeaderName::new_from_ascii_str("Content-Type"),
-            "text/plain; charset=utf-8".to_string(),
+            "text/plain; charset=utf-8".to_owned(),
-        );
+        ));
 
         assert_eq!(headers.get::<ContentType>(), Some(ContentType::TEXT_PLAIN));
 
-        headers.insert_raw(
+        headers.insert_raw(HeaderValue::new(
             HeaderName::new_from_ascii_str("Content-Type"),
-            "text/html; charset=utf-8".to_string(),
+            "text/html; charset=utf-8".to_owned(),
-        );
+        ));
 
         assert_eq!(headers.get::<ContentType>(), Some(ContentType::TEXT_HTML));
     }

src/message/header/date.rs

@@ -2,13 +2,13 @@ use std::time::SystemTime;
 
 use httpdate::HttpDate;
 
-use super::{Header, HeaderName};
+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)]
+#[derive(Debug, Clone, Copy, PartialEq, Eq)]
 pub struct Date(HttpDate);
 
 impl Date {
@@ -21,7 +21,7 @@ impl Date {
     ///
     /// Shortcut for `Date::new(SystemTime::now())`
     pub fn now() -> Self {
-        Self::new(SystemTime::now())
+        Self::new(crate::time::now())
     }
 }
 
@@ -32,29 +32,29 @@ impl Header for Date {
 
     fn parse(s: &str) -> Result<Self, BoxError> {
         let mut s = String::from(s);
-        if s.ends_with(" -0000") {
+        if s.ends_with("+0000") {
             // The httpdate crate expects the `Date` to end in ` GMT`, but email
-            // uses `-0000`, so we crudely fix this issue here.
+            // uses `+0000` to indicate UTC, so we crudely fix this issue here.
 
-            s.truncate(s.len() - "-0000".len());
+            s.truncate(s.len() - "+0000".len());
             s.push_str("GMT");
         }
 
         Ok(Self(s.parse::<HttpDate>()?))
     }
 
-    fn display(&self) -> String {
+    fn display(&self) -> HeaderValue {
-        let mut s = self.0.to_string();
+        let mut val = self.0.to_string();
-        if s.ends_with(" GMT") {
+        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`
+            // so we replace `GMT` with `+0000`
-            s.truncate(s.len() - "GMT".len());
+            val.truncate(val.len() - "GMT".len());
-            s.push_str("-0000");
+            val.push_str("+0000");
         }
 
-        s
+        HeaderValue::dangerous_new_pre_encoded(Self::name(), val.clone(), val)
     }
 }
 
@@ -74,8 +74,10 @@ impl From<Date> for SystemTime {
 mod test {
     use std::time::{Duration, SystemTime};
 
+    use pretty_assertions::assert_eq;
+
     use super::Date;
-    use crate::message::header::{HeaderName, Headers};
+    use crate::message::header::{HeaderName, HeaderValue, Headers};
 
     #[test]
     fn format_date() {
@@ -88,7 +90,7 @@ mod test {
 
         assert_eq!(
             headers.to_string(),
-            "Date: Tue, 15 Nov 1994 08:12:31 -0000\r\n".to_string()
+            "Date: Tue, 15 Nov 1994 08:12:31 +0000\r\n".to_owned()
         );
 
         // Tue, 15 Nov 1994 08:12:32 GMT
@@ -98,7 +100,7 @@ mod test {
 
         assert_eq!(
             headers.to_string(),
-            "Date: Tue, 15 Nov 1994 08:12:32 -0000\r\n"
+            "Date: Tue, 15 Nov 1994 08:12:32 +0000\r\n"
         );
     }
 
@@ -106,10 +108,10 @@ mod test {
     fn parse_date() {
         let mut headers = Headers::new();
 
-        headers.insert_raw(
+        headers.insert_raw(HeaderValue::new(
             HeaderName::new_from_ascii_str("Date"),
-            "Tue, 15 Nov 1994 08:12:31 -0000".to_string(),
+            "Tue, 15 Nov 1994 08:12:31 +0000".to_owned(),
-        );
+        ));
 
         assert_eq!(
             headers.get::<Date>(),
@@ -118,10 +120,10 @@ mod test {
             ))
         );
 
-        headers.insert_raw(
+        headers.insert_raw(HeaderValue::new(
             HeaderName::new_from_ascii_str("Date"),
-            "Tue, 15 Nov 1994 08:12:32 -0000".to_string(),
+            "Tue, 15 Nov 1994 08:12:32 +0000".to_owned(),
-        );
+        ));
 
         assert_eq!(
             headers.get::<Date>(),

src/message/header/mailbox.rs

@@ -1,4 +1,6 @@
-use super::{Header, HeaderName};
+use email_encoding::headers::writer::EmailWriter;
+
+use super::{Header, HeaderName, HeaderValue};
 use crate::{
     message::mailbox::{Mailbox, Mailboxes},
     BoxError,
@@ -12,7 +14,7 @@ pub trait MailboxesHeader {
 macro_rules! mailbox_header {
     ($(#[$doc:meta])*($type_name: ident, $header_name: expr)) => {
         $(#[$doc])*
-        #[derive(Debug, Clone, PartialEq)]
+        #[derive(Debug, Clone, PartialEq, Eq)]
         pub struct $type_name(Mailbox);
 
         impl Header for $type_name {
@@ -25,8 +27,15 @@ macro_rules! mailbox_header {
                 Ok(Self(mailbox))
             }
 
-            fn display(&self) -> String {
+            fn display(&self) -> HeaderValue {
-                self.0.to_string()
+                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)
             }
         }
 
@@ -49,7 +58,7 @@ macro_rules! mailbox_header {
 macro_rules! mailboxes_header {
     ($(#[$doc:meta])*($type_name: ident, $header_name: expr)) => {
         $(#[$doc])*
-        #[derive(Debug, Clone, PartialEq)]
+        #[derive(Debug, Clone, PartialEq, Eq)]
         pub struct $type_name(pub(crate) Mailboxes);
 
         impl MailboxesHeader for $type_name {
@@ -68,8 +77,15 @@ macro_rules! mailboxes_header {
                 Ok(Self(mailbox))
             }
 
-            fn display(&self) -> String {
+            fn display(&self) -> HeaderValue {
-                self.0.to_string()
+                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)
             }
         }
 
@@ -94,7 +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())
@@ -108,7 +124,7 @@ mailboxes_header! {
 
     `From` header
 
-    This header contains [`Mailboxes`][self::Mailboxes].
+    This header contains [`Mailboxes`].
 
      */
     (From, "From")
@@ -119,7 +135,7 @@ mailboxes_header! {
 
     `Reply-To` header
 
-    This header contains [`Mailboxes`][self::Mailboxes].
+    This header contains [`Mailboxes`].
 
      */
     (ReplyTo, "Reply-To")
@@ -130,7 +146,7 @@ mailboxes_header! {
 
     `To` header
 
-    This header contains [`Mailboxes`][self::Mailboxes].
+    This header contains [`Mailboxes`].
 
      */
     (To, "To")
@@ -141,7 +157,7 @@ mailboxes_header! {
 
     `Cc` header
 
-    This header contains [`Mailboxes`][self::Mailboxes].
+    This header contains [`Mailboxes`].
 
      */
     (Cc, "Cc")
@@ -152,7 +168,7 @@ mailboxes_header! {
 
     `Bcc` header
 
-    This header contains [`Mailboxes`][self::Mailboxes].
+    This header contains [`Mailboxes`].
 
      */
     (Bcc, "Bcc")
@@ -160,8 +176,10 @@ mailboxes_header! {
 
 #[cfg(test)]
 mod test {
+    use pretty_assertions::assert_eq;
+
     use super::{From, Mailbox, Mailboxes};
-    use crate::message::header::{HeaderName, Headers};
+    use crate::message::header::{HeaderName, HeaderValue, Headers};
 
     #[test]
     fn format_single_without_name() {
@@ -175,12 +193,12 @@ mod test {
 
     #[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!(headers.to_string(), "From: K. <kayo@example.com>\r\n");
+        assert_eq!(headers.to_string(), "From: Kayo <kayo@example.com>\r\n");
     }
 
     #[test]
@@ -201,7 +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(),
         ];
 
@@ -210,7 +228,7 @@ mod test {
 
         assert_eq!(
             headers.to_string(),
-            "From: K. <kayo@example.com>, Pony P. <pony@domain.tld>\r\n"
+            "From: Kayo <kayo@example.com>, \"Pony P.\" <pony@domain.tld>\r\n"
         );
     }
 
@@ -232,10 +250,10 @@ mod test {
         let from = vec!["kayo@example.com".parse().unwrap()].into();
 
         let mut headers = Headers::new();
-        headers.insert_raw(
+        headers.insert_raw(HeaderValue::new(
             HeaderName::new_from_ascii_str("From"),
-            "kayo@example.com".to_string(),
+            "kayo@example.com".to_owned(),
-        );
+        ));
 
         assert_eq!(headers.get::<From>(), Some(From(from)));
     }
@@ -245,10 +263,10 @@ mod test {
         let from = vec!["K. <kayo@example.com>".parse().unwrap()].into();
 
         let mut headers = Headers::new();
-        headers.insert_raw(
+        headers.insert_raw(HeaderValue::new(
             HeaderName::new_from_ascii_str("From"),
-            "K. <kayo@example.com>".to_string(),
+            "K. <kayo@example.com>".to_owned(),
-        );
+        ));
 
         assert_eq!(headers.get::<From>(), Some(From(from)));
     }
@@ -261,10 +279,10 @@ mod test {
         ];
 
         let mut headers = Headers::new();
-        headers.insert_raw(
+        headers.insert_raw(HeaderValue::new(
             HeaderName::new_from_ascii_str("From"),
-            "kayo@example.com, pony@domain.tld".to_string(),
+            "kayo@example.com, pony@domain.tld".to_owned(),
-        );
+        ));
 
         assert_eq!(headers.get::<From>(), Some(From(from.into())));
     }
@@ -277,11 +295,65 @@ mod test {
         ];
 
         let mut headers = Headers::new();
-        headers.insert_raw(
+        headers.insert_raw(HeaderValue::new(
             HeaderName::new_from_ascii_str("From"),
-            "K. <kayo@example.com>, Pony P. <pony@domain.tld>".to_string(),
+            "K. <kayo@example.com>, Pony P. <pony@domain.tld>".to_owned(),
-        );
+        ));
 
         assert_eq!(headers.get::<From>(), Some(From(from.into())));
     }
+
+    #[test]
+    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.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_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

@@ -3,10 +3,12 @@
 use std::{
     borrow::Cow,
     error::Error,
-    fmt::{self, Display, Formatter},
+    fmt::{self, Display, Formatter, Write},
     ops::Deref,
 };
 
+use email_encoding::headers::writer::EmailWriter;
+
 pub use self::{
     content::*,
     content_disposition::ContentDisposition,
@@ -34,13 +36,13 @@ pub trait Header: Clone {
 
     fn parse(s: &str) -> Result<Self, BoxError>;
 
-    fn display(&self) -> String;
+    fn display(&self) -> HeaderValue;
 }
 
 /// A set of email headers
 #[derive(Debug, Clone, Default)]
 pub struct Headers {
-    headers: Vec<(HeaderName, String)>,
+    headers: Vec<HeaderValue>,
 }
 
 impl Headers {
@@ -64,17 +66,18 @@ impl Headers {
         }
     }
 
-    /// Returns a copy of an `Header` present in `Headers`
+    /// 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| H::parse(raw).ok())
+        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(H::name(), header.display());
+        self.insert_raw(header.display());
     }
 
     /// Remove `Header` from `Headers`, returning it
@@ -82,7 +85,7 @@ impl Headers {
     /// Returns `None` if `Header` isn't in `Headers`.
     pub fn remove<H: Header>(&mut self) -> Option<H> {
         self.remove_raw(&H::name())
-            .and_then(|(_name, raw)| H::parse(&raw).ok())
+            .and_then(|value| H::parse(&value.raw_value).ok())
     }
 
     /// Clears `Headers`, removing all headers from it
@@ -97,62 +100,42 @@ impl Headers {
     ///
     /// Returns `None` if `name` isn't present in `Headers`.
     pub fn get_raw(&self, name: &str) -> Option<&str> {
-        self.find_header(name).map(|(_name, value)| value)
+        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, name: HeaderName, value: String) {
+    pub fn insert_raw(&mut self, value: HeaderValue) {
-        match self.find_header_mut(&name) {
+        match self.find_header_mut(&value.name) {
-            Some((_, current_value)) => {
+            Some(current_value) => {
                 *current_value = value;
             }
             None => {
-                self.headers.push((name, value));
+                self.headers.push(value);
             }
         }
     }
 
-    /// Appends a raw header into `Headers`
-    ///
-    /// If a header with a name of `name` is already present,
-    /// appends `, ` + `value` to it's current value.
-    pub fn append_raw(&mut self, name: HeaderName, value: String) {
-        match self.find_header_mut(&name) {
-            Some((_name, prev_value)) => {
-                prev_value.push_str(", ");
-                prev_value.push_str(&value);
-            }
-            None => self.headers.push((name, 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<(HeaderName, String)> {
+    pub fn remove_raw(&mut self, name: &str) -> Option<HeaderValue> {
         self.find_header_index(name).map(|i| self.headers.remove(i))
     }
 
-    fn find_header(&self, name: &str) -> Option<(&HeaderName, &str)> {
+    pub(crate) fn find_header(&self, name: &str) -> Option<&HeaderValue> {
-        self.headers
+        self.headers.iter().find(|value| name == value.name)
-            .iter()
-            .find(|&(name_, _value)| name.eq_ignore_ascii_case(name_))
-            .map(|t| (&t.0, t.1.as_str()))
     }
 
-    fn find_header_mut(&mut self, name: &str) -> Option<(&HeaderName, &mut String)> {
+    fn find_header_mut(&mut self, name: &str) -> Option<&mut HeaderValue> {
-        self.headers
+        self.headers.iter_mut().find(|value| name == value.name)
-            .iter_mut()
-            .find(|(name_, _value)| name.eq_ignore_ascii_case(name_))
-            .map(|t| (&t.0, &mut t.1))
     }
 
     fn find_header_index(&self, name: &str) -> Option<usize> {
         self.headers
             .iter()
             .enumerate()
-            .find(|&(_i, (name_, _value))| name.eq_ignore_ascii_case(name_))
+            .find(|(_i, value)| name == value.name)
             .map(|(i, _)| i)
     }
 }
@@ -160,10 +143,10 @@ impl Headers {
 impl Display for Headers {
     /// Formats `Headers`, ready to put them into an email
     fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
-        for (name, value) in &self.headers {
+        for value in &self.headers {
-            Display::fmt(name, f)?;
+            f.write_str(&value.name)?;
             f.write_str(": ")?;
-            HeaderValueEncoder::encode(name, value, f)?;
+            f.write_str(&value.encoded_value)?;
             f.write_str("\r\n")?;
         }
 
@@ -174,18 +157,9 @@ impl Display for Headers {
 /// A possible error when converting a `HeaderName` from another type.
 // comes from `http` crate
 #[allow(missing_copy_implementations)]
-#[derive(Clone)]
+#[derive(Debug, Clone)]
-pub struct InvalidHeaderName {
+#[non_exhaustive]
-    _priv: (),
+pub struct InvalidHeaderName;
-}
-
-impl fmt::Debug for InvalidHeaderName {
-    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
-        f.debug_struct("InvalidHeaderName")
-            // skip _priv noise
-            .finish()
-    }
-}
 
 impl fmt::Display for InvalidHeaderName {
     fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
@@ -202,14 +176,11 @@ 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()
+        if !ascii.is_empty() && ascii.len() <= 76 && ascii.is_ascii() && !ascii.contains([':', ' '])
-            && ascii.len() <= 76
-            && ascii.is_ascii()
-            && !ascii.contains(|c| c == ':' || c == ' ')
         {
             Ok(Self(Cow::Owned(ascii)))
         } else {
-            Err(InvalidHeaderName { _priv: () })
+            Err(InvalidHeaderName)
         }
     }
 
@@ -270,75 +241,102 @@ impl AsRef<str> for HeaderName {
 
 impl PartialEq<HeaderName> for HeaderName {
     fn eq(&self, other: &HeaderName) -> bool {
-        let s1: &str = self.as_ref();
+        self.eq_ignore_ascii_case(other)
-        let s2: &str = other.as_ref();
-        s1 == s2
     }
 }
 
 impl PartialEq<&str> for HeaderName {
     fn eq(&self, other: &&str) -> bool {
-        let s: &str = self.as_ref();
+        self.eq_ignore_ascii_case(other)
-        s == *other
     }
 }
 
 impl PartialEq<HeaderName> for &str {
     fn eq(&self, other: &HeaderName) -> bool {
-        let s: &str = other.as_ref();
+        self.eq_ignore_ascii_case(other)
-        *self == s
     }
 }
 
-const ENCODING_START_PREFIX: &str = "=?utf-8?b?";
+/// A safe for use header value
-const ENCODING_END_SUFFIX: &str = "?=";
+#[derive(Debug, Clone, PartialEq)]
-const MAX_LINE_LEN: usize = 76;
+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 {
+struct HeaderValueEncoder<'a> {
-    line_len: usize,
+    writer: EmailWriter<'a>,
     encode_buf: String,
 }
 
-impl HeaderValueEncoder {
+impl<'a> HeaderValueEncoder<'a> {
-    fn encode(name: &str, value: &str, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+    fn encode(name: &str, value: &'a str, f: &'a mut impl fmt::Write) -> fmt::Result {
-        let (words_iter, encoder) = Self::new(name, value);
+        let encoder = Self::new(name, f);
-        encoder.format(words_iter, f)
+        encoder.format(value.split_inclusive(' '))
     }
 
-    fn new<'a>(name: &str, value: &'a str) -> (WordsPlusFillIterator<'a>, Self) {
+    fn new(name: &str, writer: &'a mut dyn Write) -> Self {
-        (
+        let line_len = name.len() + ": ".len();
-            WordsPlusFillIterator { s: value },
+        let writer = EmailWriter::new(writer, line_len, 0, false);
+
         Self {
-                line_len: name.len() + ": ".len(),
+            writer,
             encode_buf: String::new(),
-            },
+        }
-        )
-    }
-
-    fn format(
-        mut self,
-        words_iter: WordsPlusFillIterator<'_>,
-        f: &mut fmt::Formatter<'_>,
-    ) -> fmt::Result {
-        /// Estimate if an encoded string of `len` would fix in an empty line
-        fn would_fit_new_line(len: usize) -> bool {
-            len < (MAX_LINE_LEN - " ".len())
-        }
-
-        /// Estimate how long a string of `len` would be after base64 encoding plus
-        /// adding the encoding prefix and suffix to it
-        fn base64_len(len: usize) -> usize {
-            ENCODING_START_PREFIX.len() + (len * 4 / 3 + 4) + ENCODING_END_SUFFIX.len()
-        }
-
-        /// Estimate how many more bytes we can fit in the current line
-        fn available_len_to_max_encode_len(len: usize) -> usize {
-            len.saturating_sub(
-                ENCODING_START_PREFIX.len() + (len * 3 / 4 + 4) + ENCODING_END_SUFFIX.len(),
-            )
     }
 
+    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);
 
@@ -346,207 +344,54 @@ impl HeaderValueEncoder {
                 // This word only contains allowed characters
 
                 // the next word is allowed, but we may have accumulated some words to encode
-                self.flush_encode_buf(f, true)?;
+                self.flush_encode_buf()?;
 
-                if next_word.len() > self.remaining_line_len() {
+                self.writer.folding().write_str(next_word)?;
-                    // not enough space left on this line to encode word
-
-                    if self.something_written_to_this_line() && would_fit_new_line(next_word.len())
-                    {
-                        // word doesn't fit this line, but something had already been written to it,
-                        // and word would fit the next line, so go to a new line
-                        // so go to new line
-                        self.new_line(f)?;
-                    } else {
-                        // word neither fits this line and the next one, cut it
-                        // in the middle and make it fit
-
-                        let mut next_word = next_word;
-
-                        while !next_word.is_empty() {
-                            if self.remaining_line_len() == 0 {
-                                self.new_line(f)?;
-                            }
-
-                            let len = self.remaining_line_len().min(next_word.len());
-                            let first_part = &next_word[..len];
-                            next_word = &next_word[len..];
-
-                            f.write_str(first_part)?;
-                            self.line_len += first_part.len();
-                        }
-
-                        continue;
-                    }
-                }
-
-                // word fits, write it!
-                f.write_str(next_word)?;
-                self.line_len += next_word.len();
             } else {
                 // This word contains unallowed characters
-
-                if self.remaining_line_len() >= base64_len(self.encode_buf.len() + next_word.len())
-                {
-                    // next_word fits
                 self.encode_buf.push_str(next_word);
-                    continue;
-                }
-
-                // next_word doesn't fit this line
-
-                if would_fit_new_line(base64_len(next_word.len())) {
-                    // ...but it would fit the next one
-
-                    self.flush_encode_buf(f, false)?;
-                    self.new_line(f)?;
-
-                    self.encode_buf.push_str(next_word);
-                    continue;
-                }
-
-                // ...and also wouldn't fit the next one.
-                // chop it up into pieces
-
-                let mut next_word = next_word;
-
-                while !next_word.is_empty() {
-                    let mut len = available_len_to_max_encode_len(self.remaining_line_len())
-                        .min(next_word.len());
-
-                    if len == 0 {
-                        self.flush_encode_buf(f, false)?;
-                        self.new_line(f)?;
-                    }
-
-                    // avoid slicing on a char boundary
-                    while !next_word.is_char_boundary(len) {
-                        len += 1;
-                    }
-                    let first_part = &next_word[..len];
-                    next_word = &next_word[len..];
-
-                    self.encode_buf.push_str(first_part);
-                }
             }
         }
 
-        self.flush_encode_buf(f, false)?;
+        self.flush_encode_buf()?;
 
         Ok(())
     }
 
-    /// Returns the number of bytes left for the current line
+    fn flush_encode_buf(&mut self) -> fmt::Result {
-    fn remaining_line_len(&self) -> usize {
-        MAX_LINE_LEN - self.line_len
-    }
-
-    /// Returns true if something has been written to the current line
-    fn something_written_to_this_line(&self) -> bool {
-        self.line_len > 1
-    }
-
-    fn flush_encode_buf(
-        &mut self,
-        f: &mut fmt::Formatter<'_>,
-        switching_to_allowed: bool,
-    ) -> fmt::Result {
-        use std::fmt::Write;
-
         if self.encode_buf.is_empty() {
             // nothing to encode
             return Ok(());
         }
 
-        let mut write_after = None;
+        let prefix = self.encode_buf.trim_end_matches(' ');
+        email_encoding::headers::rfc2047::encode(prefix, &mut self.writer)?;
 
-        if switching_to_allowed {
+        // TODO: add a better API for doing this in email-encoding
-            // If the next word only contains allowed characters, and the string to encode
+        let spaces = self.encode_buf.len() - prefix.len();
-            // ends with a space, take the space out of the part to encode
+        for _ in 0..spaces {
-
+            self.writer.space();
-            let last_char = self.encode_buf.pop().expect("self.encode_buf isn't empty");
-            if is_space_like(last_char) {
-                write_after = Some(last_char);
-            } else {
-                self.encode_buf.push(last_char);
-            }
-        }
-
-        f.write_str(ENCODING_START_PREFIX)?;
-        let encoded = base64::display::Base64Display::with_config(
-            self.encode_buf.as_bytes(),
-            base64::STANDARD,
-        );
-        Display::fmt(&encoded, f)?;
-        f.write_str(ENCODING_END_SUFFIX)?;
-
-        self.line_len += ENCODING_START_PREFIX.len();
-        self.line_len += self.encode_buf.len() * 4 / 3 + 4;
-        self.line_len += ENCODING_END_SUFFIX.len();
-
-        if let Some(write_after) = write_after {
-            f.write_char(write_after)?;
-            self.line_len += 1;
         }
 
         self.encode_buf.clear();
         Ok(())
     }
-
-    fn new_line(&mut self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
-        f.write_str("\r\n ")?;
-        self.line_len = 1;
-
-        Ok(())
-    }
-}
-
-/// Iterator yielding a string split space by space, but including all space
-/// characters between it and the next word
-struct WordsPlusFillIterator<'a> {
-    s: &'a str,
-}
-
-impl<'a> Iterator for WordsPlusFillIterator<'a> {
-    type Item = &'a str;
-
-    fn next(&mut self) -> Option<Self::Item> {
-        if self.s.is_empty() {
-            return None;
-        }
-
-        let next_word = self
-            .s
-            .char_indices()
-            .skip(1)
-            .skip_while(|&(_i, c)| !is_space_like(c))
-            .find(|&(_i, c)| !is_space_like(c))
-            .map(|(i, _)| i);
-
-        let word = &self.s[..next_word.unwrap_or_else(|| self.s.len())];
-        self.s = &self.s[word.len()..];
-        Some(word)
-    }
-}
-
-const fn is_space_like(c: char) -> bool {
-    c == ',' || c == ' '
 }
 
 fn allowed_str(s: &str) -> bool {
-    s.chars().all(allowed_char)
+    s.bytes().all(allowed_char)
 }
 
-const fn allowed_char(c: char) -> bool {
+const fn allowed_char(c: u8) -> bool {
-    c >= 1 as char && c <= 9 as char
+    c >= 1 && c <= 9 || c == 11 || c == 12 || c >= 14 && c <= 127
-        || c == 11 as char
-        || c == 12 as char
-        || c >= 14 as char && c <= 127 as char
 }
 
 #[cfg(test)]
 mod tests {
-    use super::{HeaderName, Headers};
+    use pretty_assertions::assert_eq;
+
+    use super::{HeaderName, HeaderValue, Headers, To};
+    use crate::message::Mailboxes;
 
