Fix warnings

Bumps [mio](https://github.com/tokio-rs/mio) from 0.8.10 to 0.8.11.
- [Release notes](https://github.com/tokio-rs/mio/releases)
- [Changelog](https://github.com/tokio-rs/mio/blob/master/CHANGELOG.md)
- [Commits](https://github.com/tokio-rs/mio/compare/v0.8.10...v0.8.11)

---
updated-dependencies:
- dependency-name: mio
  dependency-type: indirect
...

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

.github/workflows/test.yml

@@ -13,7 +13,7 @@ env:
 
 jobs:
   rustfmt:
-    name: rustfmt / nightly-2022-11-12
+    name: rustfmt / nightly-2023-06-22
     runs-on: ubuntu-latest
 
     steps:
@@ -22,7 +22,7 @@ jobs:
 
       - name: Install rust
         run: |
-          rustup default nightly-2022-11-12
+          rustup default nightly-2023-06-22
           rustup component add rustfmt
 
       - name: cargo fmt
@@ -75,8 +75,8 @@ jobs:
             rust: stable
           - name: beta
             rust: beta
-          - name: 1.60.0
+          - name: '1.70'
-            rust: 1.60.0
+            rust