     #[test]
     fn valid_headername() {
@@ -570,7 +415,7 @@ mod tests {
 
     #[test]
     fn empty_headername() {
-        assert!(HeaderName::new_from_ascii(String::from("")).is_err());
+        assert!(HeaderName::new_from_ascii("".to_owned()).is_err());
     }
 
     #[test]
@@ -602,15 +447,69 @@ mod tests {
         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(
+        headers.insert_raw(HeaderValue::new(
             HeaderName::new_from_ascii_str("To"),
-            "John Doe <example@example.com>, Jean Dupont <jean@example.com>".to_string(),
+            "John Doe <example@example.com>, Jean Dupont <jean@example.com>".to_owned(),
-        );
+        ));
 
         assert_eq!(
             headers.to_string(),
@@ -621,16 +520,16 @@ mod tests {
     #[test]
     fn format_ascii_with_folding() {
         let mut headers = Headers::new();
-        headers.insert_raw(
+        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_string(),
+            "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",
+                "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",
+                " <johnsmith@example.com>, Pinco Pallino <pincopallino@example.com>, Jemand\r\n",
                 " <jemand@example.com>, Jean Dupont <jean@example.com>\r\n"
             )
         );
@@ -639,16 +538,16 @@ mod tests {
     #[test]
     fn format_ascii_with_folding_long_line() {
         let mut headers = Headers::new();
-        headers.insert_raw(
+        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_string()
+            "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 ",
+                "Subject: Hello! This is lettre, and this\r\n",
-                "IsAVeryLongLineDoYouKnowWhatsGoingToHappenIGuessWeAreGoingToFindOut. Ok I \r\n",
+                " IsAVeryLongLineDoYouKnowWhatsGoingToHappenIGuessWeAreGoingToFindOut. Ok I\r\n",
                 " guess that's it!\r\n"
             )
         );
@@ -658,15 +557,17 @@ mod tests {
     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_string()
+            "Hello! IGuessTheLastLineWasntLongEnoughSoLetsTryAgainShallWeWhatDoYouThinkItsGoingToHappenIGuessWereAboutToFindOut! I don't know".to_owned()
-        );
+        ));
 
         assert_eq!(
             headers.to_string(),
             concat!(
-                "Subject: Hello! IGuessTheLastLineWasntLongEnoughSoLetsTryAgainShallWeWhatDoY\r\n",
+                "Subject: Hello!\r\n",
-                " ouThinkItsGoingToHappenIGuessWereAboutToFindOut! I don't know\r\n",
+                " IGuessTheLastLineWasntLongEnoughSoLetsTryAgainShallWeWhatDoYouThinkItsGoingToHappenIGuessWereAboutToFindOut!\r\n",
+                " I don't know\r\n",
             )
         );
     }
@@ -674,28 +575,24 @@ mod tests {
     #[test]
     fn format_ascii_with_folding_giant_word() {
         let mut headers = Headers::new();
-        headers.insert_raw(
+        headers.insert_raw(HeaderValue::new(
             HeaderName::new_from_ascii_str("Subject"),
-            "1abcdefghijklmnopqrstuvwxyz2abcdefghijklmnopqrstuvwxyz3abcdefghijklmnopqrstuvwxyz4abcdefghijklmnopqrstuvwxyz5abcdefghijklmnopqrstuvwxyz6abcdefghijklmnopqrstuvwxyz".to_string()
+            "1abcdefghijklmnopqrstuvwxyz2abcdefghijklmnopqrstuvwxyz3abcdefghijklmnopqrstuvwxyz4abcdefghijklmnopqrstuvwxyz5abcdefghijklmnopqrstuvwxyz6abcdefghijklmnopqrstuvwxyz".to_owned()
-        );
+        ));
 
         assert_eq!(
             headers.to_string(),
-            concat!(
+            "Subject: 1abcdefghijklmnopqrstuvwxyz2abcdefghijklmnopqrstuvwxyz3abcdefghijklmnopqrstuvwxyz4abcdefghijklmnopqrstuvwxyz5abcdefghijklmnopqrstuvwxyz6abcdefghijklmnopqrstuvwxyz\r\n",
-                "Subject: 1abcdefghijklmnopqrstuvwxyz2abcdefghijklmnopqrstuvwxyz3abcdefghijkl\r\n",
-                " mnopqrstuvwxyz4abcdefghijklmnopqrstuvwxyz5abcdefghijklmnopqrstuvwxyz6abcdef\r\n",
-                " ghijklmnopqrstuvwxyz\r\n",
-            )
         );
     }
 
     #[test]
     fn format_special() {
         let mut headers = Headers::new();
-        headers.insert_raw(
+        headers.insert_raw(HeaderValue::new(
             HeaderName::new_from_ascii_str("To"),
-            "Seán <sean@example.com>".to_string(),
+            "Seán <sean@example.com>".to_owned(),
-        );
+        ));
 
         assert_eq!(
             headers.to_string(),
@@ -706,10 +603,10 @@ mod tests {
     #[test]
     fn format_special_emoji() {
         let mut headers = Headers::new();
-        headers.insert_raw(
+        headers.insert_raw(HeaderValue::new(
             HeaderName::new_from_ascii_str("To"),
-            "🌎 <world@example.com>".to_string(),
+            "🌎 <world@example.com>".to_owned(),
-        );
+        ));
 
         assert_eq!(
             headers.to_string(),
@@ -720,19 +617,43 @@ mod tests {
     #[test]
     fn format_special_with_folding() {
         let mut headers = Headers::new();
-        headers.insert_raw(
+        let to = To::from(Mailboxes::from_iter([
-            HeaderName::new_from_ascii_str("To"),
+            "🌍 <world@example.com>".parse().unwrap(),
-            "🌍 <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_string(),
+            "🦆 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+mhg==?= \r\n",
+                "To: =?utf-8?b?8J+MjQ==?= <world@example.com>, =?utf-8?b?8J+mhiBFdmVyeXdo?=\r\n",
-                " Everywhere <ducks@example.com>, =?utf-8?b?0JjQstCw0L3QvtCyIA==?=\r\n",
+                " =?utf-8?b?ZXJl?= <ducks@example.com>, =?utf-8?b?0JjQstCw0L3QvtCyINCY0LI=?=\r\n",
-                " =?utf-8?b?0JjQstCw0L0g0JjQstCw0L3QvtCy0LjRhw==?= <ivanov@example.com>, \r\n",
+                " =?utf-8?b?0LDQvSDQmNCy0LDQvdC+0LLQuNGH?= <ivanov@example.com>,\r\n",
-                " =?utf-8?b?SsSBbmlzIELEk3J6acWGxaE=?= <janis@example.com>, \r\n",
+                " =?utf-8?b?SsSBbmlzIELEk3J6acWGxaE=?= <janis@example.com>, =?utf-8?b?U2U=?=\r\n",
-                " =?utf-8?b?U2XDoW4gw5MgUnVkYcOt?= <sean@example.com>\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",
             )
         );
     }
@@ -741,23 +662,31 @@ mod tests {
     fn format_slice_on_char_boundary_bug() {
         let mut headers = Headers::new();
         headers.insert_raw(
+            HeaderValue::new(
             HeaderName::new_from_ascii_str("Subject"),
-            "🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳".to_string(),
+            "🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳🥳".to_owned(),)
         );
 
         assert_eq!(
             headers.to_string(),
-            "Subject: =?utf-8?b?8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz?=\r\n"
+            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(
+        headers.insert_raw(HeaderValue::new(
             HeaderName::new_from_ascii_str("Subject"),
-            "Hello! \r\n This is \" bad \0. 👋".to_string(),
+            "Hello! \r\n This is \" bad \0. 👋".to_owned(),
-        );
+        ));
 
         assert_eq!(
             headers.to_string(),
@@ -769,33 +698,37 @@ mod tests {
     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_string()
+            "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_string(),
+            "🌍 <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(
+        headers.insert_raw(HeaderValue::new(
             HeaderName::new_from_ascii_str("From"),
-            "Someone <somewhere@example.com>".to_string(),
+            "Someone <somewhere@example.com>".to_owned(),
-        );
+        ));
-        headers.insert_raw(
+        headers.insert_raw(HeaderValue::new(
             HeaderName::new_from_ascii_str("Content-Transfer-Encoding"),
-            "quoted-printable".to_string(),
+            "quoted-printable".to_owned(),
-        );
+        ));
 
         assert_eq!(
             headers.to_string(),
             concat!(
-                "Subject: Hello! This is lettre, and this \r\n",
+                "Subject: Hello! This is lettre, and this\r\n",
-                " IsAVeryLongLineDoYouKnowWhatsGoingToHappenIGuessWeAreGoingToFindOut. Ok I \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",
+                "To: =?utf-8?b?8J+MjQ==?= <world@example.com>, =?utf-8?b?8J+mhg==?=\r\n",
-                " Everywhere <ducks@example.com>, =?utf-8?b?0JjQstCw0L3QvtCyIA==?=\r\n",
+                " Everywhere <ducks@example.com>, =?utf-8?b?0JjQstCw0L3QvtCyINCY0LLQsNC9?=\r\n",
-                " =?utf-8?b?0JjQstCw0L0g0JjQstCw0L3QvtCy0LjRhw==?= <ivanov@example.com>, \r\n",
+                " =?utf-8?b?INCY0LLQsNC90L7QstC40Yc=?= <ivanov@example.com>,\r\n",
-                " =?utf-8?b?SsSBbmlzIELEk3J6acWGxaE=?= <janis@example.com>, \r\n",
+                " =?utf-8?b?SsSBbmlzIELEk3J6acWGxaE=?= <janis@example.com>, =?utf-8?b?U2U=?=\r\n",
-                " =?utf-8?b?U2XDoW4gw5MgUnVkYcOt?= <sean@example.com>\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",
             )
@@ -805,16 +738,16 @@ mod tests {
     #[test]
     fn issue_653() {
         let mut headers = Headers::new();
-        headers.insert_raw(
+        headers.insert_raw(HeaderValue::new(
             HeaderName::new_from_ascii_str("Subject"),
-            "＋仮名 :a;go; ;;;;;s;;;;;;;;;;;;;;;;fffeinmjgggggggggｆっ".to_string(),
+            "＋仮名 :a;go; ;;;;;s;;;;;;;;;;;;;;;;fffeinmjgggggggggｆっ".to_owned(),
-        );
+        ));
 
         assert_eq!(
             headers.to_string(),
             concat!(
-                "Subject: =?utf-8?b?77yL5Luu5ZCN?= :a;go; \r\n",
+                "Subject: =?utf-8?b?77yL5Luu5ZCN?= :a;go; =?utf-8?b?Ozs7OztzOzs7Ozs7Ozs7?=\r\n",
-                " =?utf-8?b?Ozs7OztzOzs7Ozs7Ozs7Ozs7Ozs7O2ZmZmVpbm1qZ2dnZ2dnZ2dn772G44Gj?=\r\n"
+                " =?utf-8?b?Ozs7Ozs7O2ZmZmVpbm1qZ2dnZ2dnZ2dn772G44Gj?=\r\n",
             )
         );
     }

src/message/header/special.rs

@@ -1,10 +1,10 @@
 use crate::{
-    message::header::{Header, HeaderName},
+    message::header::{Header, HeaderName, HeaderValue},
     BoxError,
 };
 
 /// Message format version, defined in [RFC2045](https://tools.ietf.org/html/rfc2045#section-4)
-#[derive(Debug, Copy, Clone, PartialEq)]
+#[derive(Debug, Copy, Clone, PartialEq, Eq)]
 pub struct MimeVersion {
     major: u8,
     minor: u8,
@@ -16,15 +16,18 @@ pub struct MimeVersion {
 pub const MIME_VERSION_1_0: MimeVersion = MimeVersion::new(1, 0);
 
 impl MimeVersion {
+    /// 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
@@ -50,8 +53,9 @@ impl Header for MimeVersion {
         Ok(MimeVersion::new(major, minor))
     }
 
-    fn display(&self) -> String {
+    fn display(&self) -> HeaderValue {
-        format!("{}.{}", self.major, self.minor)
+        let val = format!("{}.{}", self.major, self.minor);
+        HeaderValue::dangerous_new_pre_encoded(Self::name(), val.clone(), val)
     }
 }
 
@@ -63,8 +67,10 @@ impl Default for MimeVersion {
 
 #[cfg(test)]
 mod test {
+    use pretty_assertions::assert_eq;
+
     use super::{MimeVersion, MIME_VERSION_1_0};
-    use crate::message::header::{HeaderName, Headers};
+    use crate::message::header::{HeaderName, HeaderValue, Headers};
 
     #[test]
     fn format_mime_version() {
@@ -83,17 +89,17 @@ mod test {
     fn parse_mime_version() {
         let mut headers = Headers::new();
 
-        headers.insert_raw(
+        headers.insert_raw(HeaderValue::new(
             HeaderName::new_from_ascii_str("MIME-Version"),
-            "1.0".to_string(),
+            "1.0".to_owned(),
-        );
+        ));
 
         assert_eq!(headers.get::<MimeVersion>(), Some(MIME_VERSION_1_0));
 
-        headers.insert_raw(
+        headers.insert_raw(HeaderValue::new(
             HeaderName::new_from_ascii_str("MIME-Version"),
-            "0.1".to_string(),
+            "0.1".to_owned(),
-        );
+        ));
 
         assert_eq!(headers.get::<MimeVersion>(), Some(MimeVersion::new(0, 1)));
     }

src/message/header/textual.rs

@@ -1,10 +1,10 @@
-use super::{Header, HeaderName};
+use super::{Header, HeaderName, HeaderValue};
 use crate::BoxError;
 
 macro_rules! text_header {
     ($(#[$attr:meta])* Header($type_name: ident, $header_name: expr )) => {
         $(#[$attr])*
-        #[derive(Debug, Clone, PartialEq)]
+        #[derive(Debug, Clone, PartialEq, Eq)]
         pub struct $type_name(String);
 
         impl Header for $type_name {
@@ -16,8 +16,8 @@ macro_rules! text_header {
                 Ok(Self(s.into()))
             }
 
-            fn display(&self) -> String {
+            fn display(&self) -> HeaderValue {
-                self.0.clone()
+             HeaderValue::new(Self::name(),   self.0.clone())
             }
         }
 
@@ -85,8 +85,10 @@ text_header! {
 
 #[cfg(test)]
 mod test {
+    use pretty_assertions::assert_eq;
+
     use super::Subject;
-    use crate::message::header::{HeaderName, Headers};
+    use crate::message::header::{HeaderName, HeaderValue, Headers};
 
     #[test]
     fn format_ascii() {
@@ -107,13 +109,24 @@ mod test {
         );
     }
 
+    #[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.insert_raw(
+        headers.insert_raw(HeaderValue::new(
             HeaderName::new_from_ascii_str("Subject"),
-            "Sample subject".to_string(),
+            "Sample subject".to_owned(),
-        );
+        ));
 
         assert_eq!(
             headers.get::<Subject>(),

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

@@ -1,16 +1,21 @@
-use crate::address::{Address, AddressError};
 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
 ///
@@ -63,14 +68,30 @@ impl Mailbox {
     pub fn new(name: Option<String>, email: Address) -> Self {
         Mailbox { name, email }
     }
+
+    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('>');
@@ -89,40 +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('>')) {
+        let (name, (user, domain)) = parsers::mailbox().parse(src).map_err(|_errs| {
-            (Some(addr_open), Some(addr_close)) if addr_open < addr_close => {
+            // TODO: improve error management
-                let name = src.split_at(addr_open).0;
+            AddressError::InvalidInput
-                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 mailbox = Mailbox::new(name, Address::new(user, domain)?);
-                let name = name.trim();
+
-                let name = if name.is_empty() {
+        Ok(mailbox)
-                    None
-                } else {
-                    Some(name.into())
-                };
-                Ok(Mailbox::new(name, addr))
-            }
-            (Some(_), _) => Err(AddressError::Unbalanced),
-            _ => {
-                let addr = src.parse()?;
-                Ok(Mailbox::new(None, addr))
-            }
     }
+}
+
+impl From<Address> for Mailbox {
+    fn from(value: Address) -> Self {
+        Self::new(None, value)
     }
 }
 
@@ -130,7 +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>);
 
@@ -169,7 +174,7 @@ 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
     ///
@@ -250,6 +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 {
@@ -282,6 +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>;
@@ -291,14 +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();
@@ -320,17 +343,110 @@ impl FromStr for Mailboxes {
     type Err = AddressError;
 
     fn from_str(src: &str) -> Result<Self, Self::Err> {
-        src.split(',')
+        let mut mailboxes = Vec::new();
-            .map(|m| m.trim().parse())
+
-            .collect::<Result<Vec<_>, _>>()
+        let parsed_mailboxes = parsers::mailbox_list().parse(src).map_err(|_errs| {
-            .map(Mailboxes)
+            // 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() {
@@ -350,7 +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>"#
         );
     }
 
@@ -359,7 +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"
         );
@@ -372,7 +544,7 @@ mod test {
                 "{}",
                 Mailbox::new(Some(" K. ".into()), "kayo@example.com".parse().unwrap())
             ),
-            "K. <kayo@example.com>"
+            "\"K.\" <kayo@example.com>"
         );
     }
 
@@ -384,6 +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!(
@@ -395,6 +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!(
@@ -406,7 +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()))
         );
     }
@@ -414,7 +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

@@ -1,11 +1,11 @@
-use std::io::Write;
+use std::{io::Write, iter::repeat_with};
+
+use mime::Mime;
 
 use crate::message::{
     header::{self, ContentTransferEncoding, ContentType, Header, Headers},
     EmailFormat, IntoBody,
 };
-use mime::Mime;
-use std::iter::repeat_with;
 
 /// MIME part variants
 #[derive(Debug, Clone)]
@@ -17,6 +17,16 @@ pub(super) enum Part {
     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 {
@@ -100,14 +110,14 @@ impl SinglePart {
         SinglePartBuilder::new()
     }
 
-    /// Directly create a `SinglePart` from an plain UTF-8 content
+    /// 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)
     }
 
-    /// Directly create a `SinglePart` from an UTF-8 HTML content
+    /// 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)
@@ -132,6 +142,12 @@ impl SinglePart {
         self.format(&mut out);
         out
     }
+
+    /// 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 {
@@ -139,8 +155,7 @@ impl EmailFormat for SinglePart {
         write!(out, "{}", self.headers)
             .expect("A Write implementation panicked while formatting headers");
         out.extend_from_slice(b"\r\n");
-        out.extend_from_slice(&self.body);
+        self.format_body(out);
-        out.extend_from_slice(b"\r\n");
     }
 }
 
@@ -149,17 +164,17 @@ impl EmailFormat for SinglePart {
 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
@@ -190,9 +205,9 @@ impl MultiPartKind {
             },
             boundary,
             match self {
-                Self::Encrypted { protocol } => format!("; protocol=\"{}\"", protocol),
+                Self::Encrypted { protocol } => format!("; protocol=\"{protocol}\""),
                 Self::Signed { protocol, micalg } =>
-                    format!("; protocol=\"{}\"; micalg=\"{}\"", protocol, micalg),
+                    format!("; protocol=\"{protocol}\"; micalg=\"{micalg}\""),
                 _ => String::new(),
             }
         )
@@ -373,14 +388,9 @@ impl MultiPart {
         self.format(&mut out);
         out
     }
-}
-
-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");
 
+    /// Format only the multipart body
+    fn format_body(&self, out: &mut Vec<u8>) {
         let boundary = self.boundary();
 
         for part in &self.parts {
@@ -396,10 +406,20 @@ 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() {
@@ -477,7 +497,7 @@ mod test {
         assert_eq!(
             String::from_utf8(part.formatted()).unwrap(),
             concat!(
-                "Content-Type: multipart/mixed; \r\n",
+                "Content-Type: multipart/mixed;\r\n",
                 " boundary=\"0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\"\r\n",
                 "\r\n",
                 "--0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\r\n",
@@ -524,8 +544,8 @@ mod test {
         assert_eq!(
             String::from_utf8(part.formatted()).unwrap(),
             concat!(
-                "Content-Type: multipart/encrypted; \r\n",
+                "Content-Type: multipart/encrypted;\r\n",
-                " boundary=\"0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\"; \r\n",
+                " boundary=\"0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\";\r\n",
                 " protocol=\"application/pgp-encrypted\"\r\n",
                 "\r\n",
                 "--0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\r\n",
@@ -580,8 +600,8 @@ mod test {
         assert_eq!(
             String::from_utf8(part.formatted()).unwrap(),
             concat!(
-                "Content-Type: multipart/signed; \r\n",
+                "Content-Type: multipart/signed;\r\n",
-                " boundary=\"0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\"; \r\n",
+                " boundary=\"0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\";\r\n",
                 " protocol=\"application/pgp-signature\";",
                 " micalg=\"pgp-sha256\"\r\n",
                 "\r\n",
@@ -622,7 +642,7 @@ mod test {
                              .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; \r\n",
+                   concat!("Content-Type: multipart/alternative;\r\n",
                            " boundary=\"0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\"\r\n",
                            "\r\n",
                            "--0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\r\n",
@@ -660,11 +680,11 @@ mod test {
                              .body(String::from("int main() { return 0; }")));
 
         assert_eq!(String::from_utf8(part.formatted()).unwrap(),
-                   concat!("Content-Type: multipart/mixed; \r\n",
+                   concat!("Content-Type: multipart/mixed;\r\n",
                            " boundary=\"0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\"\r\n",
                            "\r\n",
                            "--0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\r\n",
-                           "Content-Type: multipart/related; \r\n",
+                           "Content-Type: multipart/related;\r\n",
                            " boundary=\"0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\"\r\n",
                            "\r\n",
                            "--0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\r\n",

src/message/mod.rs

@@ -14,7 +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>> {
@@ -23,6 +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(())
 //! # }
@@ -38,6 +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!
@@ -106,9 +108,10 @@
 //!
 //! ```rust
 //! # use std::error::Error;
-//! use lettre::message::{header, Attachment, Body, Message, MultiPart, SinglePart};
 //! use std::fs;
 //!
+//! use lettre::message::{header, Attachment, Body, Message, MultiPart, SinglePart};
+//!
 //! # fn main() -> Result<(), Box<dyn Error>> {
 //! let image = fs::read("docs/lettre.png")?;
 //! // this image_body can be cloned and reused between emails.
@@ -195,15 +198,19 @@
 //! ```
 //! </details>
 
-use std::{convert::TryFrom, io::Write, iter, time::SystemTime};
+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::*;
 
 mod attachment;
 mod body;
+#[cfg(feature = "dkim")]
+pub mod dkim;
 pub mod header;
 mod mailbox;
 mod mimebody;
@@ -227,6 +234,7 @@ trait EmailFormat {
 pub struct MessageBuilder {
     headers: Headers,
     envelope: Option<Envelope>,
+    drop_bcc: bool,
 }
 
 impl MessageBuilder {
@@ -235,24 +243,26 @@ impl MessageBuilder {
         Self {
             headers: Headers::new(),
             envelope: None,
+            drop_bcc: true,
         }
     }
 
-    /// Set custom header to message
+    /// Set or add mailbox to `From` header
-    pub fn header<H: Header>(mut self, header: H) -> Self {
+    ///
-        self.headers.set(header);
+    /// Defined in [RFC5322](https://tools.ietf.org/html/rfc5322#section-3.6.2).
-        self
+    ///
+    /// Shortcut for `self.mailbox(header::From(mbox))`.
+    pub fn from(self, mbox: Mailbox) -> Self {
+        self.mailbox(header::From::from(Mailboxes::from(mbox)))
     }
 
-    /// Add mailbox to header
+    /// Set `Sender` header. Should be used when providing several `From` mailboxes.
-    pub fn mailbox<H: Header + MailboxesHeader>(self, header: H) -> Self {
+    ///
-        match self.headers.get::<H>() {
+    /// Defined in [RFC5322](https://tools.ietf.org/html/rfc5322#section-3.6.2).
-            Some(mut header_) => {
+    ///
-                header_.join_mailboxes(header);
+    /// Shortcut for `self.header(header::Sender(mbox))`.
-                self.header(header_)
+    pub fn sender(self, mbox: Mailbox) -> Self {
-            }
+        self.header(header::Sender::from(mbox))
-            None => self.header(header),
-        }
     }
 
     /// Add `Date` header to message
@@ -267,42 +277,7 @@ impl MessageBuilder {
     /// Shortcut for `self.date(SystemTime::now())`, it is automatically inserted
     /// if no date has been provided.
     pub fn date_now(self) -> Self {
-        self.date(SystemTime::now())
+        self.date(crate::time::now())
-    }
-
-    /// 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 `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.
-    ///
-    /// 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))
-    }
-
-    /// Set or add mailbox to `From` header
-    ///
-    /// 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::from(Mailboxes::from(mbox)))
     }
 
     /// Set or add mailbox to `ReplyTo` header
@@ -347,6 +322,14 @@ impl MessageBuilder {
         self.header(header::References::from(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)
     ///
@@ -362,9 +345,9 @@ impl MessageBuilder {
                 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::from(
                     // https://tools.ietf.org/html/rfc5322#section-3.6.4
@@ -375,17 +358,48 @@ impl MessageBuilder {
     }
 
     /// 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::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)
     pub fn envelope(mut self, envelope: Envelope) -> Self {
         self.envelope = Some(envelope);
         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
@@ -418,8 +432,10 @@ impl MessageBuilder {
             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,
@@ -441,15 +457,24 @@ impl MessageBuilder {
         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
@@ -478,6 +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
@@ -489,6 +519,81 @@ 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 {
@@ -500,7 +605,7 @@ impl EmailFormat for Message {
             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);
             }
         }
     }
@@ -522,6 +627,8 @@ fn make_message_id() -> String {
 mod test {
     use std::time::{Duration, SystemTime};
 
+    use pretty_assertions::assert_eq;
+
     use super::{header, mailbox::Mailbox, make_message_id, Message, MultiPart, SinglePart};
 
     #[test]
@@ -532,7 +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())
@@ -550,7 +657,7 @@ mod test {
     }
 
     #[test]
-    fn email_message() {
+    fn email_message_no_bcc() {
         // Tue, 15 Nov 1994 08:12:31 GMT
         let date = SystemTime::UNIX_EPOCH + Duration::from_secs(784887151);
 
@@ -574,9 +681,47 @@ mod test {
         assert_eq!(
             String::from_utf8(email.formatted()).unwrap(),
             concat!(
-                "Date: Tue, 15 Nov 1994 08:12:31 -0000\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",
@@ -624,7 +769,7 @@ mod test {
                 continue;
             }
 
-            assert_eq!(line.0, line.1)
+            assert_eq!(line.0, line.1);
         }
     }
 

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(all(feature = "web", target_arch = "wasm32"))]
+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(all(feature = "web", target_arch = "wasm32")))]
+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

@@ -1,8 +1,9 @@
 //! Error and result type for file transport
 
-use crate::BoxError;
 use std::{error::Error as StdError, fmt};
 
+use crate::BoxError;
+
 /// The Errors that may occur when sending an email over SMTP
 pub struct Error {
     inner: Box<Inner>,
@@ -33,6 +34,7 @@ impl Error {
 
     /// Returns true if the error is an envelope serialization or deserialization error
     #[cfg(feature = "file-transport-envelope")]
+    #[cfg_attr(docsrs, doc(cfg(feature = "file-transport-envelope")))]
     pub fn is_envelope(&self) -> bool {
         matches!(self.inner.kind, Kind::Envelope)
     }
@@ -53,7 +55,7 @@ impl fmt::Debug for Error {
 
         builder.field("kind", &self.inner.kind);
 
-        if let Some(ref source) = self.inner.source {
+        if let Some(source) = &self.inner.source {
             builder.field("source", source);
         }
 
@@ -67,10 +69,10 @@ impl fmt::Display for Error {
             Kind::Io => f.write_str("response error")?,
             #[cfg(feature = "file-transport-envelope")]
             Kind::Envelope => f.write_str("internal client error")?,
-        };
+        }
 
-        if let Some(ref e) = self.inner.source {
+        if let Some(e) = &self.inner.source {
-            write!(f, ": {}", e)?;
+            write!(f, ": {e}")?;
         }
 
         Ok(())

src/transport/file/mod.rs

@@ -9,9 +9,10 @@
 //! #
 //! # #[cfg(all(feature = "file-transport", feature = "builder"))]
 //! # fn main() -> Result<(), Box<dyn Error>> {
-//! use lettre::{FileTransport, Message, Transport};
 //! use std::env::temp_dir;
 //!
+//! use lettre::{message::header::ContentType, FileTransport, Message, Transport};
+//!
 //! // Write to the local temp directory
 //! let sender = FileTransport::new(temp_dir());
 //! let email = Message::builder()
@@ -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);
+//! sender.send(&email)?;
-//! assert!(result.is_ok());
 //! # Ok(())
 //! # }
 //!
@@ -41,9 +42,10 @@
 //! #
 //! # #[cfg(all(feature = "file-transport-envelope", feature = "builder"))]
 //! # fn main() -> Result<(), Box<dyn Error>> {
-//! use lettre::{FileTransport, Message, Transport};
 //! use std::env::temp_dir;
 //!
+//! use lettre::{message::header::ContentType, FileTransport, Message, Transport};
+//!
 //! // Write to the local temp directory
 //! let sender = FileTransport::with_envelope(temp_dir());
 //! let email = Message::builder()
@@ -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);
+//! sender.send(&email)?;
-//! assert!(result.is_ok());
 //! # Ok(())
 //! # }
 //!
@@ -70,7 +72,10 @@
 //! # #[cfg(all(feature = "tokio1", feature = "file-transport", feature = "builder"))]
 //! # async fn run() -> Result<(), Box<dyn Error>> {
 //! use std::env::temp_dir;
-//! use lettre::{AsyncTransport, Tokio1Executor, Message, AsyncFileTransport};
+//!
+//! use lettre::{
+//!     message::header::ContentType, AsyncFileTransport, AsyncTransport, Message, Tokio1Executor,
+//! };
 //!
 //! // Write to the local temp directory
 //! let sender = AsyncFileTransport::<Tokio1Executor>::new(temp_dir());
@@ -79,10 +84,10 @@
 //!     .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).await;
+//! sender.send(email).await?;
-//! assert!(result.is_ok());
 //! # Ok(())
 //! # }
 //! ```
@@ -95,7 +100,11 @@
 //! # #[cfg(all(feature = "async-std1", feature = "file-transport", feature = "builder"))]
 //! # async fn run() -> Result<(), Box<dyn Error>> {
 //! use std::env::temp_dir;
-//! use lettre::{AsyncTransport, AsyncStd1Executor, Message, AsyncFileTransport};
+//!
+//! use lettre::{
+//!     message::header::ContentType, AsyncFileTransport, AsyncStd1Executor, AsyncTransport,
+//!     Message,
+//! };
 //!
 //! // Write to the local temp directory
 //! let sender = AsyncFileTransport::<AsyncStd1Executor>::new(temp_dir());
@@ -104,10 +113,10 @@
 //!     .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).await;
+//! sender.send(email).await?;
-//! assert!(result.is_ok());
 //! # 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!
@@ -132,26 +142,28 @@
 //! {"forward_path":["hei@domain.tld"],"reverse_path":"nobody@domain.tld"}
 //! ```
 
-pub use self::error::Error;
-use crate::{address::Envelope, Transport};
-#[cfg(any(feature = "async-std1", feature = "tokio1"))]
-use crate::{AsyncTransport, Executor};
-#[cfg(any(feature = "async-std1", 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 {
@@ -187,6 +199,7 @@ impl FileTransport {
     /// Writes the email content in eml format and the envelope
     /// in json format.
     #[cfg(feature = "file-transport-envelope")]
+    #[cfg_attr(docsrs, doc(cfg(feature = "file-transport-envelope")))]
     pub fn with_envelope<P: AsRef<Path>>(path: P) -> FileTransport {
         FileTransport {
             path: PathBuf::from(path.as_ref()),
@@ -199,21 +212,22 @@ impl FileTransport {
     ///
     /// Reads the envelope and the raw message content.
     #[cfg(feature = "file-transport-envelope")]
+    #[cfg_attr(docsrs, doc(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!("{}.eml", email_id));
+        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!("{}.json", email_id));
+        let json_file = self.path.join(format!("{email_id}.json"));
-        let json = fs::read(&json_file).map_err(error::io)?;
+        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}"))
     }
 }
 
@@ -237,6 +251,7 @@ where
     /// Writes the email content in eml format and the envelope
     /// in json format.
     #[cfg(feature = "file-transport-envelope")]
+    #[cfg_attr(docsrs, doc(cfg(feature = "file-transport-envelope")))]
     pub fn with_envelope<P: AsRef<Path>>(path: P) -> Self {
         Self {
             inner: FileTransport::with_envelope(path),
@@ -248,11 +263,12 @@ where
     ///
     /// Reads the envelope and the raw message content.
     #[cfg(feature = "file-transport-envelope")]
+    #[cfg_attr(docsrs, doc(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!("{}.eml", email_id));
+        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!("{}.json", email_id));
+        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)?;
 
@@ -260,6 +276,16 @@ where
     }
 }
 
+#[cfg(any(feature = "async-std1", feature = "tokio1"))]
+impl<E: Executor> Clone for AsyncFileTransport<E> {
+    fn clone(&self) -> Self {
+        Self {
+            inner: self.inner.clone(),
+            marker_: PhantomData,
+        }
+    }
+}
+
 impl Transport for FileTransport {
     type Ok = Id;
     type Error = Error;
@@ -270,6 +296,8 @@ impl Transport for FileTransport {
         let email_id = Uuid::new_v4();
 
         let file = self.path(&email_id, "eml");
+        #[cfg(feature = "tracing")]
+        tracing::debug!(?file, "writing email to");
         fs::write(file, email).map_err(error::io)?;
 
         #[cfg(feature = "file-transport-envelope")]
@@ -300,6 +328,8 @@ where
         let email_id = Uuid::new_v4();
 
         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")]

src/transport/mod.rs

@@ -32,7 +32,7 @@
 //! | [`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`]     | [`StubTransport`]          | Drops the email - Useful for debugging                  |
+//! | [`stub`]     | Debug    | [`StubTransport`]     | [`AsyncStubTransport`]     | Drops the email - Useful for debugging                  |
 //!
 //! ## Building an email
 //!
@@ -56,17 +56,20 @@
 //! #
 //! # #[cfg(all(feature = "builder", feature = "smtp-transport"))]
 //! # fn main() -> Result<(), Box<dyn Error>> {
-//! use lettre::transport::smtp::authentication::Credentials;
+//! use lettre::{
-//! use lettre::{Message, SmtpTransport, Transport};
+//!     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_string(), "smtp_password".to_string());
+//! 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")?
@@ -76,7 +79,7 @@
 //! // 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:?}"),
 //! }
 //! # Ok(())
 //! # }
@@ -98,6 +101,7 @@
 //! [`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;
@@ -128,11 +132,18 @@ pub trait Transport {
     #[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
@@ -150,10 +161,17 @@ pub trait AsyncTransport {
     #[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

@@ -1,8 +1,9 @@
 //! Error and result type for sendmail transport
 
-use crate::BoxError;
 use std::{error::Error as StdError, fmt};
 
+use crate::BoxError;
+
 /// The Errors that may occur when sending an email over sendmail
 pub struct Error {
     inner: Box<Inner>,
@@ -51,7 +52,7 @@ impl fmt::Debug for Error {
 
         builder.field("kind", &self.inner.kind);
 
-        if let Some(ref source) = self.inner.source {
+        if let Some(source) = &self.inner.source {
             builder.field("source", source);
         }
 
@@ -64,10 +65,10 @@ impl fmt::Display for Error {
         match self.inner.kind {
             Kind::Response => f.write_str("response error")?,
             Kind::Client => f.write_str("internal client error")?,
-        };
+        }
 
-        if let Some(ref e) = self.inner.source {
+        if let Some(e) = &self.inner.source {
-            write!(f, ": {}", e)?;
+            write!(f, ": {e}")?;
         }
 
         Ok(())

src/transport/sendmail/mod.rs

@@ -7,18 +7,18 @@
 //! #
 //! # #[cfg(all(feature = "sendmail-transport", feature = "builder"))]
 //! # fn main() -> Result<(), Box<dyn Error>> {
-//! use lettre::{Message, SendmailTransport, Transport};
+//! 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);
+//! sender.send(&email)?;
-//! assert!(result.is_ok());
 //! # Ok(())
 //! # }
 //!
@@ -33,18 +33,21 @@
 //! #
 //! # #[cfg(all(feature = "tokio1", feature = "sendmail-transport", feature = "builder"))]
 //! # async fn run() -> Result<(), Box<dyn Error>> {
-//! use lettre::{Message, AsyncTransport, Tokio1Executor, AsyncSendmailTransport, 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 = AsyncSendmailTransport::<Tokio1Executor>::new();
-//! let result = sender.send(email).await;
+//! sender.send(email).await?;
-//! assert!(result.is_ok());
 //! # Ok(())
 //! # }
 //! ```
@@ -56,22 +59,32 @@
 //! #
 //! # #[cfg(all(feature = "async-std1", feature = "sendmail-transport", feature = "builder"))]
 //! # async fn run() -> Result<(), Box<dyn Error>> {
-//! use lettre::{Message, AsyncTransport, AsyncStd1Executor, AsyncSendmailTransport};
+//! 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 = AsyncSendmailTransport::<AsyncStd1Executor>::new();
-//! let result = sender.send(email).await;
+//! sender.send(email).await?;
-//! assert!(result.is_ok());
 //! # Ok(())
 //! # }
 //! ```
 
+#[cfg(any(feature = "async-std1", feature = "tokio1"))]
+use std::marker::PhantomData;
+use std::{
+    ffi::OsString,
+    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;
@@ -80,15 +93,6 @@ use crate::Tokio1Executor;
 use crate::{address::Envelope, Transport};
 #[cfg(any(feature = "async-std1", feature = "tokio1"))]
 use crate::{AsyncTransport, Executor};
-#[cfg(any(feature = "async-std1", feature = "tokio1"))]
-use async_trait::async_trait;
-#[cfg(any(feature = "async-std1", feature = "tokio1"))]
-use std::marker::PhantomData;
-use std::{
-    ffi::OsString,
-    io::Write,
-    process::{Command, Stdio},
-};
 
 mod error;
 
@@ -116,7 +120,7 @@ impl SendmailTransport {
     /// 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].
+    /// use [`SendmailTransport::new_with_command`].
     pub fn new() -> SendmailTransport {
         SendmailTransport {
             command: DEFAULT_SENDMAIL.into(),
@@ -153,7 +157,7 @@ where
     /// 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].
+    /// use [`AsyncSendmailTransport::new_with_command`].
     pub fn new() -> Self {
         Self {
             inner: SendmailTransport::new(),
@@ -228,6 +232,9 @@ impl Transport for SendmailTransport {
     type Error = Error;
 
     fn send_raw(&self, envelope: &Envelope, email: &[u8]) -> Result<Self::Ok, Self::Error> {
+        #[cfg(feature = "tracing")]
+        tracing::debug!(command = ?self.command, "sending email with");
+
         // Spawn the sendmail command
         let mut process = self.command(envelope).spawn().map_err(error::client)?;
 
@@ -257,6 +264,9 @@ impl AsyncTransport for AsyncSendmailTransport<AsyncStd1Executor> {
     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
@@ -289,6 +299,9 @@ impl AsyncTransport for AsyncSendmailTransport<Tokio1Executor> {
     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

src/transport/smtp/async_transport.rs

@@ -1,7 +1,8 @@
+#[cfg(feature = "pool")]
+use std::sync::Arc;
 use std::{
     fmt::{self, Debug},
     marker::PhantomData,
-    sync::Arc,
     time::Duration,
 };
 
@@ -11,6 +12,12 @@ use async_trait::async_trait;
 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,
 };
@@ -23,6 +30,30 @@ use crate::Tokio1Executor;
 use crate::{Envelope, Executor};
 
 /// 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")]
@@ -44,10 +75,15 @@ impl AsyncTransport for AsyncSmtpTransport<Tokio1Executor> {
         let result = conn.send(envelope, email).await?;
 
         #[cfg(not(feature = "pool"))]
-        conn.quit().await?;
+        conn.abort().await;
 
         Ok(result)
     }
+
+    async fn shutdown(&self) {
+        #[cfg(feature = "pool")]
+        self.inner.shutdown().await;
+    }
 }
 
 #[cfg(feature = "async-std1")]
@@ -66,6 +102,11 @@ impl AsyncTransport for AsyncSmtpTransport<AsyncStd1Executor> {
 
         Ok(result)
     }
+
+    async fn shutdown(&self) {
+        #[cfg(feature = "pool")]
+        self.inner.shutdown().await;
+    }
 }
 
 impl<E> AsyncSmtpTransport<E>
@@ -80,16 +121,15 @@ where
     /// to validate TLS certificates.
     #[cfg(any(
         feature = "tokio1-native-tls",
-        feature = "tokio1-rustls-tls",
+        feature = "tokio1-rustls",
-        feature = "async-std1-native-tls",
+        feature = "async-std1-rustls"
-        feature = "async-std1-rustls-tls"
     ))]
     #[cfg_attr(
         docsrs,
         doc(cfg(any(
             feature = "tokio1-native-tls",
-            feature = "tokio1-rustls-tls",
+            feature = "tokio1-rustls",
-            feature = "async-std1-rustls-tls"
+            feature = "async-std1-rustls"
         )))
     )]
     pub fn relay(relay: &str) -> Result<AsyncSmtpTransportBuilder, Error> {
@@ -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.
@@ -115,16 +155,15 @@ where
     /// or emails will be sent to the server, protecting from downgrade attacks.
     #[cfg(any(
         feature = "tokio1-native-tls",
-        feature = "tokio1-rustls-tls",
+        feature = "tokio1-rustls",
-        feature = "async-std1-native-tls",
+        feature = "async-std1-rustls"
-        feature = "async-std1-rustls-tls"
     ))]
     #[cfg_attr(
         docsrs,
         doc(cfg(any(
             feature = "tokio1-native-tls",
-            feature = "tokio1-rustls-tls",
+            feature = "tokio1-rustls",
-            feature = "async-std1-rustls-tls"
+            feature = "async-std1-rustls"
         )))
     )]
     pub fn starttls_relay(relay: &str) -> Result<AsyncSmtpTransportBuilder, Error> {
@@ -150,28 +189,128 @@ where
     ///
     /// * No authentication
     /// * No TLS
-    /// * A 60 seconds timeout for smtp commands
+    /// * 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 info = SmtpInfo {
+        AsyncSmtpTransportBuilder::new(server)
-            server: server.into(),
-            ..Default::default()
-        };
-        AsyncSmtpTransportBuilder {
-            info,
-            #[cfg(feature = "pool")]
-            pool_config: PoolConfig::default(),
     }
+
+    /// 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
+    /// # const TOML: &str = 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 afterwards if a connection pool is not used.
+    /// 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?;
 
@@ -198,6 +337,9 @@ where
 {
     fn clone(&self) -> Self {
         Self {
+            #[cfg(feature = "pool")]
+            inner: Arc::clone(&self.inner),
+            #[cfg(not(feature = "pool"))]
             inner: self.inner.clone(),
         }
     }
@@ -215,13 +357,27 @@ pub struct AsyncSmtpTransportBuilder {
 
 /// 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
@@ -234,6 +390,17 @@ 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
@@ -246,21 +413,31 @@ impl AsyncSmtpTransportBuilder {
     }
 
     /// 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 = "tokio1-native-tls",
-        feature = "tokio1-rustls-tls",
+        feature = "tokio1-rustls",
-        feature = "async-std1-native-tls",
+        feature = "async-std1-rustls"
-        feature = "async-std1-rustls-tls"
     ))]
     #[cfg_attr(
         docsrs,
         doc(cfg(any(
             feature = "tokio1-native-tls",
-            feature = "tokio1-rustls-tls",
+            feature = "tokio1-rustls",
-            feature = "async-std1-rustls-tls"
+            feature = "async-std1-rustls"
         )))
     )]
-    pub fn tls(mut self, tls: super::Tls) -> Self {
+    pub fn tls(mut self, tls: Tls) -> Self {
         self.info.tls = tls;
         self
     }
@@ -293,7 +470,7 @@ impl AsyncSmtpTransportBuilder {
 }
 
 /// Build client
-pub struct AsyncSmtpClient<E> {
+pub(super) struct AsyncSmtpClient<E> {
     info: SmtpInfo,
     marker_: PhantomData<E>,
 }
@@ -305,7 +482,7 @@ where
     /// Creates a new connection directly usable to send emails
     ///
     /// Handles encryption and authentication
-    pub async fn connection(&self) -> Result<AsyncSmtpConnection, Error> {
+    pub(super) async fn connection(&self) -> Result<AsyncSmtpConnection, Error> {
         let mut conn = E::connect(
             &self.info.server,
             self.info.port,

src/transport/smtp/authentication.rs

@@ -1,8 +1,9 @@
 //! Provides limited SASL authentication mechanisms
 
-use crate::transport::smtp::error::{self, Error};
 use std::fmt::{self, Debug, Display, Formatter};
 
+use crate::transport::smtp::error::{self, Error};
+
 /// Accepted authentication mechanisms
 ///
 /// Trying LOGIN last as it is deprecated.
@@ -50,7 +51,7 @@ pub enum Mechanism {
     /// [RFC 4616](https://tools.ietf.org/html/rfc4616)
     Plain,
     /// LOGIN authentication mechanism
-    /// Obsolete but needed for some providers (like office365)
+    /// 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,
@@ -70,7 +71,7 @@ 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,
@@ -97,12 +98,18 @@ impl Mechanism {
                 let decoded_challenge = challenge
                     .ok_or_else(|| error::client("This mechanism does expect a challenge"))?;
 
-                if vec!["User Name", "Username:", "Username"].contains(&decoded_challenge) {
+                if contains_ignore_ascii_case(
-                    return Ok(credentials.authentication_identity.to_string());
+                    decoded_challenge,
+                    ["User Name", "Username:", "Username", "User Name\0"],
+                ) {
+                    return Ok(credentials.authentication_identity.clone());
                 }
 
-                if vec!["Password", "Password:"].contains(&decoded_challenge) {
+                if contains_ignore_ascii_case(
-                    return Ok(credentials.secret.to_string());
+                    decoded_challenge,
+                    ["Password", "Password:", "Password\0"],
+                ) {
+                    return Ok(credentials.secret.clone());
                 }
 
                 Err(error::client("Unrecognized challenge"))
@@ -118,6 +125,15 @@ 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};
@@ -126,7 +142,7 @@ 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(),
@@ -139,7 +155,7 @@ 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(),
@@ -152,13 +168,30 @@ 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(),
+            "username".to_owned(),
-            "vF9dft4qmTc2Nvb3RlckBhdHRhdmlzdGEuY29tCg==".to_string(),
+            "vF9dft4qmTc2Nvb3RlckBhdHRhdmlzdGEuY29tCg==".to_owned(),
         );
 
         assert_eq!(
@@ -171,7 +204,7 @@ 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

@@ -1,8 +1,17 @@
-use super::{AsyncNetworkStream, ClientCodec, TlsParameters};
+use std::{fmt::Display, net::IpAddr, time::Duration};
+
+use futures_util::io::{AsyncBufReadExt, AsyncWriteExt, BufReader};
+
+#[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},
@@ -10,11 +19,6 @@ use crate::{
     },
     Envelope,
 };
-use futures_util::io::{AsyncBufReadExt, AsyncWriteExt, BufReader};
-use std::{fmt::Display, time::Duration};
-
-#[cfg(feature = "tracing")]
-use super::escape_crlf;
 
 macro_rules! try_smtp (
     ($err: expr, $client: ident) => ({
@@ -32,6 +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,
@@ -40,21 +45,68 @@ 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 = "tokio1")]
+    #[cfg_attr(docsrs, doc(cfg(feature = "tokio1")))]
+    pub async fn connect_with_transport(
+        stream: Box<dyn AsyncTokioStream>,
+        hello_name: &ClientId,
+    ) -> Result<AsyncSmtpConnection, Error> {
+        #[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")]
+    #[cfg_attr(docsrs, doc(cfg(feature = "tokio1")))]
     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(server, timeout, tls_parameters).await?;
+        #[allow(deprecated)]
+        let stream =
+            AsyncNetworkStream::connect_tokio1(server, timeout, tls_parameters, local_address)
+                .await?;
         Self::connect_impl(stream, hello_name).await
     }
 
@@ -62,16 +114,19 @@ impl AsyncSmtpConnection {
     ///
     /// Sends EHLO and parses server information
     #[cfg(feature = "async-std1")]
+    #[cfg_attr(docsrs, doc(cfg(feature = "async-std1")))]
     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> {
+        #[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,
@@ -113,7 +168,7 @@ impl AsyncSmtpConnection {
             mail_options.push(MailParameter::SmtpUtfEight);
         }
 
-        // Check for non-ascii content in message
+        // Check for non-ascii content in the message
         if !email.is_ascii() {
             if !self.server_info().supports_feature(Extension::EightBitMime) {
                 return Err(error::client(
@@ -153,6 +208,12 @@ 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,
@@ -189,9 +250,11 @@ 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);
     }
@@ -206,7 +269,7 @@ 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],
@@ -295,7 +358,10 @@ impl AsyncSmtpConnection {
                     return if response.is_positive() {
                         Ok(response)
                     } else {
-                        Err(error::code(response.code()))
+                        Err(error::code(
+                            response.code(),
+                            Some(response.message().collect()),
+                        ))
                     }
                 }
                 Err(nom::Err::Failure(e)) => {
@@ -310,4 +376,38 @@ impl AsyncSmtpConnection {
 
         Err(error::response("incomplete response"))
     }
+
+    /// The X509 certificate of the server (DER encoded)
+    #[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 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")]
+    #[cfg_attr(docsrs, doc(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"))]
+    #[cfg_attr(docsrs, doc(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

@@ -1,76 +1,97 @@
 use std::{
-    io, mem,
+    fmt, io, mem,
-    net::SocketAddr,
+    net::{IpAddr, SocketAddr},
     pin::Pin,
     task::{Context, Poll},
     time::Duration,
 };
 
-use futures_io::{
-    AsyncRead as FuturesAsyncRead, AsyncWrite as FuturesAsyncWrite, Error as IoError, ErrorKind,
-    Result as IoResult,
-};
-#[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, ToSocketAddrs as AsyncStd1ToSocketAddrs};
+use futures_io::{
+    AsyncRead as FuturesAsyncRead, AsyncWrite as FuturesAsyncWrite, Error as IoError,
+    Result as IoResult,
+};
+#[cfg(feature = "async-std1-rustls")]
+use futures_rustls::client::TlsStream as AsyncStd1RustlsStream;
+#[cfg(feature = "tokio1-boring-tls")]
+use tokio1_boring::SslStream as Tokio1SslStream;
 #[cfg(feature = "tokio1")]
-use tokio1_crate::net::{TcpStream as Tokio1TcpStream, ToSocketAddrs as Tokio1ToSocketAddrs};
+use tokio1_crate::io::{AsyncRead, AsyncWrite, ReadBuf as Tokio1ReadBuf};
-
+#[cfg(feature = "tokio1")]
-#[cfg(feature = "async-std1-native-tls")]
+use tokio1_crate::net::{
-use async_native_tls::TlsStream as AsyncStd1TlsStream;
+    TcpSocket as Tokio1TcpSocket, TcpStream as Tokio1TcpStream,
+    ToSocketAddrs as Tokio1ToSocketAddrs,
+};
 #[cfg(feature = "tokio1-native-tls")]
 use tokio1_native_tls_crate::TlsStream as Tokio1TlsStream;
-
+#[cfg(feature = "tokio1-rustls")]
-#[cfg(feature = "async-std1-rustls-tls")]
+use tokio1_rustls::client::TlsStream as Tokio1RustlsStream;
-use futures_rustls::client::TlsStream as AsyncStd1RustlsTlsStream;
-#[cfg(feature = "tokio1-rustls-tls")]
-use tokio1_rustls::client::TlsStream as Tokio1RustlsTlsStream;
 
 #[cfg(any(
     feature = "tokio1-native-tls",
-    feature = "tokio1-rustls-tls",
+    feature = "tokio1-rustls",
-    feature = "async-std1-native-tls",
+    feature = "tokio1-boring-tls",
-    feature = "async-std1-rustls-tls"
+    feature = "async-std1-rustls"
 ))]
 use super::InnerTlsParameters;
 use super::TlsParameters;
+#[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 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")]
+    #[cfg(feature = "tokio1-rustls")]
-    Tokio1RustlsTls(Tokio1RustlsTlsStream<Tokio1TcpStream>),
+    Tokio1Rustls(Tokio1RustlsStream<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")]
+    #[cfg(feature = "async-std1-rustls")]
-    AsyncStd1NativeTls(AsyncStd1TlsStream<AsyncStd1TcpStream>),
+    AsyncStd1Rustls(AsyncStd1RustlsStream<AsyncStd1TcpStream>),
-    /// Encrypted Tokio 1.x TCP stream
-    #[cfg(feature = "async-std1-rustls-tls")]
-    AsyncStd1RustlsTls(AsyncStd1RustlsTlsStream<AsyncStd1TcpStream>),
     /// Can't be built
     None,
 }
 
+#[allow(deprecated)]
 impl AsyncNetworkStream {
     fn new(inner: InnerAsyncNetworkStream) -> Self {
         if let InnerAsyncNetworkStream::None = inner {
@@ -82,25 +103,24 @@ impl AsyncNetworkStream {
 
     /// Returns peer's address
     pub fn peer_addr(&self) -> IoResult<SocketAddr> {
-        match self.inner {
+        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")]
+            #[cfg(feature = "tokio1-rustls")]
-            InnerAsyncNetworkStream::Tokio1RustlsTls(ref s) => s.get_ref().0.peer_addr(),
+            InnerAsyncNetworkStream::Tokio1Rustls(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(),
+            InnerAsyncNetworkStream::AsyncStd1Tcp(s) => s.peer_addr(),
-            #[cfg(feature = "async-std1-native-tls")]
+            #[cfg(feature = "async-std1-rustls")]
-            InnerAsyncNetworkStream::AsyncStd1NativeTls(ref s) => s.get_ref().peer_addr(),
+            InnerAsyncNetworkStream::AsyncStd1Rustls(s) => s.get_ref().0.peer_addr(),
-            #[cfg(feature = "async-std1-rustls-tls")]
-            InnerAsyncNetworkStream::AsyncStd1RustlsTls(ref s) => s.get_ref().0.peer_addr(),
             InnerAsyncNetworkStream::None => {
                 debug_assert!(false, "InnerAsyncNetworkStream::None must never be built");
-                Err(IoError::new(
+                Err(IoError::other(
-                    ErrorKind::Other,
                     "InnerAsyncNetworkStream::None must never be built",
                 ))
             }
@@ -108,23 +128,45 @@ impl AsyncNetworkStream {
     }
 
     #[cfg(feature = "tokio1")]
+    #[cfg_attr(docsrs, doc(cfg(feature = "tokio1")))]
+    pub fn use_existing_tokio1(stream: Box<dyn AsyncTokioStream>) -> AsyncNetworkStream {
+        AsyncNetworkStream::new(InnerAsyncNetworkStream::Tokio1Tcp(stream))
+    }
+
+    #[cfg(feature = "tokio1")]
+    #[cfg_attr(docsrs, doc(cfg(feature = "tokio1")))]
     pub async fn connect_tokio1<T: Tokio1ToSocketAddrs>(
         server: T,
         timeout: Option<Duration>,
         tls_parameters: Option<TlsParameters>,
+        local_addr: Option<IpAddr>,
     ) -> Result<AsyncNetworkStream, Error> {
-        async fn try_connect_timeout<T: Tokio1ToSocketAddrs>(
+        async fn try_connect<T: Tokio1ToSocketAddrs>(
             server: T,
-            timeout: Duration,
+            timeout: Option<Duration>,
+            local_addr: Option<IpAddr>,
         ) -> Result<Tokio1TcpStream, Error> {
             let addrs = tokio1_crate::net::lookup_host(server)
                 .await
-                .map_err(error::connection)?;
+                .map_err(error::connection)?
+                .filter(|resolved_addr| resolved_address_filter(resolved_addr, local_addr));
 
             let mut last_err = None;
 
             for addr in addrs {
-                let connect_future = Tokio1TcpStream::connect(&addr);
+                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),
@@ -132,25 +174,26 @@ impl AsyncNetworkStream {
                             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 address"),
+                None => error::connection("could not resolve to any supported address"),
             })
         }
 
-        let tcp_stream = match timeout {
+        let tcp_stream = try_connect(server, timeout, local_addr).await?;
-            Some(t) => try_connect_timeout(server, t).await?,
+        let mut stream =
-            None => Tokio1TcpStream::connect(server)
+            AsyncNetworkStream::new(InnerAsyncNetworkStream::Tokio1Tcp(Box::new(tcp_stream)));
-                .await
-                .map_err(error::connection)?,
-        };
-
-        let mut stream = AsyncNetworkStream::new(InnerAsyncNetworkStream::Tokio1Tcp(tcp_stream));
         if let Some(tls_parameters) = tls_parameters {
             stream.upgrade_tls(tls_parameters).await?;
         }
@@ -158,11 +201,15 @@ impl AsyncNetworkStream {
     }
 
     #[cfg(feature = "async-std1")]
+    #[cfg_attr(docsrs, doc(cfg(feature = "async-std1")))]
     pub async fn connect_asyncstd1<T: AsyncStd1ToSocketAddrs>(
         server: T,
         timeout: Option<Duration>,
         tls_parameters: Option<TlsParameters>,
     ) -> Result<AsyncNetworkStream, Error> {
+        // 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,
@@ -180,7 +227,7 @@ impl AsyncNetworkStream {
                         last_err = Some(io::Error::new(
                             io::ErrorKind::TimedOut,
                             "connection timed out",
-                        ))
+                        ));
                     }
                 }
             }
@@ -209,20 +256,27 @@ impl AsyncNetworkStream {
         match &self.inner {
             #[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 = mem::replace(&mut self.inner, InnerAsyncNetworkStream::None);
-                let tcp_stream = match tcp_stream {
+                let InnerAsyncNetworkStream::Tokio1Tcp(tcp_stream) = tcp_stream else {
-                    InnerAsyncNetworkStream::Tokio1Tcp(tcp_stream) => tcp_stream,
+                    unreachable!()
-                    _ => unreachable!(),
                 };
 
                 self.inner = Self::upgrade_tokio1_tls(tcp_stream, tls_parameters)
@@ -230,22 +284,18 @@ impl AsyncNetworkStream {
                     .map_err(error::connection)?;
                 Ok(())
             }
-            #[cfg(all(
+            #[cfg(all(feature = "async-std1", not(feature = "async-std1-rustls")))]
-                feature = "async-std1",
-                not(any(feature = "async-std1-native-tls", feature = "async-std1-rustls-tls"))
-            ))]
             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 = mem::replace(&mut self.inner, InnerAsyncNetworkStream::None);
-                let tcp_stream = match tcp_stream {
+                let InnerAsyncNetworkStream::AsyncStd1Tcp(tcp_stream) = tcp_stream else {
-                    InnerAsyncNetworkStream::AsyncStd1Tcp(tcp_stream) => tcp_stream,
+                    unreachable!()
-                    _ => unreachable!(),
                 };
 
                 self.inner = Self::upgrade_asyncstd1_tls(tcp_stream, tls_parameters)
@@ -258,16 +308,18 @@ impl AsyncNetworkStream {
     }
 
     #[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,
+        tcp_stream: Box<dyn AsyncTokioStream>,
         tls_parameters: TlsParameters,
     ) -> Result<InnerAsyncNetworkStream, Error> {
-        let domain = tls_parameters.domain().to_string();
+        match tls_parameters.inner {
-
-        match tls_parameters.connector {
             #[cfg(feature = "native-tls")]
-            InnerTlsParameters::NativeTls(connector) => {
+            InnerTlsParameters::NativeTls(inner) => {
                 #[cfg(not(feature = "tokio1-native-tls"))]
                 panic!("built without the tokio1-native-tls feature");
 
@@ -275,123 +327,229 @@ impl AsyncNetworkStream {
                 return {
                     use tokio1_native_tls_crate::TlsConnector;
 
-                    let connector = TlsConnector::from(connector);
+                    let connector = TlsConnector::from(inner.connector);
                     let stream = connector
-                        .connect(&domain, tcp_stream)
+                        .connect(&inner.server_name, tcp_stream)
                         .await
                         .map_err(error::connection)?;
                     Ok(InnerAsyncNetworkStream::Tokio1NativeTls(stream))
                 };
             }
-            #[cfg(feature = "rustls-tls")]
+            #[cfg(feature = "rustls")]
-            InnerTlsParameters::RustlsTls(config) => {
+            InnerTlsParameters::Rustls(inner) => {
-                #[cfg(not(feature = "tokio1-rustls-tls"))]
+                #[cfg(not(feature = "tokio1-rustls"))]
-                panic!("built without the tokio1-rustls-tls feature");
+                panic!("built without the tokio1-rustls feature");
 
-                #[cfg(feature = "tokio1-rustls-tls")]
+                #[cfg(feature = "tokio1-rustls")]
                 return {
-                    use std::convert::TryFrom;
-
-                    use rustls::ServerName;
                     use tokio1_rustls::TlsConnector;
 
-                    let domain = ServerName::try_from(domain.as_str())
+                    let connector = TlsConnector::from(inner.connector);
-                        .map_err(|_| error::connection("domain isn't a valid DNS name"))?;
-
-                    let connector = TlsConnector::from(config);
                     let stream = connector
-                        .connect(domain, tcp_stream)
+                        .connect(inner.server_name.inner(), tcp_stream)
                         .await
                         .map_err(error::connection)?;
-                    Ok(InnerAsyncNetworkStream::Tokio1RustlsTls(stream))
+                    Ok(InnerAsyncNetworkStream::Tokio1Rustls(stream))
+                };
+            }
+            #[cfg(feature = "boring-tls")]
+            InnerTlsParameters::BoringTls(inner) => {
+                #[cfg(not(feature = "tokio1-boring-tls"))]
+                panic!("built without the tokio1-boring-tls feature");
+
+                #[cfg(feature = "tokio1-boring-tls")]
+                return {
+                    let mut config = inner.connector.configure().map_err(error::connection)?;
+                    config.set_verify_hostname(inner.extra_info.accept_invalid_hostnames);
+
+                    let stream = tokio1_boring::connect(config, &inner.server_name, 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,
+        tls_parameters: TlsParameters,
     ) -> Result<InnerAsyncNetworkStream, Error> {
-        let domain = mem::take(&mut tls_parameters.domain);
+        match tls_parameters.inner {
-
-        match tls_parameters.connector {
             #[cfg(feature = "native-tls")]
-            InnerTlsParameters::NativeTls(connector) => {
+            InnerTlsParameters::NativeTls(_) => {
                 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) => {
+            InnerTlsParameters::Rustls(inner) => {
-                #[cfg(not(feature = "async-std1-rustls-tls"))]
+                #[cfg(not(feature = "async-std1-rustls"))]
-                panic!("built without the async-std1-rustls-tls feature");
+                panic!("built without the async-std1-rustls feature");
 
-                #[cfg(feature = "async-std1-rustls-tls")]
+                #[cfg(feature = "async-std1-rustls")]
                 return {
-                    use std::convert::TryFrom;
-
                     use futures_rustls::TlsConnector;
-                    use rustls::ServerName;
 
-                    let domain = ServerName::try_from(domain.as_str())
+                    let connector = TlsConnector::from(inner.connector);
-                        .map_err(|_| error::connection("domain isn't a valid DNS name"))?;
-
-                    let connector = TlsConnector::from(config);
                     let stream = connector
-                        .connect(domain, tcp_stream)
+                        .connect(inner.server_name.inner(), tcp_stream)
                         .await
                         .map_err(error::connection)?;
-                    Ok(InnerAsyncNetworkStream::AsyncStd1RustlsTls(stream))
+                    Ok(InnerAsyncNetworkStream::AsyncStd1Rustls(stream))
                 };
             }
+            #[cfg(feature = "boring-tls")]
+            InnerTlsParameters::BoringTls(_inner) => {
+                panic!("boring-tls isn't supported with async-std yet.");
+            }
         }
     }
 
     pub fn is_encrypted(&self) -> bool {
-        match self.inner {
+        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,
+            InnerAsyncNetworkStream::Tokio1Rustls(_) => true,
+            #[cfg(feature = "tokio1-boring-tls")]
+            InnerAsyncNetworkStream::Tokio1BoringTls(_) => true,
             #[cfg(feature = "async-std1")]
             InnerAsyncNetworkStream::AsyncStd1Tcp(_) => false,
-            #[cfg(feature = "async-std1-native-tls")]
+            #[cfg(feature = "async-std1-rustls")]
-            InnerAsyncNetworkStream::AsyncStd1NativeTls(_) => true,
+            InnerAsyncNetworkStream::AsyncStd1Rustls(_) => true,
-            #[cfg(feature = "async-std1-rustls-tls")]
-            InnerAsyncNetworkStream::AsyncStd1RustlsTls(_) => true,
             InnerAsyncNetworkStream::None => false,
         }
     }
+
+    #[cfg(feature = "boring-tls")]
+    #[cfg_attr(docsrs, doc(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::Tokio1Rustls(_) => 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::AsyncStd1Rustls(_) => 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::Tokio1Rustls(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::AsyncStd1Rustls(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::Tokio1Rustls(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::AsyncStd1Rustls(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 {
+        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())),
@@ -400,7 +558,7 @@ 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())),
@@ -408,8 +566,17 @@ impl FuturesAsyncRead for AsyncNetworkStream {
                     Poll::Pending => Poll::Pending,
                 }
             }
-            #[cfg(feature = "tokio1-rustls-tls")]
+            #[cfg(feature = "tokio1-rustls")]
-            InnerAsyncNetworkStream::Tokio1RustlsTls(ref mut s) => {
+            InnerAsyncNetworkStream::Tokio1Rustls(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())),
@@ -418,15 +585,9 @@ impl FuturesAsyncRead for AsyncNetworkStream {
                 }
             }
             #[cfg(feature = "async-std1")]
-            InnerAsyncNetworkStream::AsyncStd1Tcp(ref mut s) => Pin::new(s).poll_read(cx, buf),
+            InnerAsyncNetworkStream::AsyncStd1Tcp(s) => Pin::new(s).poll_read(cx, buf),
-            #[cfg(feature = "async-std1-native-tls")]
+            #[cfg(feature = "async-std1-rustls")]
-            InnerAsyncNetworkStream::AsyncStd1NativeTls(ref mut s) => {
+            InnerAsyncNetworkStream::AsyncStd1Rustls(s) => Pin::new(s).poll_read(cx, buf),
-                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::None => {
                 debug_assert!(false, "InnerAsyncNetworkStream::None must never be built");
                 Poll::Ready(Ok(0))
@@ -435,29 +596,26 @@ 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 {
+        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),
+            InnerAsyncNetworkStream::Tokio1NativeTls(s) => Pin::new(s).poll_write(cx, buf),
-            #[cfg(feature = "tokio1-rustls-tls")]
+            #[cfg(feature = "tokio1-rustls")]
-            InnerAsyncNetworkStream::Tokio1RustlsTls(ref mut s) => Pin::new(s).poll_write(cx, buf),
+            InnerAsyncNetworkStream::Tokio1Rustls(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),
+            InnerAsyncNetworkStream::AsyncStd1Tcp(s) => Pin::new(s).poll_write(cx, buf),
-            #[cfg(feature = "async-std1-native-tls")]
+            #[cfg(feature = "async-std1-rustls")]
-            InnerAsyncNetworkStream::AsyncStd1NativeTls(ref mut s) => {
+            InnerAsyncNetworkStream::AsyncStd1Rustls(s) => Pin::new(s).poll_write(cx, buf),
-                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::None => {
                 debug_assert!(false, "InnerAsyncNetworkStream::None must never be built");
                 Poll::Ready(Ok(0))
@@ -466,19 +624,19 @@ impl FuturesAsyncWrite for AsyncNetworkStream {
     }
 
     fn poll_flush(mut self: Pin<&mut Self>, cx: &mut Context<'_>) -> Poll<IoResult<()>> {
-        match self.inner {
+        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),
+            InnerAsyncNetworkStream::Tokio1NativeTls(s) => Pin::new(s).poll_flush(cx),
-            #[cfg(feature = "tokio1-rustls-tls")]
+            #[cfg(feature = "tokio1-rustls")]
-            InnerAsyncNetworkStream::Tokio1RustlsTls(ref mut s) => Pin::new(s).poll_flush(cx),
+            InnerAsyncNetworkStream::Tokio1Rustls(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),
+            InnerAsyncNetworkStream::AsyncStd1Tcp(s) => Pin::new(s).poll_flush(cx),
-            #[cfg(feature = "async-std1-native-tls")]
+            #[cfg(feature = "async-std1-rustls")]
-            InnerAsyncNetworkStream::AsyncStd1NativeTls(ref mut s) => Pin::new(s).poll_flush(cx),
+            InnerAsyncNetworkStream::AsyncStd1Rustls(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::None => {
                 debug_assert!(false, "InnerAsyncNetworkStream::None must never be built");
                 Poll::Ready(Ok(()))
@@ -487,19 +645,19 @@ impl FuturesAsyncWrite for AsyncNetworkStream {
     }
 
     fn poll_close(mut self: Pin<&mut Self>, cx: &mut Context<'_>) -> Poll<IoResult<()>> {
-        match self.inner {
+        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),
+            InnerAsyncNetworkStream::Tokio1NativeTls(s) => Pin::new(s).poll_shutdown(cx),
-            #[cfg(feature = "tokio1-rustls-tls")]
+            #[cfg(feature = "tokio1-rustls")]
-            InnerAsyncNetworkStream::Tokio1RustlsTls(ref mut s) => Pin::new(s).poll_shutdown(cx),
+            InnerAsyncNetworkStream::Tokio1Rustls(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),
+            InnerAsyncNetworkStream::AsyncStd1Tcp(s) => Pin::new(s).poll_close(cx),
-            #[cfg(feature = "async-std1-native-tls")]
+            #[cfg(feature = "async-std1-rustls")]
-            InnerAsyncNetworkStream::AsyncStd1NativeTls(ref mut s) => Pin::new(s).poll_close(cx),
+            InnerAsyncNetworkStream::AsyncStd1Rustls(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::None => {
                 debug_assert!(false, "InnerAsyncNetworkStream::None must never be built");
                 Poll::Ready(Ok(()))

src/transport/smtp/client/connection.rs

@@ -1,16 +1,18 @@
 use std::{
     fmt::Display,
     io::{self, BufRead, BufReader, Write},
-    net::ToSocketAddrs,
+    net::{IpAddr, ToSocketAddrs},
     time::Duration,
 };
 
+#[cfg(feature = "tracing")]
+use super::escape_crlf;
 use super::{ClientCodec, NetworkStream, TlsParameters};
 use crate::{
     address::Envelope,
     transport::smtp::{
         authentication::{Credentials, Mechanism},
-        commands::*,
+        commands::{Auth, Data, Ehlo, Mail, Noop, Quit, Rcpt, Starttls},
         error,
         error::Error,
         extension::{ClientId, Extension, MailBodyParameter, MailParameter, ServerInfo},
@@ -18,9 +20,6 @@ use crate::{
     },
 };
 
-#[cfg(feature = "tracing")]
-use super::escape_crlf;
-
 macro_rules! try_smtp (
     ($err: expr, $client: ident) => ({
         match $err {
@@ -45,6 +44,7 @@ pub struct SmtpConnection {
 }
 
 impl SmtpConnection {
+    /// Get information about the server
     pub fn server_info(&self) -> &ServerInfo {
         &self.server_info
     }
@@ -59,8 +59,9 @@ 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,
@@ -99,7 +100,7 @@ impl SmtpConnection {
             mail_options.push(MailParameter::SmtpUtfEight);
         }
 
-        // Check for non-ascii content in message
+        // Check for non-ascii content in the message
         if !email.is_ascii() {
             if !self.server_info().supports_feature(Extension::EightBitMime) {
                 return Err(error::client(
@@ -142,7 +143,7 @@ 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);
                 self.stream.get_mut().upgrade_tls(tls_parameters)?;
@@ -152,7 +153,7 @@ impl SmtpConnection {
                 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");
@@ -178,6 +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
@@ -201,7 +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],
@@ -237,11 +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()
     }
 
@@ -276,7 +279,10 @@ impl SmtpConnection {
                     return if response.is_positive() {
                         Ok(response)
                     } else {
-                        Err(error::code(response.code()))
+                        Err(error::code(
+                            response.code(),
+                            Some(response.message().collect()),
+                        ))
                     };
                 }
                 Err(nom::Err::Failure(e)) => {
@@ -291,4 +297,38 @@ impl SmtpConnection {
 
         Err(error::response("incomplete response"))
     }
+
+    /// The X509 certificate of the server (DER encoded)
+    #[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 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")]
+    #[cfg_attr(docsrs, doc(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"))]
+    #[cfg_attr(docsrs, doc(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/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 hello = ClientId::Domain("my_hostname".to_owned());
-//! let mut client = SmtpConnection::connect(&("localhost", SMTP_PORT), None, &hello, None)?;
+//! let mut client = SmtpConnection::connect(&("localhost", SMTP_PORT), None, &hello, None, None)?;
-//! client.command(
+//! client.command(Mail::new(Some("user@example.com".parse()?), vec![]))?;
-//!         Mail::new(Some("user@example.com".parse()?), vec![])
+//! client.command(Rcpt::new("user@example.org".parse()?, vec![]))?;
-//!     )?;
-//! client.command(
-//!         Rcpt::new("user@example.org".parse()?, vec![])
-//!       )?;
 //! client.command(Data)?;
 //! client.message("Test email".as_bytes())?;
 //! client.command(Quit)?;
@@ -28,15 +26,22 @@
 use std::fmt::Debug;
 
 #[cfg(any(feature = "tokio1", feature = "async-std1"))]
-pub(crate) use self::async_connection::AsyncSmtpConnection;
+pub use self::async_connection::AsyncSmtpConnection;
 #[cfg(any(feature = "tokio1", feature = "async-std1"))]
-pub(crate) use self::async_net::AsyncNetworkStream;
+#[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;
+pub(super) use self::tls::current::InnerTlsParameters;
+#[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+pub use self::tls::current::TlsVersion;
 pub use self::{
     connection::SmtpConnection,
-    tls::{Certificate, Tls, TlsParameters, TlsParametersBuilder},
+    tls::current::{
+        Certificate, CertificateStore, Identity, Tls, TlsParameters, TlsParametersBuilder,
+    },
 };
 
 #[cfg(any(feature = "tokio1", feature = "async-std1"))]
@@ -48,60 +53,57 @@ mod net;
 mod tls;
 
 /// The codec used for transparency
-#[derive(Default, Clone, Copy, Debug)]
+#[derive(Debug)]
-#[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 struct ClientCodec {
-    escape_count: u8,
+    status: CodecStatus,
 }
 
 impl ClientCodec {
     /// Creates a new client codec
-    pub fn new() -> Self {
+    pub(crate) fn new() -> Self {
-        ClientCodec::default()
+        Self {
+            status: CodecStatus::StartOfNewLine,
+        }
     }
 
     /// Adds transparency
     fn encode(&mut self, frame: &[u8], buf: &mut Vec<u8>) {
-        match frame.len() {
+        for &b in frame {
-            0 => {
+            buf.push(b);
-                match self.escape_count {
+            match (b, self.status) {
-                    0 => buf.extend_from_slice(b"\r\n.\r\n"),
+                (b'\r', _) => {
-                    1 => buf.extend_from_slice(b"\n.\r\n"),
+                    self.status = CodecStatus::StartingNewLine;
-                    2 => buf.extend_from_slice(b".\r\n"),
-                    _ => unreachable!(),
                 }
-                self.escape_count = 0;
+                (b'\n', CodecStatus::StartingNewLine) => {
+                    self.status = CodecStatus::StartOfNewLine;
                 }
-            _ => {
+                (_, CodecStatus::StartingNewLine) => {
-                let mut start = 0;
+                    self.status = CodecStatus::MiddleOfLine;
-                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 if *byte == b'\r' {
-                                1
-                            } else {
-                                0
                 }
+                (b'.', CodecStatus::StartOfNewLine) => {
+                    self.status = CodecStatus::MiddleOfLine;
+                    buf.push(b'.');
                 }
-                        _ => unreachable!(),
+                (_, CodecStatus::StartOfNewLine) => {
+                    self.status = CodecStatus::MiddleOfLine;
                 }
-                    if self.escape_count == 3 {
+                _ => {}
-                        self.escape_count = 0;
-                        buf.extend_from_slice(&frame[start..idx]);
-                        buf.extend_from_slice(b".");
-                        start = idx;
-                    }
-                }
-                buf.extend_from_slice(&frame[start..]);
             }
         }
     }
 }
 
+#[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")]
@@ -115,9 +117,10 @@ 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);
@@ -128,14 +131,18 @@ 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\ntest\r\n\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

@@ -1,19 +1,21 @@
-#[cfg(feature = "rustls-tls")]
+#[cfg(feature = "rustls")]
-use std::convert::TryFrom;
+use std::sync::Arc;
 use std::{
     io::{self, Read, Write},
     mem,
-    net::{Ipv4Addr, Shutdown, SocketAddr, SocketAddrV4, TcpStream, ToSocketAddrs},
+    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::{ClientConnection, StreamOwned};
+use socket2::{Domain, Protocol, Type};
 
-#[cfg(feature = "rustls-tls")]
+#[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
-use rustls::{ClientConnection, ServerName, StreamOwned};
-
-#[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
 use super::InnerTlsParameters;
 use super::TlsParameters;
 use crate::transport::smtp::{error, Error};
@@ -34,8 +36,10 @@ enum InnerNetworkStream {
     #[cfg(feature = "native-tls")]
     NativeTls(TlsStream<TcpStream>),
     /// Encrypted TCP stream
-    #[cfg(feature = "rustls-tls")]
+    #[cfg(feature = "rustls")]
-    RustlsTls(StreamOwned<ClientConnection, TcpStream>),
+    Rustls(StreamOwned<ClientConnection, TcpStream>),
+    #[cfg(feature = "boring-tls")]
+    BoringTls(SslStream<TcpStream>),
     /// Can't be built
     None,
 }
@@ -51,12 +55,14 @@ impl NetworkStream {
 
     /// Returns peer's address
     pub fn peer_addr(&self) -> io::Result<SocketAddr> {
-        match self.inner {
+        match &self.inner {
-            InnerNetworkStream::Tcp(ref s) => s.peer_addr(),
+            InnerNetworkStream::Tcp(s) => s.peer_addr(),
             #[cfg(feature = "native-tls")]
-            InnerNetworkStream::NativeTls(ref s) => s.get_ref().peer_addr(),
+            InnerNetworkStream::NativeTls(s) => s.get_ref().peer_addr(),
-            #[cfg(feature = "rustls-tls")]
+            #[cfg(feature = "rustls")]
-            InnerNetworkStream::RustlsTls(ref s) => s.get_ref().peer_addr(),
+            InnerNetworkStream::Rustls(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(
@@ -69,12 +75,14 @@ impl NetworkStream {
 
     /// Shutdowns the connection
     pub fn shutdown(&self, how: Shutdown) -> io::Result<()> {
-        match self.inner {
+        match &self.inner {
-            InnerNetworkStream::Tcp(ref s) => s.shutdown(how),
+            InnerNetworkStream::Tcp(s) => s.shutdown(how),
             #[cfg(feature = "native-tls")]
-            InnerNetworkStream::NativeTls(ref s) => s.get_ref().shutdown(how),
+            InnerNetworkStream::NativeTls(s) => s.get_ref().shutdown(how),
-            #[cfg(feature = "rustls-tls")]
+            #[cfg(feature = "rustls")]
-            InnerNetworkStream::RustlsTls(ref s) => s.get_ref().shutdown(how),
+            InnerNetworkStream::Rustls(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(())
@@ -86,20 +94,40 @@ 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().map_err(error::connection)?;
+            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 {
-                match TcpStream::connect_timeout(&addr, timeout) {
+                let socket = socket2::Socket::new(
-                    Ok(stream) => return Ok(stream),
+                    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(match last_err {
@@ -108,11 +136,7 @@ impl NetworkStream {
             })
         }
 
-        let tcp_stream = match timeout {
+        let tcp_stream = try_connect(server, timeout, local_addr)?;
-            Some(t) => try_connect_timeout(server, t)?,
-            None => TcpStream::connect(server).map_err(error::connection)?,
-        };
-
         let mut stream = NetworkStream::new(InnerNetworkStream::Tcp(tcp_stream));
         if let Some(tls_parameters) = tls_parameters {
             stream.upgrade_tls(tls_parameters)?;
@@ -122,19 +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 = mem::replace(&mut self.inner, InnerNetworkStream::None);
-                let tcp_stream = match tcp_stream {
+                let InnerNetworkStream::Tcp(tcp_stream) = tcp_stream else {
-                    InnerNetworkStream::Tcp(tcp_stream) => tcp_stream,
+                    unreachable!()
-                    _ => unreachable!(),
                 };
 
                 self.inner = Self::upgrade_tls_impl(tcp_stream, tls_parameters)?;
@@ -144,38 +167,53 @@ 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,
     ) -> Result<InnerNetworkStream, Error> {
-        Ok(match &tls_parameters.connector {
+        Ok(match &tls_parameters.inner {
             #[cfg(feature = "native-tls")]
-            InnerTlsParameters::NativeTls(connector) => {
+            InnerTlsParameters::NativeTls(inner) => {
-                let stream = connector
+                let stream = inner
-                    .connect(tls_parameters.domain(), tcp_stream)
+                    .connector
+                    .connect(&inner.server_name, tcp_stream)
                     .map_err(error::connection)?;
                 InnerNetworkStream::NativeTls(stream)
             }
-            #[cfg(feature = "rustls-tls")]
+            #[cfg(feature = "rustls")]
-            InnerTlsParameters::RustlsTls(connector) => {
+            InnerTlsParameters::Rustls(inner) => {
-                let domain = ServerName::try_from(tls_parameters.domain())
+                let connection = ClientConnection::new(
-                    .map_err(|_| error::connection("domain isn't a valid DNS name"))?;
+                    Arc::clone(&inner.connector),
-                let connection =
+                    inner.server_name.inner_ref().clone(),
-                    ClientConnection::new(connector.clone(), domain).map_err(error::connection)?;
+                )
+                .map_err(error::connection)?;
                 let stream = StreamOwned::new(connection, tcp_stream);
-                InnerNetworkStream::RustlsTls(stream)
+                InnerNetworkStream::Rustls(stream)
+            }
+            #[cfg(feature = "boring-tls")]
+            InnerTlsParameters::BoringTls(inner) => {
+                let stream = inner
+                    .connector
+                    .configure()
+                    .map_err(error::connection)?
+                    .verify_hostname(inner.extra_info.accept_invalid_hostnames)
+                    .connect(&inner.server_name, tcp_stream)
+                    .map_err(error::connection)?;
+                InnerNetworkStream::BoringTls(stream)
             }
         })
     }
 
     pub fn is_encrypted(&self) -> bool {
-        match self.inner {
+        match &self.inner {
             InnerNetworkStream::Tcp(_) => false,
             #[cfg(feature = "native-tls")]
             InnerNetworkStream::NativeTls(_) => true,
-            #[cfg(feature = "rustls-tls")]
+            #[cfg(feature = "rustls")]
-            InnerNetworkStream::RustlsTls(_) => true,
+            InnerNetworkStream::Rustls(_) => true,
+            #[cfg(feature = "boring-tls")]
+            InnerNetworkStream::BoringTls(_) => true,
             InnerNetworkStream::None => {
                 debug_assert!(false, "InnerNetworkStream::None must never be built");
                 false
@@ -183,17 +221,93 @@ impl NetworkStream {
         }
     }
 
-    pub fn set_read_timeout(&mut self, duration: Option<Duration>) -> io::Result<()> {
+    #[cfg(feature = "boring-tls")]
-        match self.inner {
+    #[cfg_attr(docsrs, doc(cfg(feature = "boring-tls")))]
-            InnerNetworkStream::Tcp(ref mut stream) => stream.set_read_timeout(duration),
+    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(ref mut stream) => {
+            InnerNetworkStream::NativeTls(_) => panic!("Unsupported"),
-                stream.get_ref().set_read_timeout(duration)
+            #[cfg(feature = "rustls")]
+            InnerNetworkStream::Rustls(_) => panic!("Unsupported"),
+            #[cfg(feature = "boring-tls")]
+            InnerNetworkStream::BoringTls(stream) => {
+                stream.ssl().verify_result().map_err(error::tls)
             }
-            #[cfg(feature = "rustls-tls")]
+            InnerNetworkStream::None => panic!("InnerNetworkStream::None must never be built"),
-            InnerNetworkStream::RustlsTls(ref mut stream) => {
-                stream.get_ref().set_read_timeout(duration)
         }
+    }
+
+    #[cfg(any(feature = "rustls", feature = "boring-tls"))]
+    #[cfg_attr(docsrs, doc(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::Rustls(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"))]
+    #[cfg_attr(
+        docsrs,
+        doc(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::Rustls(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 &mut self.inner {
+            InnerNetworkStream::Tcp(stream) => stream.set_read_timeout(duration),
+            #[cfg(feature = "native-tls")]
+            InnerNetworkStream::NativeTls(stream) => stream.get_ref().set_read_timeout(duration),
+            #[cfg(feature = "rustls")]
+            InnerNetworkStream::Rustls(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(())
@@ -203,18 +317,15 @@ impl NetworkStream {
 
     /// Set write timeout for IO calls
     pub fn set_write_timeout(&mut self, duration: Option<Duration>) -> io::Result<()> {
-        match self.inner {
+        match &mut self.inner {
-            InnerNetworkStream::Tcp(ref mut stream) => stream.set_write_timeout(duration),
+            InnerNetworkStream::Tcp(stream) => stream.set_write_timeout(duration),
 
             #[cfg(feature = "native-tls")]
-            InnerNetworkStream::NativeTls(ref mut stream) => {
+            InnerNetworkStream::NativeTls(stream) => stream.get_ref().set_write_timeout(duration),
-                stream.get_ref().set_write_timeout(duration)
+            #[cfg(feature = "rustls")]
-            }
+            InnerNetworkStream::Rustls(stream) => stream.get_ref().set_write_timeout(duration),
-            #[cfg(feature = "rustls-tls")]
+            #[cfg(feature = "boring-tls")]
-            InnerNetworkStream::RustlsTls(ref mut stream) => {
+            InnerNetworkStream::BoringTls(stream) => stream.get_ref().set_write_timeout(duration),
-                stream.get_ref().set_write_timeout(duration)
-            }
-
             InnerNetworkStream::None => {
                 debug_assert!(false, "InnerNetworkStream::None must never be built");
                 Ok(())
@@ -225,12 +336,14 @@ impl NetworkStream {
 
 impl Read for NetworkStream {
     fn read(&mut self, buf: &mut [u8]) -> io::Result<usize> {
-        match self.inner {
+        match &mut self.inner {
-            InnerNetworkStream::Tcp(ref mut s) => s.read(buf),
+            InnerNetworkStream::Tcp(s) => s.read(buf),
             #[cfg(feature = "native-tls")]
-            InnerNetworkStream::NativeTls(ref mut s) => s.read(buf),
+            InnerNetworkStream::NativeTls(s) => s.read(buf),
-            #[cfg(feature = "rustls-tls")]
+            #[cfg(feature = "rustls")]
-            InnerNetworkStream::RustlsTls(ref mut s) => s.read(buf),
+            InnerNetworkStream::Rustls(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)
@@ -241,12 +354,14 @@ impl Read for NetworkStream {
 
 impl Write for NetworkStream {
     fn write(&mut self, buf: &[u8]) -> io::Result<usize> {
-        match self.inner {
+        match &mut self.inner {
-            InnerNetworkStream::Tcp(ref mut s) => s.write(buf),
+            InnerNetworkStream::Tcp(s) => s.write(buf),
             #[cfg(feature = "native-tls")]
-            InnerNetworkStream::NativeTls(ref mut s) => s.write(buf),
+            InnerNetworkStream::NativeTls(s) => s.write(buf),
-            #[cfg(feature = "rustls-tls")]
+            #[cfg(feature = "rustls")]
-            InnerNetworkStream::RustlsTls(ref mut s) => s.write(buf),
+            InnerNetworkStream::Rustls(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)
@@ -255,12 +370,14 @@ impl Write for NetworkStream {
     }
 
     fn flush(&mut self) -> io::Result<()> {
-        match self.inner {
+        match &mut self.inner {
-            InnerNetworkStream::Tcp(ref mut s) => s.flush(),
+            InnerNetworkStream::Tcp(s) => s.flush(),
             #[cfg(feature = "native-tls")]
-            InnerNetworkStream::NativeTls(ref mut s) => s.flush(),
+            InnerNetworkStream::NativeTls(s) => s.flush(),
-            #[cfg(feature = "rustls-tls")]
+            #[cfg(feature = "rustls")]
-            InnerNetworkStream::RustlsTls(ref mut s) => s.flush(),
+            InnerNetworkStream::Rustls(s) => s.flush(),
+            #[cfg(feature = "boring-tls")]
+            InnerNetworkStream::BoringTls(s) => s.flush(),
             InnerNetworkStream::None => {
                 debug_assert!(false, "InnerNetworkStream::None must never be built");
                 Ok(())
@@ -268,3 +385,47 @@ impl Write for NetworkStream {
         }
     }
 }
+
+/// 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

@@ -1,316 +0,0 @@
-#[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
-use crate::transport::smtp::{error, Error};
-#[cfg(feature = "native-tls")]
-use native_tls::{Protocol, TlsConnector};
-#[cfg(feature = "rustls-tls")]
-use rustls::{
-    client::{ServerCertVerified, ServerCertVerifier, WebPkiVerifier},
-    ClientConfig, Error as TlsError, OwnedTrustAnchor, RootCertStore, ServerName,
-};
-use std::fmt::{self, Debug};
-#[cfg(feature = "rustls-tls")]
-use std::{sync::Arc, time::SystemTime};
-
-/// 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;
-
-/// How to apply TLS to a client connection
-#[derive(Clone)]
-#[allow(missing_copy_implementations)]
-pub enum Tls {
-    /// Insecure connection only (for testing purposes)
-    None,
-    /// Start with insecure connection and use `STARTTLS` when available
-    #[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
-    #[cfg_attr(docsrs, doc(cfg(any(feature = "native-tls", feature = "rustls-tls"))))]
-    Opportunistic(TlsParameters),
-    /// Start with insecure connection and require `STARTTLS`
-    #[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
-    #[cfg_attr(docsrs, doc(cfg(any(feature = "native-tls", feature = "rustls-tls"))))]
-    Required(TlsParameters),
-    /// Use TLS wrapped connection
-    #[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
-    #[cfg_attr(docsrs, doc(cfg(any(feature = "native-tls", feature = "rustls-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-tls"))]
-            Self::Opportunistic(_) => f.pad("Opportunistic"),
-            #[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
-            Self::Required(_) => f.pad("Required"),
-            #[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
-            Self::Wrapper(_) => f.pad("Wrapper"),
-        }
-    }
-}
-
-/// Parameters to use for secure clients
-#[derive(Clone)]
-pub struct TlsParameters {
-    pub(crate) connector: InnerTlsParameters,
-    /// The domain name which is expected in the TLS certificate from the server
-    pub(super) domain: String,
-}
-
-/// Builder for `TlsParameters`
-#[derive(Debug, Clone)]
-pub struct TlsParametersBuilder {
-    domain: String,
-    root_certs: Vec<Certificate>,
-    accept_invalid_hostnames: bool,
-    accept_invalid_certs: bool,
-}
-
-impl TlsParametersBuilder {
-    /// Creates a new builder for `TlsParameters`
-    pub fn new(domain: String) -> Self {
-        Self {
-            domain,
-            root_certs: Vec::new(),
-            accept_invalid_hostnames: false,
-            accept_invalid_certs: false,
-        }
-    }
-
-    /// 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) -> Self {
-        self.root_certs.push(cert);
-        self
-    }
-
-    /// Controls whether certificates with an invalid hostname are accepted
-    ///
-    /// Defaults to `false`.
-    ///
-    /// # Warning
-    ///
-    /// You should think very carefully before using this method.
-    /// If hostname verification is disabled *any* valid certificate,
-    /// 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) -> Self {
-        self.accept_invalid_hostnames = accept_invalid_hostnames;
-        self
-    }
-
-    /// Controls whether invalid certificates are accepted
-    ///
-    /// Defaults to `false`.
-    ///
-    /// # Warning
-    ///
-    /// You should think very carefully before using this method.
-    /// If certificate verification is disabled, *any* certificate
-    /// is trusted for use, including:
-    ///
-    /// * Self signed certificates
-    /// * Certificates from different hostnames
-    /// * Expired certificates
-    ///
-    /// 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) -> Self {
-        self.accept_invalid_certs = accept_invalid_certs;
-        self
-    }
-
-    /// 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"))))]
-    pub fn build(self) -> Result<TlsParameters, Error> {
-        #[cfg(feature = "rustls-tls")]
-        return self.build_rustls();
-
-        #[cfg(not(feature = "rustls-tls"))]
-        return self.build_native();
-    }
-
-    /// Creates a new `TlsParameters` using native-tls with the provided configuration
-    #[cfg(feature = "native-tls")]
-    #[cfg_attr(docsrs, doc(cfg(feature = "native-tls")))]
-    pub fn build_native(self) -> Result<TlsParameters, Error> {
-        let mut tls_builder = TlsConnector::builder();
-
-        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().map_err(error::tls)?;
-        Ok(TlsParameters {
-            connector: InnerTlsParameters::NativeTls(connector),
-            domain: self.domain,
-        })
-    }
-
-    /// Creates a new `TlsParameters` using rustls with the provided configuration
-    #[cfg(feature = "rustls-tls")]
-    #[cfg_attr(docsrs, doc(cfg(feature = "rustls-tls")))]
-    pub fn build_rustls(self) -> Result<TlsParameters, Error> {
-        let tls = ClientConfig::builder();
-        let tls = tls.with_safe_defaults();
-
-        let tls = if self.accept_invalid_certs {
-            tls.with_custom_certificate_verifier(Arc::new(InvalidCertsVerifier {}))
-        } else {
-            let mut root_cert_store = RootCertStore::empty();
-            for cert in self.root_certs {
-                for rustls_cert in cert.rustls {
-                    root_cert_store.add(&rustls_cert).map_err(error::tls)?;
-                }
-            }
-            root_cert_store.add_server_trust_anchors(webpki_roots::TLS_SERVER_ROOTS.0.iter().map(
-                |ta| {
-                    OwnedTrustAnchor::from_subject_spki_name_constraints(
-                        ta.subject,
-                        ta.spki,
-                        ta.name_constraints,
-                    )
-                },
-            ));
-
-            tls.with_custom_certificate_verifier(Arc::new(WebPkiVerifier::new(
-                root_cert_store,
-                None,
-            )))
-        };
-        let tls = tls.with_no_client_auth();
-
-        Ok(TlsParameters {
-            connector: InnerTlsParameters::RustlsTls(Arc::new(tls)),
-            domain: self.domain,
-        })
-    }
-}
-
-#[derive(Clone)]
-pub enum InnerTlsParameters {
-    #[cfg(feature = "native-tls")]
-    NativeTls(TlsConnector),
-    #[cfg(feature = "rustls-tls")]
-    RustlsTls(Arc<ClientConfig>),
-}
-
-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"))))]
-    pub fn new(domain: String) -> Result<Self, Error> {
-        TlsParametersBuilder::new(domain).build()
-    }
-
-    pub fn builder(domain: String) -> TlsParametersBuilder {
-        TlsParametersBuilder::new(domain)
-    }
-
-    /// Creates a new `TlsParameters` using native-tls
-    #[cfg(feature = "native-tls")]
-    #[cfg_attr(docsrs, doc(cfg(feature = "native-tls")))]
-    pub fn new_native(domain: String) -> Result<Self, Error> {
-        TlsParametersBuilder::new(domain).build_native()
-    }
-
-    /// Creates a new `TlsParameters` using rustls
-    #[cfg(feature = "rustls-tls")]
-    #[cfg_attr(docsrs, doc(cfg(feature = "rustls-tls")))]
-    pub fn new_rustls(domain: String) -> Result<Self, Error> {
-        TlsParametersBuilder::new(domain).build_rustls()
-    }
-
-    pub fn domain(&self) -> &str {
-        &self.domain
-    }
-}
-
-/// A client 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(any(feature = "native-tls", feature = "rustls-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::tls)?;
-
-        Ok(Self {
-            #[cfg(feature = "native-tls")]
-            native_tls: native_tls_cert,
-            #[cfg(feature = "rustls-tls")]
-            rustls: vec![rustls::Certificate(der)],
-        })
-    }
-
-    /// 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::tls)?;
-
-        #[cfg(feature = "rustls-tls")]
-        let rustls_cert = {
-            use std::io::Cursor;
-
-            let mut pem = Cursor::new(pem);
-            rustls_pemfile::certs(&mut pem)
-                .map_err(|_| error::tls("invalid certificates"))?
-                .into_iter()
-                .map(rustls::Certificate)
-                .collect::<Vec<_>>()
-        };
-
-        Ok(Self {
-            #[cfg(feature = "native-tls")]
-            native_tls: native_tls_cert,
-            #[cfg(feature = "rustls-tls")]
-            rustls: rustls_cert,
-        })
-    }
-}
-
-impl Debug for Certificate {
-    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
-        f.debug_struct("Certificate").finish()
-    }
-}
-
-#[cfg(feature = "rustls-tls")]
-struct InvalidCertsVerifier;
-
-#[cfg(feature = "rustls-tls")]
-impl ServerCertVerifier for InvalidCertsVerifier {
-    fn verify_server_cert(
-        &self,
-        _end_entity: &rustls::Certificate,
-        _intermediates: &[rustls::Certificate],
-        _server_name: &ServerName,
-        _scts: &mut dyn Iterator<Item = &[u8]>,
-        _ocsp_response: &[u8],
-        _now: SystemTime,
-    ) -> Result<ServerCertVerified, TlsError> {
-        Ok(ServerCertVerified::assertion())
-    }
-}

src/transport/smtp/client/tls/boring_tls.rs

@@ -0,0 +1,111 @@
+use std::fmt::{self, Debug};
+
+use boring::{
+    ssl::{SslConnector, SslMethod, SslVerifyMode, SslVersion},
+    x509::store::X509StoreBuilder,
+};
+
+use crate::transport::smtp::error::{self, Error};
+
+pub(super) fn build_connector(
+    builder: super::TlsParametersBuilder<super::BoringTls>,
+) -> Result<(Box<str>, SslConnector), Error> {
+    let mut tls_builder = SslConnector::builder(SslMethod::tls_client()).map_err(error::tls)?;
+
+    if builder.accept_invalid_certs {
+        tls_builder.set_verify(SslVerifyMode::NONE);
+    } else {
+        match builder.cert_store {
+            CertificateStore::System => {}
+            CertificateStore::None => {
+                // Replace the default store with an empty store.
+                tls_builder.set_cert_store(X509StoreBuilder::new().map_err(error::tls)?.build());
+            }
+        }
+
+        let cert_store = tls_builder.cert_store_mut();
+
+        for cert in builder.root_certs {
+            cert_store.add_cert(cert.0).map_err(error::tls)?;
+        }
+    }
+
+    if let Some(identity) = builder.identity {
+        tls_builder
+            .set_certificate(identity.chain.as_ref())
+            .map_err(error::tls)?;
+        tls_builder
+            .set_private_key(identity.key.as_ref())
+            .map_err(error::tls)?;
+    }
+
+    let min_tls_version = match builder.min_tls_version {
+        MinTlsVersion::Tlsv10 => SslVersion::TLS1,
+        MinTlsVersion::Tlsv11 => SslVersion::TLS1_1,
+        MinTlsVersion::Tlsv12 => SslVersion::TLS1_2,
+        MinTlsVersion::Tlsv13 => SslVersion::TLS1_3,
+    };
+
+    tls_builder
+        .set_min_proto_version(Some(min_tls_version))
+        .map_err(error::tls)?;
+    Ok((builder.server_name.into_boxed_str(), tls_builder.build()))
+}
+
+#[derive(Debug, Clone, Default)]
+#[allow(missing_copy_implementations)]
+#[non_exhaustive]
+pub(super) enum CertificateStore {
+    #[default]
+    System,
+    None,
+}
+
+#[derive(Clone)]
+pub(super) struct Certificate(pub(super) boring::x509::X509);
+
+impl Certificate {
+    pub(super) fn from_pem(pem: &[u8]) -> Result<Self, Error> {
+        Ok(Self(boring::x509::X509::from_pem(pem).map_err(error::tls)?))
+    }
+
+    pub(super) fn from_der(der: &[u8]) -> Result<Self, Error> {
+        Ok(Self(boring::x509::X509::from_der(der).map_err(error::tls)?))
+    }
+}
+
+impl Debug for Certificate {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        f.debug_struct("Certificate").finish_non_exhaustive()
+    }
+}
+
+#[derive(Clone)]
+pub(super) struct Identity {
+    pub(super) chain: boring::x509::X509,
+    pub(super) key: boring::pkey::PKey<boring::pkey::Private>,
+}
+
+impl Identity {
+    pub(super) fn from_pem(pem: &[u8], key: &[u8]) -> Result<Self, Error> {
+        let chain = 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(Self { chain, key })
+    }
+}
+
+impl Debug for Identity {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        f.debug_struct("Identity").finish_non_exhaustive()
+    }
+}
+
+#[derive(Debug, Copy, Clone, Default)]
+#[non_exhaustive]
+pub(super) enum MinTlsVersion {
+    Tlsv10,
+    Tlsv11,
+    #[default]
+    Tlsv12,
+    Tlsv13,
+}

src/transport/smtp/client/tls/current.rs

@@ -0,0 +1,601 @@
+use std::fmt::{self, Debug};
+
+use super::TlsBackend;
+#[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+use crate::transport::smtp::error;
+use crate::transport::smtp::Error;
+
+/// 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,
+}
+
+/// 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)]
+#[cfg_attr(
+    not(any(feature = "native-tls", feature = "rustls", feature = "boring-tls")),
+    deprecated(
+        note = "starting from lettre v0.12 `Tls` won't be available when none of the TLS backends are enabled"
+    )
+)]
+#[cfg_attr(
+    docsrs,
+    doc(cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls")))
+)]
+pub enum Tls {
+    /// 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,
+    /// 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),
+    /// 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),
+    /// 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)]
+#[cfg_attr(
+    not(any(feature = "native-tls", feature = "rustls", feature = "boring-tls")),
+    deprecated(
+        note = "starting from lettre v0.12 `CertificateStore` won't be available when none of the TLS backends are enabled"
+    )
+)]
+#[cfg_attr(
+    docsrs,
+    doc(cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls")))
+)]
+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 use the system certificate verifier if the `rustls-platform-verifier`
+    /// feature is enabled. If the `rustls-native-certs` feature is enabled, system certificate
+    /// store will be used. Otherwise, it 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)]
+#[cfg_attr(
+    not(any(feature = "native-tls", feature = "rustls", feature = "boring-tls")),
+    deprecated(
+        note = "starting from lettre v0.12 `TlsParameters` won't be available when none of the TLS backends are enabled"
+    )
+)]
+#[cfg_attr(
+    docsrs,
+    doc(cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls")))
+)]
+pub struct TlsParameters {
+    pub(in crate::transport::smtp) inner: InnerTlsParameters,
+}
+
+/// Builder for `TlsParameters`
+#[derive(Debug, Clone)]
+#[cfg_attr(
+    not(any(feature = "native-tls", feature = "rustls", feature = "boring-tls")),
+    deprecated(
+        note = "starting from lettre v0.12 `TlsParametersBuilder` won't be available when none of the TLS backends are enabled"
+    )
+)]
+#[cfg_attr(
+    docsrs,
+    doc(cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls")))
+)]
+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 {
+    /// Creates a new builder for `TlsParameters`
+    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) -> 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
+    ///
+    /// This option is silently disabled when using `rustls-platform-verifier`.
+    ///
+    /// Defaults to `false`.
+    ///
+    /// # Warning
+    ///
+    /// You should think very carefully before using this method.
+    /// If hostname verification is disabled *any* valid certificate,
+    /// including those from other sites, are trusted.
+    ///
+    /// This method introduces significant vulnerabilities to man-in-the-middle attacks.
+    #[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"))]
+    #[cfg_attr(
+        docsrs,
+        doc(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`.
+    ///
+    /// # Warning
+    ///
+    /// You should think very carefully before using this method.
+    /// If certificate verification is disabled, *any* certificate
+    /// is trusted for use, including:
+    ///
+    /// * Self signed certificates
+    /// * Certificates from different hostnames
+    /// * Expired certificates
+    ///
+    /// 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) -> Self {
+        self.accept_invalid_certs = accept_invalid_certs;
+        self
+    }
+
+    /// Creates a new `TlsParameters` using native-tls, boring-tls or rustls
+    /// depending on which one is available
+    #[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> {
+        #[cfg(feature = "rustls")]
+        return self.build_rustls();
+        #[cfg(all(not(feature = "rustls"), feature = "native-tls"))]
+        return self.build_native();
+        #[cfg(all(not(feature = "rustls"), feature = "boring-tls"))]
+        return self.build_boring();
+    }
+
+    /// Creates a new `TlsParameters` using native-tls with the provided configuration
+    #[cfg(feature = "native-tls")]
+    #[cfg_attr(docsrs, doc(cfg(feature = "native-tls")))]
+    pub fn build_native(self) -> Result<TlsParameters, Error> {
+        let cert_store = match self.cert_store {
+            CertificateStore::Default => super::native_tls::CertificateStore::System,
+            CertificateStore::None => super::native_tls::CertificateStore::None,
+            #[allow(unreachable_patterns)]
+            other => {
+                return Err(error::tls(format!(
+                    "{other:?} is not supported in native tls"
+                )))
+            }
+        };
+        let min_tls_version = match self.min_tls_version {
+            TlsVersion::Tlsv10 => super::native_tls::MinTlsVersion::Tlsv10,
+            TlsVersion::Tlsv11 => super::native_tls::MinTlsVersion::Tlsv11,
+            TlsVersion::Tlsv12 => super::native_tls::MinTlsVersion::Tlsv12,
+            TlsVersion::Tlsv13 => {
+                return Err(error::tls(
+                    "min tls version Tlsv13 not supported in native tls",
+                ))
+            }
+        };
+
+        let mut builder = super::TlsParametersBuilder::<super::NativeTls>::new(self.domain)
+            .certificate_store(cert_store)
+            .dangerous_accept_invalid_certs(self.accept_invalid_certs)
+            .dangerous_accept_invalid_hostnames(self.accept_invalid_hostnames)
+            .min_tls_version(min_tls_version);
+        for cert in self.root_certs {
+            builder = builder.add_root_certificate(cert.native_tls);
+        }
+        if let Some(identity) = self.identity {
+            builder = builder.identify_with(identity.native_tls);
+        }
+
+        builder
+            .build()
+            .map(super::NativeTls::__build_current_tls_parameters)
+    }
+
+    /// Creates a new `TlsParameters` using boring-tls with the provided configuration
+    ///
+    /// Warning: this uses the certificate store passed via `certificate_store`
+    /// instead of the one configured in [`TlsParametersBuilder::certificate_store`].
+    #[cfg(feature = "boring-tls")]
+    #[cfg_attr(docsrs, doc(cfg(feature = "boring-tls")))]
+    pub fn build_boring(self) -> Result<TlsParameters, Error> {
+        let cert_store = match self.cert_store {
+            CertificateStore::Default => super::boring_tls::CertificateStore::System,
+            CertificateStore::None => super::boring_tls::CertificateStore::None,
+            #[allow(unreachable_patterns)]
+            other => {
+                return Err(error::tls(format!(
+                    "{other:?} is not supported in native tls"
+                )))
+            }
+        };
+        let min_tls_version = match self.min_tls_version {
+            TlsVersion::Tlsv10 => super::boring_tls::MinTlsVersion::Tlsv10,
+            TlsVersion::Tlsv11 => super::boring_tls::MinTlsVersion::Tlsv11,
+            TlsVersion::Tlsv12 => super::boring_tls::MinTlsVersion::Tlsv12,
+            TlsVersion::Tlsv13 => super::boring_tls::MinTlsVersion::Tlsv13,
+        };
+
+        let mut builder = super::TlsParametersBuilder::<super::BoringTls>::new(self.domain)
+            .certificate_store(cert_store)
+            .dangerous_accept_invalid_certs(self.accept_invalid_certs)
+            .dangerous_accept_invalid_hostnames(self.accept_invalid_hostnames)
+            .min_tls_version(min_tls_version);
+        for cert in self.root_certs {
+            builder = builder.add_root_certificate(cert.boring_tls);
+        }
+        if let Some(identity) = self.identity {
+            builder = builder.identify_with(identity.boring_tls);
+        }
+
+        builder
+            .build()
+            .map(super::BoringTls::__build_current_tls_parameters)
+    }
+
+    /// Creates a new `TlsParameters` using rustls with the provided configuration
+    #[cfg(feature = "rustls")]
+    #[cfg_attr(docsrs, doc(cfg(feature = "rustls")))]
+    pub fn build_rustls(self) -> Result<TlsParameters, Error> {
+        let cert_store = match self.cert_store {
+            CertificateStore::Default => super::rustls::CertificateStore::default(),
+            #[cfg(feature = "webpki-roots")]
+            CertificateStore::WebpkiRoots => super::rustls::CertificateStore::WebpkiRoots,
+            CertificateStore::None => super::rustls::CertificateStore::None,
+        };
+        let min_tls_version = 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 => super::rustls::MinTlsVersion::Tlsv12,
+            TlsVersion::Tlsv13 => super::rustls::MinTlsVersion::Tlsv13,
+        };
+
+        let mut builder = super::TlsParametersBuilder::<super::Rustls>::new(self.domain)
+            .certificate_store(cert_store)
+            .dangerous_accept_invalid_certs(self.accept_invalid_certs)
+            .dangerous_accept_invalid_hostnames(self.accept_invalid_hostnames)
+            .min_tls_version(min_tls_version);
+        for cert in self.root_certs {
+            for cert in cert.rustls {
+                builder = builder.add_root_certificate(cert);
+            }
+        }
+        if let Some(identity) = self.identity {
+            builder = builder.identify_with(identity.rustls_tls);
+        }
+
+        builder
+            .build()
+            .map(super::Rustls::__build_current_tls_parameters)
+    }
+}
+
+#[derive(Clone)]
+#[allow(clippy::enum_variant_names)]
+pub(in crate::transport::smtp) enum InnerTlsParameters {
+    #[cfg(feature = "native-tls")]
+    NativeTls(super::TlsParameters<super::NativeTls>),
+    #[cfg(feature = "rustls")]
+    Rustls(super::TlsParameters<super::Rustls>),
+    #[cfg(feature = "boring-tls")]
+    BoringTls(super::TlsParameters<super::BoringTls>),
+}
+
+impl TlsParameters {
+    /// Creates a new `TlsParameters` using native-tls or rustls
+    /// depending on which one is available
+    #[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> {
+        Self::new_with::<super::DefaultTlsBackend>(domain)
+    }
+
+    /// Creates a new `TlsParameters` builder
+    pub fn builder(domain: String) -> TlsParametersBuilder {
+        TlsParametersBuilder::new(domain)
+    }
+
+    /// Creates a new `TlsParameters` using native-tls
+    #[cfg(feature = "native-tls")]
+    #[cfg_attr(docsrs, doc(cfg(feature = "native-tls")))]
+    pub fn new_native(domain: String) -> Result<Self, Error> {
+        Self::new_with::<super::NativeTls>(domain)
+    }
+
+    /// Creates a new `TlsParameters` using rustls
+    #[cfg(feature = "rustls")]
+    #[cfg_attr(docsrs, doc(cfg(feature = "rustls")))]
+    pub fn new_rustls(domain: String) -> Result<Self, Error> {
+        Self::new_with::<super::Rustls>(domain)
+    }
+
+    /// 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> {
+        Self::new_with::<super::BoringTls>(domain)
+    }
+
+    fn new_with<B: TlsBackend>(domain: String) -> Result<Self, Error> {
+        super::TlsParametersBuilder::<B>::new(domain)
+            .build()
+            .map(B::__build_current_tls_parameters)
+    }
+
+    pub fn domain(&self) -> &str {
+        match self.inner {
+            #[cfg(feature = "native-tls")]
+            InnerTlsParameters::NativeTls(ref inner) => &inner.server_name,
+            #[cfg(feature = "rustls")]
+            InnerTlsParameters::Rustls(ref inner) => inner.server_name.as_ref(),
+            #[cfg(feature = "boring-tls")]
+            InnerTlsParameters::BoringTls(ref inner) => &inner.server_name,
+        }
+    }
+}
+
+/// A certificate that can be used with [`TlsParametersBuilder::add_root_certificate`]
+#[derive(Clone)]
+#[allow(missing_copy_implementations)]
+#[cfg_attr(
+    not(any(feature = "native-tls", feature = "rustls", feature = "boring-tls")),
+    deprecated(
+        note = "starting from lettre v0.12 `Certificate` won't be available when none of the TLS backends are enabled"
+    )
+)]
+#[cfg_attr(
+    docsrs,
+    doc(cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls")))
+)]
+pub struct Certificate {
+    #[cfg(feature = "native-tls")]
+    native_tls: super::native_tls::Certificate,
+    #[cfg(feature = "rustls")]
+    rustls: Vec<super::rustls::Certificate>,
+    #[cfg(feature = "boring-tls")]
+    boring_tls: super::boring_tls::Certificate,
+}
+
+#[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> {
+        Ok(Self {
+            #[cfg(feature = "native-tls")]
+            native_tls: super::native_tls::Certificate::from_der(&der)?,
+            #[cfg(feature = "boring-tls")]
+            boring_tls: super::boring_tls::Certificate::from_der(&der)?,
+            #[cfg(feature = "rustls")]
+            rustls: vec![super::rustls::Certificate::from_der(der)],
+        })
+    }
+
+    /// Create a `Certificate` from a PEM encoded certificate
+    pub fn from_pem(pem: &[u8]) -> Result<Self, Error> {
+        Ok(Self {
+            #[cfg(feature = "native-tls")]
+            native_tls: super::native_tls::Certificate::from_pem(pem)?,
+            #[cfg(feature = "rustls")]
+            rustls: super::rustls::Certificate::from_pem_bundle(pem)?,
+            #[cfg(feature = "boring-tls")]
+            boring_tls: super::boring_tls::Certificate::from_pem(pem)?,
+        })
+    }
+}
+
+impl Debug for Certificate {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        f.debug_struct("Certificate").finish()
+    }
+}
+
+/// An identity that can be used with [`TlsParametersBuilder::identify_with`]
+#[derive(Clone)]
+#[allow(missing_copy_implementations)]
+#[cfg_attr(
+    not(any(feature = "native-tls", feature = "rustls", feature = "boring-tls")),
+    deprecated(
+        note = "starting from lettre v0.12 `Identity` won't be available when none of the TLS backends are enabled"
+    )
+)]
+#[cfg_attr(
+    docsrs,
+    doc(cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls")))
+)]
+pub struct Identity {
+    #[cfg(feature = "native-tls")]
+    native_tls: super::native_tls::Identity,
+    #[cfg(feature = "rustls")]
+    rustls_tls: super::rustls::Identity,
+    #[cfg(feature = "boring-tls")]
+    boring_tls: super::boring_tls::Identity,
+}
+
+impl Debug for Identity {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        f.debug_struct("Identity").finish()
+    }
+}
+
+#[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: super::native_tls::Identity::from_pem(pem, key)?,
+            #[cfg(feature = "rustls")]
+            rustls_tls: super::rustls::Identity::from_pem(pem, key)?,
+            #[cfg(feature = "boring-tls")]
+            boring_tls: super::boring_tls::Identity::from_pem(pem, key)?,
+        })
+    }
+}

src/transport/smtp/client/tls/mod.rs

@@ -0,0 +1,253 @@
+use crate::transport::smtp::Error;
+
+#[cfg(feature = "boring-tls")]
+#[cfg_attr(docsrs, doc(cfg(feature = "boring-tls")))]
+pub(super) mod boring_tls;
+pub(super) mod current;
+#[cfg(feature = "native-tls")]
+#[cfg_attr(docsrs, doc(cfg(feature = "native-tls")))]
+pub(super) mod native_tls;
+#[cfg(feature = "rustls")]
+#[cfg_attr(docsrs, doc(cfg(feature = "rustls")))]
+pub(super) mod rustls;
+
+#[derive(Debug)]
+#[allow(private_bounds)]
+pub(in crate::transport::smtp) struct TlsParameters<B: TlsBackend> {
+    pub(in crate::transport::smtp) server_name: B::ServerName,
+    pub(in crate::transport::smtp) connector: B::Connector,
+    pub(in crate::transport::smtp) extra_info: B::ExtraInfo,
+}
+
+impl<B: TlsBackend> Clone for TlsParameters<B> {
+    fn clone(&self) -> Self {
+        Self {
+            server_name: self.server_name.clone(),
+            connector: self.connector.clone(),
+            extra_info: self.extra_info.clone(),
+        }
+    }
+}
+
+#[derive(Debug)]
+struct TlsParametersBuilder<B: TlsBackend> {
+    server_name: String,
+    cert_store: B::CertificateStore,
+    root_certs: Vec<B::Certificate>,
+    identity: Option<B::Identity>,
+    accept_invalid_certs: bool,
+    accept_invalid_hostnames: bool,
+    min_tls_version: B::MinTlsVersion,
+}
+
+impl<B: TlsBackend> TlsParametersBuilder<B> {
+    fn new(server_name: String) -> Self {
+        Self {
+            server_name,
+            cert_store: Default::default(),
+            root_certs: Vec::new(),
+            identity: None,
+            accept_invalid_certs: false,
+            accept_invalid_hostnames: false,
+            min_tls_version: Default::default(),
+        }
+    }
+
+    fn certificate_store(mut self, cert_store: B::CertificateStore) -> Self {
+        self.cert_store = cert_store;
+        self
+    }
+
+    fn add_root_certificate(mut self, cert: B::Certificate) -> Self {
+        self.root_certs.push(cert);
+        self
+    }
+
+    fn identify_with(mut self, identity: B::Identity) -> Self {
+        self.identity = Some(identity);
+        self
+    }
+
+    fn min_tls_version(mut self, min_tls_version: B::MinTlsVersion) -> Self {
+        self.min_tls_version = min_tls_version;
+        self
+    }
+
+    fn dangerous_accept_invalid_certs(mut self, accept_invalid_certs: bool) -> Self {
+        self.accept_invalid_certs = accept_invalid_certs;
+        self
+    }
+
+    fn dangerous_accept_invalid_hostnames(mut self, accept_invalid_hostnames: bool) -> Self {
+        self.accept_invalid_hostnames = accept_invalid_hostnames;
+        self
+    }
+
+    fn build(self) -> Result<TlsParameters<B>, Error> {
+        B::__build_connector(self)
+    }
+}
+
+#[allow(private_bounds)]
+trait TlsBackend: private::SealedTlsBackend {
+    type CertificateStore: Default;
+    type Certificate;
+    type Identity;
+    type MinTlsVersion: Default;
+
+    #[doc(hidden)]
+    fn __build_connector(builder: TlsParametersBuilder<Self>)
+        -> Result<TlsParameters<Self>, Error>;
+
+    #[doc(hidden)]
+    fn __build_current_tls_parameters(inner: TlsParameters<Self>) -> self::current::TlsParameters;
+}
+
+#[cfg(feature = "native-tls")]
+type DefaultTlsBackend = NativeTls;
+
+#[cfg(all(feature = "rustls", not(feature = "native-tls")))]
+type DefaultTlsBackend = Rustls;
+
+#[cfg(all(
+    feature = "boring-tls",
+    not(feature = "native-tls"),
+    not(feature = "rustls")
+))]
+type DefaultTlsBackend = BoringTls;
+
+#[cfg(feature = "native-tls")]
+#[cfg_attr(docsrs, doc(cfg(feature = "native-tls")))]
+#[derive(Debug)]
+#[allow(missing_copy_implementations)]
+#[non_exhaustive]
+pub(in crate::transport::smtp) struct NativeTls;
+
+#[cfg(feature = "native-tls")]
+#[cfg_attr(docsrs, doc(cfg(feature = "native-tls")))]
+impl TlsBackend for NativeTls {
+    type CertificateStore = self::native_tls::CertificateStore;
+    type Certificate = self::native_tls::Certificate;
+    type Identity = self::native_tls::Identity;
+    type MinTlsVersion = self::native_tls::MinTlsVersion;
+
+    fn __build_connector(
+        builder: TlsParametersBuilder<Self>,
+    ) -> Result<TlsParameters<Self>, Error> {
+        self::native_tls::build_connector(builder).map(|(server_name, connector)| TlsParameters {
+            server_name,
+            connector,
+            extra_info: (),
+        })
+    }
+
+    fn __build_current_tls_parameters(inner: TlsParameters<Self>) -> self::current::TlsParameters {
+        self::current::TlsParameters {
+            inner: self::current::InnerTlsParameters::NativeTls(inner),
+        }
+    }
+}
+
+#[cfg(feature = "rustls")]
+#[cfg_attr(docsrs, doc(cfg(feature = "rustls")))]
+#[derive(Debug)]
+#[allow(missing_copy_implementations)]
+#[non_exhaustive]
+pub(in crate::transport::smtp) struct Rustls;
+
+#[cfg(feature = "rustls")]
+#[cfg_attr(docsrs, doc(cfg(feature = "rustls")))]
+impl TlsBackend for Rustls {
+    type CertificateStore = self::rustls::CertificateStore;
+    type Certificate = self::rustls::Certificate;
+    type Identity = self::rustls::Identity;
+    type MinTlsVersion = self::rustls::MinTlsVersion;
+
+    fn __build_connector(
+        builder: TlsParametersBuilder<Self>,
+    ) -> Result<TlsParameters<Self>, Error> {
+        self::rustls::build_connector(builder).map(|(server_name, connector)| TlsParameters {
+            server_name,
+            connector,
+            extra_info: (),
+        })
+    }
+
+    fn __build_current_tls_parameters(inner: TlsParameters<Self>) -> self::current::TlsParameters {
+        self::current::TlsParameters {
+            inner: self::current::InnerTlsParameters::Rustls(inner),
+        }
+    }
+}
+
+#[cfg(feature = "boring-tls")]
+#[cfg_attr(docsrs, doc(cfg(feature = "boring-tls")))]
+#[derive(Debug)]
+#[allow(missing_copy_implementations)]
+#[non_exhaustive]
+pub(in crate::transport::smtp) struct BoringTls;
+
+#[cfg(feature = "boring-tls")]
+#[cfg_attr(docsrs, doc(cfg(feature = "boring-tls")))]
+impl TlsBackend for BoringTls {
+    type CertificateStore = self::boring_tls::CertificateStore;
+    type Certificate = self::boring_tls::Certificate;
+    type Identity = self::boring_tls::Identity;
+    type MinTlsVersion = self::boring_tls::MinTlsVersion;
+
+    fn __build_connector(
+        builder: TlsParametersBuilder<Self>,
+    ) -> Result<TlsParameters<Self>, Error> {
+        let accept_invalid_hostnames = builder.accept_invalid_hostnames;
+        self::boring_tls::build_connector(builder).map(|(server_name, connector)| TlsParameters {
+            server_name,
+            connector,
+            extra_info: BoringTlsExtraInfo {
+                accept_invalid_hostnames,
+            },
+        })
+    }
+
+    fn __build_current_tls_parameters(inner: TlsParameters<Self>) -> self::current::TlsParameters {
+        self::current::TlsParameters {
+            inner: self::current::InnerTlsParameters::BoringTls(inner),
+        }
+    }
+}
+
+#[cfg(feature = "boring-tls")]
+#[derive(Debug, Clone)]
+pub(in crate::transport::smtp) struct BoringTlsExtraInfo {
+    pub(super) accept_invalid_hostnames: bool,
+}
+
+mod private {
+    pub(in crate::transport::smtp) trait SealedTlsBackend:
+        Sized
+    {
+        type ServerName: Clone + AsRef<str>;
+        type Connector: Clone;
+        type ExtraInfo: Clone;
+    }
+
+    #[cfg(feature = "native-tls")]
+    impl SealedTlsBackend for super::NativeTls {
+        type ServerName = Box<str>;
+        type Connector = native_tls::TlsConnector;
+        type ExtraInfo = ();
+    }
+
+    #[cfg(feature = "rustls")]
+    impl SealedTlsBackend for super::Rustls {
+        type ServerName = super::rustls::ServerName;
+        type Connector = std::sync::Arc<rustls::client::ClientConfig>;
+        type ExtraInfo = ();
+    }
+
+    #[cfg(feature = "boring-tls")]
+    impl SealedTlsBackend for super::BoringTls {
+        type ServerName = Box<str>;
+        type Connector = boring::ssl::SslConnector;
+        type ExtraInfo = super::BoringTlsExtraInfo;
+    }
+}

src/transport/smtp/client/tls/native_tls.rs

@@ -0,0 +1,95 @@
+use std::fmt::{self, Debug};
+
+use native_tls::TlsConnector;
+
+use crate::transport::smtp::error::{self, Error};
+
+pub(super) fn build_connector(
+    builder: super::TlsParametersBuilder<super::NativeTls>,
+) -> Result<(Box<str>, TlsConnector), Error> {
+    let mut tls_builder = TlsConnector::builder();
+
+    match builder.cert_store {
+        CertificateStore::System => {}
+        CertificateStore::None => {
+            tls_builder.disable_built_in_roots(true);
+        }
+    }
+    for cert in builder.root_certs {
+        tls_builder.add_root_certificate(cert.0);
+    }
+    tls_builder.danger_accept_invalid_hostnames(builder.accept_invalid_hostnames);
+    tls_builder.danger_accept_invalid_certs(builder.accept_invalid_certs);
+
+    let min_tls_version = match builder.min_tls_version {
+        MinTlsVersion::Tlsv10 => native_tls::Protocol::Tlsv10,
+        MinTlsVersion::Tlsv11 => native_tls::Protocol::Tlsv11,
+        MinTlsVersion::Tlsv12 => native_tls::Protocol::Tlsv12,
+    };
+
+    tls_builder.min_protocol_version(Some(min_tls_version));
+    if let Some(identity) = builder.identity {
+        tls_builder.identity(identity.0);
+    }
+
+    let connector = tls_builder.build().map_err(error::tls)?;
+    Ok((builder.server_name.into_boxed_str(), connector))
+}
+
+#[derive(Debug, Clone, Default)]
+#[allow(missing_copy_implementations)]
+#[non_exhaustive]
+pub(super) enum CertificateStore {
+    #[default]
+    System,
+    None,
+}
+
+#[derive(Clone)]
+pub(super) struct Certificate(pub(super) native_tls::Certificate);
+
+impl Certificate {
+    pub(super) fn from_pem(pem: &[u8]) -> Result<Self, Error> {
+        Ok(Self(
+            native_tls::Certificate::from_pem(pem).map_err(error::tls)?,
+        ))
+    }
+
+    pub(super) fn from_der(der: &[u8]) -> Result<Self, Error> {
+        Ok(Self(
+            native_tls::Certificate::from_der(der).map_err(error::tls)?,
+        ))
+    }
+}
+
+impl Debug for Certificate {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        f.debug_struct("Certificate").finish_non_exhaustive()
+    }
+}
+
+#[derive(Clone)]
+pub(super) struct Identity(pub(super) native_tls::Identity);
+
+impl Identity {
+    pub(super) fn from_pem(pem: &[u8], key: &[u8]) -> Result<Self, Error> {
+        Ok(Self(
+            native_tls::Identity::from_pkcs8(pem, key).map_err(error::tls)?,
+        ))
+    }
+}
+
+impl Debug for Identity {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        f.debug_struct("Identity").finish_non_exhaustive()
+    }
+}
+
+#[derive(Debug, Copy, Clone, Default)]
+#[non_exhaustive]
+pub(super) enum MinTlsVersion {
+    Tlsv10,
+    Tlsv11,
+    #[default]
+    Tlsv12,
+}

src/transport/smtp/client/tls/rustls.rs

@@ -0,0 +1,329 @@
+use std::{
+    fmt::{self, Debug},
+    sync::Arc,
+};
+
+use rustls::{
+    client::danger::{HandshakeSignatureValid, ServerCertVerified, ServerCertVerifier},
+    crypto::{verify_tls12_signature, verify_tls13_signature, CryptoProvider},
+    pki_types::{self, UnixTime},
+    server::ParsedCertificate,
+    ClientConfig, DigitallySignedStruct, RootCertStore, SignatureScheme,
+};
+
+use crate::transport::smtp::error::{self, Error};
+
+pub(super) fn build_connector(
+    builder: super::TlsParametersBuilder<super::Rustls>,
+) -> Result<(ServerName, Arc<ClientConfig>), Error> {
+    let just_version3 = &[&rustls::version::TLS13];
+    let supported_versions = match builder.min_tls_version {
+        MinTlsVersion::Tlsv12 => rustls::ALL_VERSIONS,
+        MinTlsVersion::Tlsv13 => just_version3,
+    };
+
+    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-platform-verifier")]
+    let mut extra_roots = Vec::new();
+
+    match builder.cert_store {
+        #[cfg(feature = "rustls-platform-verifier")]
+        CertificateStore::PlatformVerifier => {
+            extra_roots = builder
+                .root_certs
+                .iter()
+                .map(|cert| cert.0.clone())
+                .collect();
+        }
+        #[cfg(feature = "rustls-native-certs")]
+        CertificateStore::NativeCerts => {
+            let rustls_native_certs::CertificateResult { certs, errors, .. } =
+                rustls_native_certs::load_native_certs();
+            let errors_len = errors.len();
+
+            let (added, ignored) = root_cert_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(feature = "webpki-roots")]
+        CertificateStore::WebpkiRoots => {
+            root_cert_store.extend(webpki_roots::TLS_SERVER_ROOTS.iter().cloned());
+        }
+        CertificateStore::None => {}
+    }
+    for cert in builder.root_certs {
+        root_cert_store.add(cert.0).map_err(error::tls)?;
+    }
+
+    let tls = match (
+        builder.cert_store,
+        builder.accept_invalid_certs,
+        builder.accept_invalid_hostnames,
+    ) {
+        #[cfg(feature = "rustls-platform-verifier")]
+        (CertificateStore::PlatformVerifier, false, _) => {
+            tls.dangerous().with_custom_certificate_verifier(Arc::new(
+                rustls_platform_verifier::Verifier::new_with_extra_roots(
+                    extra_roots,
+                    crypto_provider,
+                )
+                .map_err(error::tls)?,
+            ))
+        }
+        (_, true, _) | (_, _, true) => {
+            let verifier = InvalidCertsVerifier {
+                ignore_invalid_hostnames: builder.accept_invalid_hostnames,
+                ignore_invalid_certs: builder.accept_invalid_certs,
+                roots: root_cert_store,
+                crypto_provider,
+            };
+            tls.dangerous()
+                .with_custom_certificate_verifier(Arc::new(verifier))
+        }
+        _ => tls.with_root_certificates(root_cert_store),
+    };
+
+    let tls = if let Some(identity) = builder.identity {
+        tls.with_client_auth_cert(identity.chain, identity.key)
+            .map_err(error::tls)?
+    } else {
+        tls.with_no_client_auth()
+    };
+    let server_name = ServerName::try_from(builder.server_name)?;
+    Ok((server_name, Arc::new(tls)))
+}
+
+#[derive(Clone)]
+pub(in crate::transport::smtp) struct ServerName {
+    val: pki_types::ServerName<'static>,
+    str_val: Box<str>,
+}
+
+impl ServerName {
+    #[allow(dead_code)]
+    pub(in crate::transport::smtp) fn inner(self) -> pki_types::ServerName<'static> {
+        self.val
+    }
+
+    pub(in crate::transport::smtp) fn inner_ref(&self) -> &pki_types::ServerName<'static> {
+        &self.val
+    }
+
+    fn try_from(value: String) -> Result<Self, crate::transport::smtp::Error> {
+        let val: pki_types::ServerName<'_> = value
+            .as_str()
+            .try_into()
+            .map_err(crate::transport::smtp::error::tls)?;
+        Ok(Self {
+            val: val.to_owned(),
+            str_val: value.into_boxed_str(),
+        })
+    }
+}
+
+impl AsRef<str> for ServerName {
+    fn as_ref(&self) -> &str {
+        &self.str_val
+    }
+}
+
+#[derive(Debug, Clone, Default)]
+#[allow(dead_code, missing_copy_implementations)]
+#[non_exhaustive]
+pub(super) enum CertificateStore {
+    #[cfg(feature = "rustls-platform-verifier")]
+    #[cfg_attr(docsrs, doc(cfg(feature = "rustls-platform-verifier")))]
+    #[cfg_attr(feature = "rustls-platform-verifier", default)]
+    PlatformVerifier,
+    #[cfg(feature = "rustls-native-certs")]
+    #[cfg_attr(docsrs, doc(cfg(feature = "rustls-native-certs")))]
+    #[cfg_attr(
+        all(
+            not(feature = "rustls-platform-verifier"),
+            feature = "rustls-native-certs",
+        ),
+        default
+    )]
+    NativeCerts,
+    #[cfg(feature = "webpki-roots")]
+    #[cfg_attr(docsrs, doc(cfg(feature = "webpki-roots")))]
+    #[cfg_attr(
+        all(
+            not(feature = "rustls-platform-verifier"),
+            not(feature = "rustls-native-certs"),
+            feature = "webpki-roots",
+        ),
+        default
+    )]
+    WebpkiRoots,
+    #[cfg_attr(
+        all(
+            not(feature = "webpki-roots"),
+            not(feature = "rustls-platform-verifier"),
+            not(feature = "rustls-native-certs")
+        ),
+        default
+    )]
+    None,
+}
+
+#[derive(Clone)]
+pub(super) struct Certificate(pub(super) pki_types::CertificateDer<'static>);
+
+impl Certificate {
+    #[allow(dead_code)]
+    pub(super) fn from_pem(pem: &[u8]) -> Result<Self, Error> {
+        use rustls::pki_types::pem::PemObject as _;
+
+        Ok(Self(
+            pki_types::CertificateDer::from_pem_slice(pem)
+                .map_err(|_| error::tls("invalid certificate"))?,
+        ))
+    }
+
+    pub(super) fn from_pem_bundle(pem: &[u8]) -> Result<Vec<Self>, Error> {
+        use rustls::pki_types::pem::PemObject as _;
+
+        pki_types::CertificateDer::pem_slice_iter(pem)
+            .map(|cert| Ok(Self(cert?)))
+            .collect::<Result<Vec<_>, pki_types::pem::Error>>()
+            .map_err(|_| error::tls("invalid certificate"))
+    }
+
+    pub(super) fn from_der(der: Vec<u8>) -> Self {
+        Self(der.into())
+    }
+}
+
+impl Debug for Certificate {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        f.debug_struct("Certificate").finish_non_exhaustive()
+    }
+}
+
+pub(super) struct Identity {
+    pub(super) chain: Vec<pki_types::CertificateDer<'static>>,
+    pub(super) key: pki_types::PrivateKeyDer<'static>,
+}
+
+impl Identity {
+    pub(super) fn from_pem(pem: &[u8], key: &[u8]) -> Result<Self, Error> {
+        use rustls::pki_types::pem::PemObject as _;
+
+        let key = match pki_types::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(Self {
+            chain: vec![pem.to_owned().into()],
+            key,
+        })
+    }
+}
+
+impl Clone for Identity {
+    fn clone(&self) -> Self {
+        Self {
+            chain: self.chain.clone(),
+            key: self.key.clone_key(),
+        }
+    }
+}
+
+impl Debug for Identity {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        f.debug_struct("Identity").finish_non_exhaustive()
+    }
+}
+
+#[derive(Debug, Copy, Clone, Default)]
+#[non_exhaustive]
+pub(super) enum MinTlsVersion {
+    #[default]
+    Tlsv12,
+    Tlsv13,
+}
+
+#[derive(Debug)]
+struct InvalidCertsVerifier {
+    ignore_invalid_hostnames: bool,
+    ignore_invalid_certs: bool,
+    roots: RootCertStore,
+    crypto_provider: Arc<CryptoProvider>,
+}
+
+impl ServerCertVerifier for InvalidCertsVerifier {
+    fn verify_server_cert(
+        &self,
+        end_entity: &pki_types::CertificateDer<'_>,
+        intermediates: &[pki_types::CertificateDer<'_>],
+        server_name: &pki_types::ServerName<'_>,
+        _ocsp_response: &[u8],
+        now: UnixTime,
+    ) -> Result<ServerCertVerified, rustls::Error> {
+        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: &pki_types::CertificateDer<'_>,
+        dss: &DigitallySignedStruct,
+    ) -> Result<HandshakeSignatureValid, rustls::Error> {
+        verify_tls12_signature(
+            message,
+            cert,
+            dss,
+            &self.crypto_provider.signature_verification_algorithms,
+        )
+    }
+
+    fn verify_tls13_signature(
+        &self,
+        message: &[u8],
+        cert: &pki_types::CertificateDer<'_>,
+        dss: &DigitallySignedStruct,
+    ) -> Result<HandshakeSignatureValid, rustls::Error> {
+        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

@@ -1,5 +1,7 @@
 //! SMTP commands
 
+use std::fmt::{self, Display, Formatter};
+
 use crate::{
     address::Address,
     transport::smtp::{
@@ -9,10 +11,9 @@ use crate::{
         response::Response,
     },
 };
-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>,
@@ -58,7 +59,7 @@ impl Display for Mail {
             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())?;
@@ -270,7 +271,7 @@ impl Auth {
         #[cfg(feature = "tracing")]
         tracing::debug!("auth encoded challenge: {}", encoded_challenge);
 
-        let decoded_base64 = base64::decode(&encoded_challenge).map_err(error::response)?;
+        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);
@@ -288,21 +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(),
+            keyword: "TEST".to_owned(),
-            value: Some("value".to_string()),
+            value: Some("value".to_owned()),
         };
         let rcpt_parameter = RcptParameter::Other {
-            keyword: "TEST".to_string(),
+            keyword: "TEST".to_owned(),
-            value: Some("value".to_string()),
+            value: Some("value".to_owned()),
         };
         assert_eq!(format!("{}", Ehlo::new(id)), "EHLO localhost\r\n");
         assert_eq!(
@@ -339,24 +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!("{Quit}"), "QUIT\r\n");
-        assert_eq!(format!("{}", Data), "DATA\r\n");
+        assert_eq!(format!("{Data}"), "DATA\r\n");
-        assert_eq!(format!("{}", Noop), "NOOP\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!(
+        assert_eq!(format!("{}", Vrfy::new("test".to_owned())), "VRFY test\r\n");
-            format!("{}", Vrfy::new("test".to_string())),
+        assert_eq!(format!("{}", Expn::new("test".to_owned())), "EXPN test\r\n");
-            "VRFY test\r\n"
+        assert_eq!(format!("{Rset}"), "RSET\r\n");
-        );
+        let credentials = Credentials::new("user".to_owned(), "password".to_owned());
-        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!(
                 "{}",

src/transport/smtp/connection_url.rs

@@ -0,0 +1,134 @@
+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;
+    #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+    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)
+    }
+
+    #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+    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)
+    }
+
+    #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+    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

@@ -1,10 +1,11 @@
 //! Error and result type for SMTP clients
 
+use std::{error::Error as StdError, fmt};
+
 use crate::{
     transport::smtp::response::{Code, Severity},
     BoxError,
 };
-use std::{error::Error as StdError, fmt};
 
 // Inspired by https://github.com/seanmonstar/reqwest/blob/a8566383168c0ef06c21f38cbc9213af6ff6db31/src/error.rs
 
@@ -67,12 +68,20 @@ impl Error {
     }
 
     /// Returns true if the error is from TLS
-    #[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-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 {
@@ -101,9 +110,14 @@ pub(crate) enum Kind {
     /// Underlying network i/o error
     Network,
     /// TLS error
-    #[cfg_attr(docsrs, doc(cfg(any(feature = "native-tls", feature = "rustls-tls"))))]
+    #[cfg_attr(
-    #[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
+        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 {
@@ -112,7 +126,7 @@ impl fmt::Debug for Error {
 
         builder.field("kind", &self.inner.kind);
 
-        if let Some(ref source) = self.inner.source {
+        if let Some(source) = &self.inner.source {
             builder.field("source", source);
         }
 
@@ -122,23 +136,24 @@ impl fmt::Debug for Error {
 
 impl fmt::Display for Error {
     fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
-        match self.inner.kind {
+        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-tls"))]
+            #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
             Kind::Tls => f.write_str("tls error")?,
-            Kind::Transient(ref code) => {
+            Kind::TransportShutdown => f.write_str("transport has been shut down")?,
-                write!(f, "transient error ({})", code)?;
+            Kind::Transient(code) => {
+                write!(f, "transient error ({code})")?;
+            }
+            Kind::Permanent(code) => {
+                write!(f, "permanent error ({code})")?;
             }
-            Kind::Permanent(ref code) => {
-                write!(f, "permanent error ({})", code)?;
         }
-        };
 
-        if let Some(ref e) = self.inner.source {
+        if let Some(e) = &self.inner.source {
-            write!(f, ": {}", e)?;
+            write!(f, ": {e}")?;
         }
 
         Ok(())
@@ -154,10 +169,10 @@ impl StdError for Error {
     }
 }
 
-pub(crate) fn code(c: Code) -> Error {
+pub(crate) fn code(c: Code, s: Option<String>) -> Error {
     match c.severity {
-        Severity::TransientNegativeCompletion => Error::new::<Error>(Kind::Transient(c), None),
+        Severity::TransientNegativeCompletion => Error::new(Kind::Transient(c), s),
-        Severity::PermanentNegativeCompletion => Error::new::<Error>(Kind::Permanent(c), None),
+        Severity::PermanentNegativeCompletion => Error::new(Kind::Permanent(c), s),
         _ => client("Unknown error code"),
     }
 }
@@ -178,7 +193,11 @@ pub(crate) fn connection<E: Into<BoxError>>(e: E) -> Error {
     Error::new(Kind::Connection, Some(e))
 }
 
-#[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
+#[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

@@ -1,17 +1,17 @@
 //! ESMTP features
 
+use std::{
+    collections::HashSet,
+    fmt::{self, Display, Formatter},
+    net::{Ipv4Addr, Ipv6Addr},
+};
+
 use crate::transport::smtp::{
     authentication::Mechanism,
     error::{self, Error},
     response::Response,
     util::XText,
 };
-use std::{
-    collections::HashSet,
-    fmt::{self, Display, Formatter},
-    net::{Ipv4Addr, Ipv6Addr},
-    result::Result,
-};
 
 /// Client identifier, the parameter to `EHLO`
 #[derive(PartialEq, Eq, Clone, Debug)]
@@ -52,10 +52,10 @@ impl Default for ClientId {
 
 impl Display for ClientId {
     fn fmt(&self, f: &mut Formatter<'_>) -> fmt::Result {
-        match *self {
+        match self {
-            Self::Domain(ref value) => f.write_str(value),
+            Self::Domain(value) => f.write_str(value),
-            Self::Ipv4(ref value) => write!(f, "[{}]", value),
+            Self::Ipv4(value) => write!(f, "[{value}]"),
-            Self::Ipv6(ref value) => write!(f, "[IPv6:{}]", value),
+            Self::Ipv6(value) => write!(f, "[IPv6:{value}]"),
         }
     }
 }
@@ -92,11 +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}"),
         }
     }
 }
@@ -118,7 +118,7 @@ pub struct ServerInfo {
 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)
         };
@@ -129,9 +129,8 @@ 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() {
+        let Some(name) = response.first_word() else {
-            Some(name) => name,
+            return Err(error::response("Could not read server name"));
-            None => return Err(error::response("Could not read server name")),
         };
 
         let mut features: HashSet<Extension> = HashSet::new();
@@ -169,11 +168,11 @@ impl ServerInfo {
                     }
                 }
                 _ => (),
-            };
+            }
         }
 
         Ok(ServerInfo {
-            name: name.to_string(),
+            name: name.to_owned(),
             features,
         })
     }
@@ -189,7 +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) {
@@ -226,16 +225,16 @@ pub enum MailParameter {
 
 impl Display for MailParameter {
     fn fmt(&self, f: &mut Formatter<'_>) -> fmt::Result {
-        match *self {
+        match self {
-            MailParameter::Body(ref value) => write!(f, "BODY={}", value),
+            MailParameter::Body(value) => write!(f, "BODY={value}"),
-            MailParameter::Size(size) => write!(f, "SIZE={}", size),
+            MailParameter::Size(size) => write!(f, "SIZE={size}"),
             MailParameter::SmtpUtfEight => f.write_str("SMTPUTF8"),
             MailParameter::Other {
-                ref keyword,
+                keyword,
-                value: Some(ref value),
+                value: Some(value),
             } => write!(f, "{}={}", keyword, XText(value)),
             MailParameter::Other {
-                ref keyword,
+                keyword,
                 value: None,
             } => f.write_str(keyword),
         }
@@ -276,13 +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,
+                keyword,
-                value: Some(ref value),
+                value: Some(value),
-            } => write!(f, "{}={}", keyword, XText(value)),
+            } => write!(f, "{keyword}={}", XText(value)),
             RcptParameter::Other {
-                ref keyword,
+                keyword,
                 value: None,
             } => f.write_str(keyword),
         }
@@ -291,32 +290,27 @@ impl Display for RcptParameter {
 
 #[cfg(test)]
 mod test {
-
     use super::*;
-    use crate::transport::smtp::{
+    use crate::transport::smtp::response::{Category, Code, Detail, Severity};
-        authentication::Mechanism,
-        response::{Category, Code, Detail, Response, Severity},
-    };
-    use std::collections::HashSet;
 
     #[test]
     fn test_clientid_fmt() {
         assert_eq!(
-            format!("{}", ClientId::Domain("test".to_string())),
+            format!("{}", ClientId::Domain("test".to_owned())),
-            "test".to_string()
+            "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()
         );
     }
 
@@ -329,11 +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();
@@ -342,11 +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();
@@ -356,11 +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()
         );
     }
 
@@ -372,18 +366,14 @@ mod test {
                 Category::Unspecified4,
                 Detail::One,
             ),
-            vec![
+            vec!["me".to_owned(), "8BITMIME".to_owned(), "SIZE 42".to_owned()],
-                "me".to_string(),
-                "8BITMIME".to_string(),
-                "SIZE 42".to_string(),
-            ],
         );
 
         let mut features = HashSet::new();
         assert!(features.insert(Extension::EightBitMime));
 
         let server_info = ServerInfo {
-            name: "me".to_string(),
+            name: "me".to_owned(),
             features,
         };
 
@@ -399,10 +389,10 @@ mod test {
                 Detail::One,
             ),
             vec![
-                "me".to_string(),
+                "me".to_owned(),
-                "AUTH PLAIN CRAM-MD5 XOAUTH2 OTHER".to_string(),
+                "AUTH PLAIN CRAM-MD5 XOAUTH2 OTHER".to_owned(),
-                "8BITMIME".to_string(),
+                "8BITMIME".to_owned(),
-                "SIZE 42".to_string(),
+                "SIZE 42".to_owned(),
             ],
         );
 
@@ -412,7 +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

@@ -26,95 +26,170 @@
 //!
 //! 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
+//! // Create the SMTPS transport
 //! let sender = SmtpTransport::relay("smtp.example.com")?
-//!     .build();
-//! // Send the email via remote relay
-//! let result = sender.send(&email);
-//! assert!(result.is_ok());
-//! # Ok(())
-//! # }
-//! ```
-//!
-//! #### Authentication
-//!
-//! Example with authentication and connection pool:
-//!
-//! ```rust,no_run
-//! # #[cfg(all(feature = "builder", any(feature = "native-tls", feature = "rustls-tls")))]
-//! # fn test() -> Result<(), Box<dyn std::error::Error>> {
-//! use lettre::{Message, Transport, SmtpTransport, transport::smtp::{PoolConfig, authentication::{Credentials, Mechanism}}};
-//!
-//! 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!"))?;
-//!
-//! // Create TLS transport on port 587 with STARTTLS
-//! let sender = SmtpTransport::starttls_relay("smtp.example.com")?
 //!     // Add credentials for authentication
-//!     .credentials(Credentials::new("username".to_string(), "password".to_string()))
+//!     .credentials(Credentials::new(
-//!     // Configure expected authentication mechanism
+//!         "username".to_owned(),
+//!         "password".to_owned(),
+//!     ))
+//!     // Optionally configure expected authentication mechanism
 //!     .authentication(vec![Mechanism::Plain])
-//!     // Connection pool settings
-//!     .pool_config( PoolConfig::new().max_size(20))
 //!     .build();
 //!
 //! // Send the email via remote relay
-//! let result = sender.send(&email);
+//! sender.send(&email)?;
-//! assert!(result.is_ok());
 //! # Ok(())
 //! # }
 //! ```
 //!
-//! You can specify custom TLS settings:
+//! #### Shortening configuration
+//!
+//! 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.
+//!
+//! For more information take a look at [`SmtpTransport::from_url`] or [`AsyncSmtpTransport::from_url`].
 //!
 //! ```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, transport::smtp::client::{TlsParameters, Tls}};
+//! 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!"))?;
 //!
-//! // Custom TLS configuration
+//! // Create the SMTPS transport
-//! let tls = TlsParameters::builder("smtp.example.com".to_string())
+//! let sender = SmtpTransport::from_url("smtps://username:password@smtp.example.com")?.build();
-//!           .dangerous_accept_invalid_certs(true).build()?;
-//!
-//! // Create TLS transport on port 465
-//! let sender = SmtpTransport::relay("smtp.example.com")?
-//!     // Custom TLS configuration
-//!     .tls(Tls::Required(tls))
-//!     .build();
 //!
 //! // Send the email via remote relay
-//! let result = sender.send(&email);
+//! sender.send(&email)?;
-//! assert!(result.is_ok());
 //! # 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())
+//! }
+//! # }
+//! ```
+
+use std::time::Duration;
+
+use client::Tls;
 
 #[cfg(any(feature = "tokio1", feature = "async-std1"))]
 pub use self::async_transport::{AsyncSmtpTransport, AsyncSmtpTransportBuilder};
@@ -124,7 +199,7 @@ 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},
@@ -132,14 +207,13 @@ use crate::transport::smtp::{
     extension::ClientId,
     response::Response,
 };
-use client::Tls;
-use std::time::Duration;
 
 #[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 = "pool")]
@@ -186,7 +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/async_impl.rs

@@ -1,26 +1,30 @@
-use std::fmt::{self, Debug};
+use std::{
-use std::mem;
+    fmt::{self, Debug},
-use std::ops::{Deref, DerefMut};
+    ops::{Deref, DerefMut},
-use std::sync::Arc;
+    sync::{Arc, OnceLock},
-use std::time::{Duration, Instant};
+    time::{Duration, Instant},
+};
 
-use futures_util::lock::Mutex;
+use futures_util::{
-use futures_util::stream::{self, StreamExt};
+    lock::Mutex,
-use once_cell::sync::OnceCell;
+    stream::{self, StreamExt},
+};
 
-use crate::executor::SpawnHandle;
+use super::{
-use crate::transport::smtp::async_transport::AsyncSmtpClient;
+    super::{client::AsyncSmtpConnection, Error},
-use crate::Executor;
+    PoolConfig,
+};
+use crate::{
+    executor::SpawnHandle,
+    transport::smtp::{async_transport::AsyncSmtpClient, error},
+    Executor,
+};
 
-use super::super::client::AsyncSmtpConnection;
+pub(crate) struct Pool<E: Executor> {
-use super::super::Error;
-use super::PoolConfig;
-
-pub struct Pool<E: Executor> {
     config: PoolConfig,
-    connections: Mutex<Vec<ParkedConnection>>,
+    connections: Mutex<Option<Vec<ParkedConnection>>>,
     client: AsyncSmtpClient<E>,
-    handle: OnceCell<E::Handle>,
+    handle: OnceLock<E::Handle>,
 }
 
 struct ParkedConnection {
@@ -28,18 +32,18 @@ struct ParkedConnection {
     since: Instant,
 }
 
-pub struct PooledConnection<E: Executor> {
+pub(crate) struct PooledConnection<E: Executor> {
     conn: Option<AsyncSmtpConnection>,
     pool: Arc<Pool<E>>,
 }
 
 impl<E: Executor> Pool<E> {
-    pub fn new(config: PoolConfig, client: AsyncSmtpClient<E>) -> Arc<Self> {
+    pub(crate) fn new(config: PoolConfig, client: AsyncSmtpClient<E>) -> Arc<Self> {
         let pool = Arc::new(Self {
             config,
-            connections: Mutex::new(Vec::new()),
+            connections: Mutex::new(Some(Vec::new())),
             client,
-            handle: OnceCell::new(),
+            handle: OnceLock::new(),
         });
 
         {
@@ -59,6 +63,10 @@ impl<E: Executor> Pool<E> {
                             #[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()
@@ -77,7 +85,7 @@ impl<E: Executor> Pool<E> {
 
                             #[cfg(feature = "tracing")]
                             let mut created = 0;
-                            for _ in count..=(min_idle as usize) {
+                            for _ in count..(min_idle as usize) {
                                 let conn = match pool.client.connection().await {
                                     Ok(conn) => conn,
                                     Err(err) => {
@@ -91,6 +99,11 @@ impl<E: Executor> Pool<E> {
                                 };
 
                                 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")]
@@ -108,7 +121,7 @@ impl<E: Executor> Pool<E> {
                                 #[cfg(feature = "tracing")]
                                 tracing::debug!("dropped {} idle connections", dropped.len());
 
-                                abort_concurrent(dropped.into_iter().map(|conn| conn.unpark()))
+                                abort_concurrent(dropped.into_iter().map(ParkedConnection::unpark))
                                     .await;
                             }
                         }
@@ -133,10 +146,25 @@ impl<E: Executor> Pool<E> {
         pool
     }
 
-    pub async fn connection(self: &Arc<Self>) -> Result<PooledConnection<E>, Error> {
+    pub(crate) async fn shutdown(&self) {
+        let connections = { self.connections.lock().await.take() };
+        if let Some(connections) = connections {
+            abort_concurrent(connections.into_iter().map(ParkedConnection::unpark)).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()
             };
 
@@ -156,14 +184,14 @@ impl<E: Executor> Pool<E> {
                     #[cfg(feature = "tracing")]
                     tracing::debug!("reusing a pooled connection");
 
-                    return Ok(PooledConnection::wrap(conn, self.clone()));
+                    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, self.clone()));
+                    return Ok(PooledConnection::wrap(conn, Arc::clone(self)));
                 }
             }
         }
@@ -180,14 +208,21 @@ impl<E: Executor> Pool<E> {
             #[cfg(feature = "tracing")]
             tracing::debug!("recycling connection");
 
-            let mut connections = self.connections.lock().await;
+            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);
+                    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;
+            }
         }
     }
 }
@@ -199,9 +234,15 @@ impl<E: Executor> Debug for Pool<E> {
             .field(
                 "connections",
                 &match self.connections.try_lock() {
-                    Some(connections) => format!("{} connections", connections.len()),
+                    Some(connections) => {
+                        if let Some(connections) = connections.as_ref() {
+                            format!("{} connections", connections.len())
+                        } else {
+                            "SHUT DOWN".to_owned()
+                        }
+                    }
 
-                    None => "LOCKED".to_string(),
+                    None => "LOCKED".to_owned(),
                 },
             )
             .field("client", &self.client)
@@ -221,14 +262,16 @@ impl<E: Executor> Drop for Pool<E> {
         #[cfg(feature = "tracing")]
         tracing::debug!("dropping Pool");
 
-        let connections = mem::take(self.connections.get_mut());
+        let connections = self.connections.get_mut().take();
         let handle = self.handle.take();
         E::spawn(async move {
             if let Some(handle) = handle {
                 handle.shutdown().await;
             }
 
-            abort_concurrent(connections.into_iter().map(|conn| conn.unpark())).await;
+            if let Some(connections) = connections {
+                abort_concurrent(connections.into_iter().map(ParkedConnection::unpark)).await;
+            }
         });
     }
 }

src/transport/smtp/pool/mod.rs

@@ -1,8 +1,8 @@
 use std::time::Duration;
 
 #[cfg(any(feature = "tokio1", feature = "async-std1"))]
-pub mod async_impl;
+pub(super) mod async_impl;
-pub mod sync_impl;
+pub(super) mod sync_impl;
 
 /// Configuration for a connection pool
 #[derive(Debug, Clone)]

src/transport/smtp/pool/sync_impl.rs

@@ -1,18 +1,21 @@
-use std::fmt::{self, Debug};
+use std::{
-use std::ops::{Deref, DerefMut};
+    fmt::{self, Debug},
-use std::sync::{Arc, Mutex, TryLockError};
+    ops::{Deref, DerefMut},
-use std::time::{Duration, Instant};
+    sync::{mpsc, Arc, Mutex, TryLockError},
-use std::{mem, thread};
+    thread,
+    time::{Duration, Instant},
+};
 
-use crate::transport::smtp::transport::SmtpClient;
+use super::{
+    super::{client::SmtpConnection, Error},
+    PoolConfig,
+};
+use crate::transport::smtp::{error, transport::SmtpClient};
 
-use super::super::client::SmtpConnection;
+pub(crate) struct Pool {
-use super::super::Error;
-use super::PoolConfig;
-
-pub struct Pool {
     config: PoolConfig,
-    connections: Mutex<Vec<ParkedConnection>>,
+    connections: Mutex<Option<Vec<ParkedConnection>>>,
+    thread_terminator: mpsc::SyncSender<()>,
     client: SmtpClient,
 }
 
@@ -21,16 +24,19 @@ struct ParkedConnection {
     since: Instant,
 }
 
-pub struct PooledConnection {
+pub(crate) struct PooledConnection {
     conn: Option<SmtpConnection>,
     pool: Arc<Pool>,
 }
 
 impl Pool {
-    pub fn new(config: PoolConfig, client: SmtpClient) -> Arc<Self> {
+    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(Vec::new()),
+            connections: Mutex::new(Some(Vec::new())),
+            thread_terminator: thread_tx,
             client,
         });
 
@@ -51,6 +57,10 @@ impl Pool {
                         #[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()
@@ -69,7 +79,7 @@ impl Pool {
 
                         #[cfg(feature = "tracing")]
                         let mut created = 0;
-                        for _ in count..=(min_idle as usize) {
+                        for _ in count..(min_idle as usize) {
                             let conn = match pool.client.connection() {
                                 Ok(conn) => conn,
                                 Err(err) => {
@@ -83,6 +93,11 @@ impl Pool {
                             };
 
                             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")]
@@ -106,7 +121,15 @@ impl Pool {
                             }
                         }
 
-                        thread::sleep(idle_timeout);
+                        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");
@@ -115,10 +138,25 @@ impl Pool {
         pool
     }
 
-    pub fn connection(self: &Arc<Self>) -> Result<PooledConnection, Error> {
+    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()
             };
 
@@ -138,14 +176,14 @@ impl Pool {
                     #[cfg(feature = "tracing")]
                     tracing::debug!("reusing a pooled connection");
 
-                    return Ok(PooledConnection::wrap(conn, self.clone()));
+                    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, self.clone()));
+                    return Ok(PooledConnection::wrap(conn, Arc::clone(self)));
                 }
             }
         }
@@ -162,14 +200,21 @@ impl Pool {
             #[cfg(feature = "tracing")]
             tracing::debug!("recycling connection");
 
-            let mut connections = self.connections.lock().unwrap();
+            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);
+                    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();
+            }
         }
     }
 }
@@ -181,10 +226,16 @@ impl Debug for Pool {
             .field(
                 "connections",
                 &match self.connections.try_lock() {
-                    Ok(connections) => format!("{} connections", connections.len()),
+                    Ok(connections) => {
+                        if let Some(connections) = connections.as_ref() {
+                            format!("{} connections", connections.len())
+                        } else {
+                            "SHUT DOWN".to_owned()
+                        }
+                    }
 
-                    Err(TryLockError::WouldBlock) => "LOCKED".to_string(),
+                    Err(TryLockError::WouldBlock) => "LOCKED".to_owned(),
-                    Err(TryLockError::Poisoned(_)) => "POISONED".to_string(),
+                    Err(TryLockError::Poisoned(_)) => "POISONED".to_owned(),
                 },
             )
             .field("client", &self.client)
@@ -197,12 +248,13 @@ impl Drop for Pool {
         #[cfg(feature = "tracing")]
         tracing::debug!("dropping Pool");
 
-        let connections = mem::take(&mut *self.connections.get_mut().unwrap());
+        if let Some(connections) = self.connections.get_mut().unwrap().take() {
             for conn in connections {
                 let mut conn = conn.unpark();
                 conn.abort();
             }
         }
+    }
 }
 
 impl ParkedConnection {

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, 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},
+    sequence::preceded,
-    IResult,
+    IResult, Parser,
-};
-use std::{
-    fmt::{Display, Formatter, Result},
-    result,
-    str::FromStr,
-    string::ToString,
 };
 
-/// 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 {
@@ -130,6 +131,12 @@ impl Code {
     }
 }
 
+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
 ///
 /// The text message is optional, only the code is mandatory
@@ -149,7 +156,7 @@ impl FromStr for Response {
     fn from_str(s: &str) -> result::Result<Response, Error> {
         parse_response(s)
             .map(|(_, r)| r)
-            .map_err(|e| error::response(e.to_string()))
+            .map_err(|e| error::response(e.to_owned()))
     }
 }
 
@@ -214,7 +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> {
@@ -225,7 +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> {
@@ -240,18 +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)?;
+        (parse_code, preceded(tag(" "), take_until("\r\n"))).parse(i)?;
-    let (i, _) = complete(tag("\r\n"))(i)?;
+    let (i, _) = complete(tag("\r\n")).parse(i)?;
 
     // Check that all codes are equal.
     if !lines.iter().all(|&(code, _, _)| code == last_code) {
@@ -315,6 +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";
@@ -327,10 +349,10 @@ mod test {
                     detail: Detail::Zero,
                 },
                 message: vec![
-                    "me".to_string(),
+                    "me".to_owned(),
-                    "8BITMIME".to_string(),
+                    "8BITMIME".to_owned(),
-                    "SIZE 42".to_string(),
+                    "SIZE 42".to_owned(),
-                    "AUTH PLAIN CRAM-MD5".to_string(),
+                    "AUTH PLAIN CRAM-MD5".to_owned(),
                 ],
             }
         );
@@ -350,11 +372,7 @@ mod test {
                 category: Category::MailSystem,
                 detail: Detail::Zero,
             },
-            vec![
+            vec!["me".to_owned(), "8BITMIME".to_owned(), "SIZE 42".to_owned(),],
-                "me".to_string(),
-                "8BITMIME".to_string(),
-                "SIZE 42".to_string(),
-            ],
         )
         .is_positive());
         assert!(!Response::new(
@@ -363,11 +381,7 @@ mod test {
                 category: Category::MailSystem,
                 detail: Detail::Zero,
             },
-            vec![
+            vec!["me".to_owned(), "8BITMIME".to_owned(), "SIZE 42".to_owned(),],
-                "me".to_string(),
-                "8BITMIME".to_string(),
-                "SIZE 42".to_string(),
-            ],
         )
         .is_positive());
     }
@@ -380,11 +394,7 @@ mod test {
                 category: Category::MailSystem,
                 detail: Detail::One,
             },
-            vec![
+            vec!["me".to_owned(), "8BITMIME".to_owned(), "SIZE 42".to_owned(),],
-                "me".to_string(),
-                "8BITMIME".to_string(),
-                "SIZE 42".to_string(),
-            ],
         )
         .has_code(451));
         assert!(!Response::new(
@@ -393,11 +403,7 @@ mod test {
                 category: Category::MailSystem,
                 detail: Detail::One,
             },
-            vec![
+            vec!["me".to_owned(), "8BITMIME".to_owned(), "SIZE 42".to_owned(),],
-                "me".to_string(),
-                "8BITMIME".to_string(),
-                "SIZE 42".to_string(),
-            ],
         )
         .has_code(251));
     }
@@ -411,11 +417,7 @@ mod test {
                     category: Category::MailSystem,
                     detail: Detail::One,
                 },
-                vec![
+                vec!["me".to_owned(), "8BITMIME".to_owned(), "SIZE 42".to_owned(),],
-                    "me".to_string(),
-                    "8BITMIME".to_string(),
-                    "SIZE 42".to_string(),
-                ],
             )
             .first_word(),
             Some("me")
@@ -428,9 +430,9 @@ mod test {
                     detail: Detail::One,
                 },
                 vec![
-                    "me mo".to_string(),
+                    "me mo".to_owned(),
-                    "8BITMIME".to_string(),
+                    "8BITMIME".to_owned(),
-                    "SIZE 42".to_string(),
+                    "SIZE 42".to_owned(),
                 ],
             )
             .first_word(),
@@ -455,7 +457,7 @@ mod test {
                     category: Category::MailSystem,
                     detail: Detail::One,
                 },
-                vec![" ".to_string()],
+                vec![" ".to_owned()],
             )
             .first_word(),
             None
@@ -467,7 +469,7 @@ mod test {
                     category: Category::MailSystem,
                     detail: Detail::One,
                 },
-                vec!["  ".to_string()],
+                vec!["  ".to_owned()],
             )
             .first_word(),
             None
@@ -479,7 +481,7 @@ mod test {
                     category: Category::MailSystem,
                     detail: Detail::One,
                 },
-                vec!["".to_string()],
+                vec!["".to_owned()],
             )
             .first_word(),
             None
@@ -492,7 +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:?}"),
         }
     }
 
@@ -505,11 +507,7 @@ mod test {
                     category: Category::MailSystem,
                     detail: Detail::One,
                 },
-                vec![
+                vec!["me".to_owned(), "8BITMIME".to_owned(), "SIZE 42".to_owned(),],
-                    "me".to_string(),
-                    "8BITMIME".to_string(),
-                    "SIZE 42".to_string(),
-                ],
             )
             .first_line(),
             Some("me")
@@ -522,9 +520,9 @@ mod test {
                     detail: Detail::One,
                 },
                 vec![
-                    "me mo".to_string(),
+                    "me mo".to_owned(),
-                    "8BITMIME".to_string(),
+                    "8BITMIME".to_owned(),
-                    "SIZE 42".to_string(),
+                    "SIZE 42".to_owned(),
                 ],
             )
             .first_line(),
@@ -549,7 +547,7 @@ mod test {
                     category: Category::MailSystem,
                     detail: Detail::One,
                 },
-                vec![" ".to_string()],
+                vec![" ".to_owned()],
             )
             .first_line(),
             Some(" ")
@@ -561,7 +559,7 @@ mod test {
                     category: Category::MailSystem,
                     detail: Detail::One,
                 },
-                vec!["  ".to_string()],
+                vec!["  ".to_owned()],
             )
             .first_line(),
             Some("  ")
@@ -573,7 +571,7 @@ mod test {
                     category: Category::MailSystem,
                     detail: Detail::One,
                 },
-                vec!["".to_string()],
+                vec!["".to_owned()],
             )
             .first_line(),
             Some("")

src/transport/smtp/transport.rs

@@ -1,17 +1,41 @@
 #[cfg(feature = "pool")]
 use std::sync::Arc;
-use std::time::Duration;
+use std::{fmt::Debug, time::Duration};
 
 #[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, Transport};
 
-/// Sends emails using the SMTP protocol
+/// 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 {
@@ -32,10 +56,23 @@ impl Transport for SmtpTransport {
         let result = conn.send(envelope, email)?;
 
         #[cfg(not(feature = "pool"))]
-        conn.quit()?;
+        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 {
@@ -45,8 +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-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())?;
 
@@ -55,7 +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.
@@ -66,8 +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-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())?;
 
@@ -89,29 +132,122 @@ 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 {
+        SmtpTransportBuilder::new(server)
-            server: server.into(),
-            ..Default::default()
-        };
-
-        SmtpTransportBuilder {
-            info: new,
-            #[cfg(feature = "pool")]
-            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
+    /// # const TOML: &str = 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 afterwards if a connection pool is not used.
+    /// 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()?;
 
@@ -135,13 +271,27 @@ pub struct SmtpTransportBuilder {
 
 /// 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
@@ -160,14 +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"))]
+    ///
-    #[cfg_attr(docsrs, doc(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
@@ -185,7 +360,7 @@ impl SmtpTransportBuilder {
 
     /// Build the transport
     ///
-    /// If the `pool` 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 };
@@ -199,7 +374,7 @@ impl SmtpTransportBuilder {
 
 /// Build client
 #[derive(Debug, Clone)]
-pub struct SmtpClient {
+pub(super) struct SmtpClient {
     info: SmtpInfo,
 }
 
@@ -207,11 +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 {
+        let tls_parameters = match &self.info.tls {
-            #[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
+            #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
-            Tls::Wrapper(ref tls_parameters) => Some(tls_parameters),
+            Tls::Wrapper(tls_parameters) => Some(tls_parameters),
             _ => None,
         };
 
@@ -221,16 +396,17 @@ impl SmtpClient {
             self.info.timeout,
             &self.info.hello_name,
             tls_parameters,
+            None,
         )?;
 
-        #[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
+        #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
-        match self.info.tls {
+        match &self.info.tls {
-            Tls::Opportunistic(ref tls_parameters) => {
+            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)?;
             }
             _ => (),
@@ -242,3 +418,78 @@ impl SmtpClient {
         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

@@ -4,9 +4,9 @@ use std::fmt::{Display, Formatter, Result as FmtResult};
 
 /// Encode a string as xtext
 #[derive(Debug)]
-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 == '=') {
@@ -38,10 +38,8 @@ mod tests {
             ("bjørn", "bjørn"),
             ("Ø+= ❤️‰", "Ø+2B+3D+20❤️‰"),
             ("+", "+2B"),
-        ]
+        ] {
-        .iter()
+            assert_eq!(format!("{}", XText(input)), (*expect).to_owned());
-        {
-            assert_eq!(format!("{}", XText(input)), expect.to_string());
         }
     }
 }

src/transport/stub/mod.rs

@@ -1,40 +1,60 @@
-//! The stub transport only logs message envelope and drops the content. It can be useful for
+//! The stub transport logs message envelopes as well as contents. It can be useful for testing
-//! testing purposes.
+//! purposes.
 //!
-//! #### Stub Transport
+//! # Stub Transport
 //!
-//! The stub transport returns provided result and drops the content. It can be useful for
+//! The stub transport logs message envelopes as well as contents. It can be useful for testing
-//! testing purposes.
+//! purposes.
+//!
+//! # Examples
 //!
 //! ```rust
 //! # #[cfg(feature = "builder")]
 //! # {
-//! use lettre::{transport::stub::StubTransport, Message, Transport};
+//! 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);
+//! sender.send(&email)?;
-//! assert!(result.is_ok());
+//! assert_eq!(
+//!     sender.messages(),
+//!     vec![(
+//!         email.envelope().clone(),
+//!         String::from_utf8(email.formatted()).unwrap()
+//!     )],
+//! );
 //! # Ok(())
 //! # }
+//! # try_main().unwrap();
 //! # }
 //! ```
 
+use std::{
+    error::Error as StdError,
+    fmt,
+    sync::{Arc, Mutex},
+};
+
+#[cfg(any(feature = "tokio1", feature = "async-std1"))]
+use async_trait::async_trait;
+
 #[cfg(any(feature = "tokio1", feature = "async-std1"))]
 use crate::AsyncTransport;
 use crate::{address::Envelope, Transport};
-#[cfg(any(feature = "tokio1", feature = "async-std1"))]
-use async_trait::async_trait;
-use std::{error::Error as StdError, fmt};
 
+/// An error returned by the stub transport
+#[non_exhaustive]
 #[derive(Debug, Copy, Clone)]
 pub struct Error;
 
@@ -46,47 +66,113 @@ impl fmt::Display for Error {
 
 impl StdError for Error {}
 
-/// This transport logs the message envelope and returns the given response
+/// This transport logs messages and always returns the given response
-#[derive(Debug, Clone, Copy)]
+#[derive(Debug, Clone)]
 pub struct StubTransport {
     response: Result<(), Error>,
+    message_log: Arc<Mutex<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<Mutex<Vec<(Envelope, String)>>>,
 }
 
 impl StubTransport {
     /// Creates a new transport that always returns the given Result
-    pub fn new(response: Result<(), Error>) -> StubTransport {
+    pub fn new(response: Result<(), Error>) -> Self {
-        StubTransport { response }
+        Self {
+            response,
+            message_log: Arc::new(Mutex::new(vec![])),
+        }
     }
 
     /// Creates a new transport that always returns a success response
-    pub fn new_ok() -> StubTransport {
+    pub fn new_ok() -> Self {
-        StubTransport { response: Ok(()) }
+        Self {
+            response: Ok(()),
+            message_log: Arc::new(Mutex::new(vec![])),
+        }
     }
 
     /// Creates a new transport that always returns an error
-    pub fn new_error() -> StubTransport {
+    pub fn new_error() -> Self {
-        StubTransport {
+        Self {
             response: Err(Error),
+            message_log: Arc::new(Mutex::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(Mutex::new(vec![])),
+        }
+    }
+
+    /// Creates a new transport that always returns a success response
+    pub fn new_ok() -> Self {
+        Self {
+            response: Ok(()),
+            message_log: Arc::new(Mutex::new(vec![])),
+        }
+    }
+
+    /// Creates a new transport that always returns an error
+    pub fn new_error() -> Self {
+        Self {
+            response: Err(Error),
+            message_log: Arc::new(Mutex::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().unwrap().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(any(feature = "tokio1", feature = "async-std1"))]
 #[async_trait]
-impl AsyncTransport 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> {
+    async fn send_raw(&self, envelope: &Envelope, email: &[u8]) -> Result<Self::Ok, Self::Error> {
+        self.message_log
+            .lock()
+            .unwrap()
+            .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

@@ -1,4 +1,4 @@
-Date: Tue, 15 Nov 1994 08:12:31 -0000
+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>

tests/transport_file.rs

@@ -9,13 +9,15 @@ fn default_date() -> std::time::SystemTime {
 #[cfg(test)]
 #[cfg(all(feature = "file-transport", feature = "builder"))]
 mod sync {
-    use crate::default_date;
-    use lettre::{FileTransport, Message, Transport};
     use std::{
         env::temp_dir,
         fs::{read_to_string, remove_file},
     };
 
+    use lettre::{FileTransport, Message, Transport};
+
+    use crate::default_date;
+
     #[test]
     fn file_transport() {
         let sender = FileTransport::new(temp_dir());
@@ -31,7 +33,7 @@ mod sync {
         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!(
@@ -41,7 +43,7 @@ mod sync {
                 "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",
+                "Date: Tue, 15 Nov 1994 08:12:31 +0000\r\n",
                 "Content-Transfer-Encoding: 7bit\r\n",
                 "\r\n",
                 "Be happy!"
@@ -66,10 +68,10 @@ mod sync {
         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!(
@@ -79,7 +81,7 @@ mod sync {
                 "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",
+                "Date: Tue, 15 Nov 1994 08:12:31 +0000\r\n",
                 "Content-Transfer-Encoding: 7bit\r\n",
                 "\r\n",
                 "Be happy!"
@@ -104,15 +106,16 @@ mod sync {
 #[cfg(test)]
 #[cfg(all(feature = "file-transport", feature = "builder", feature = "tokio1"))]
 mod tokio_1 {
-    use crate::default_date;
-    use lettre::{AsyncFileTransport, AsyncTransport, Message, Tokio1Executor};
     use std::{
         env::temp_dir,
         fs::{read_to_string, remove_file},
     };
 
+    use lettre::{AsyncFileTransport, AsyncTransport, Message, Tokio1Executor};
     use tokio1_crate as tokio;
 
+    use crate::default_date;
+
     #[tokio::test]
     async fn file_transport_tokio1() {
         let sender = AsyncFileTransport::<Tokio1Executor>::new(temp_dir());
@@ -128,7 +131,7 @@ mod tokio_1 {
         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!(
@@ -138,7 +141,7 @@ mod tokio_1 {
                 "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",
+                "Date: Tue, 15 Nov 1994 08:12:31 +0000\r\n",
                 "Content-Transfer-Encoding: 7bit\r\n",
                 "\r\n",
                 "Be happy!"
@@ -155,13 +158,15 @@ mod tokio_1 {
     feature = "async-std1"
 ))]
 mod asyncstd_1 {
-    use crate::default_date;
-    use lettre::{AsyncFileTransport, AsyncStd1Executor, AsyncTransport, Message};
     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());
@@ -177,7 +182,7 @@ mod asyncstd_1 {
         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!(
@@ -187,7 +192,7 @@ mod asyncstd_1 {
                 "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",
+                "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

@@ -15,7 +15,7 @@ mod sync {
             .unwrap();
 
         let result = sender.send(&email);
-        println!("{:?}", result);
+        println!("{result:?}");
         assert!(result.is_ok());
     }
 }
@@ -42,7 +42,7 @@ mod tokio_1 {
             .unwrap();
 
         let result = sender.send(email).await;
-        println!("{:?}", result);
+        println!("{result:?}");
         assert!(result.is_ok());
     }
 }
@@ -68,7 +68,7 @@ mod asyncstd_1 {
             .unwrap();
 
         let result = sender.send(email).await;
-        println!("{:?}", result);
+        println!("{result:?}");
         assert!(result.is_ok());
     }
 }

tests/transport_smtp.rs

@@ -24,7 +24,6 @@ mod sync {
 #[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]

tests/transport_smtp_pool.rs

@@ -1,8 +1,9 @@
 #[cfg(all(test, feature = "smtp-transport", feature = "pool"))]
 mod sync {
-    use lettre::{address::Envelope, SmtpTransport, Transport};
     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

@@ -17,20 +17,25 @@ mod sync {
 
         sender_ok.send(&email).unwrap();
         sender_ko.send(&email).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::StubTransport, AsyncTransport, Message};
+    use lettre::{transport::stub::AsyncStubTransport, AsyncTransport, Message};
-
     use tokio1_crate as tokio;
 
     #[tokio::test]
     async fn stub_transport_tokio1() {
-        let sender_ok = StubTransport::new_ok();
+        let sender_ok = AsyncStubTransport::new_ok();
-        let sender_ko = StubTransport::new_error();
+        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())
@@ -40,19 +45,25 @@ mod tokio_1 {
             .unwrap();
 
         sender_ok.send(email.clone()).await.unwrap();
-        sender_ko.send(email).await.unwrap_err();
+        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::StubTransport, AsyncTransport, Message};
+    use lettre::{transport::stub::AsyncStubTransport, AsyncTransport, Message};
 
     #[async_std::test]
     async fn stub_transport_asyncstd1() {
-        let sender_ok = StubTransport::new_ok();
+        let sender_ok = AsyncStubTransport::new_ok();
-        let sender_ko = StubTransport::new_error();
+        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())
@@ -62,6 +73,12 @@ mod asyncstd_1 {
             .unwrap();
 
         sender_ok.send(email.clone()).await.unwrap();
-        sender_ko.send(email).await.unwrap_err();
+        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);
     }
 }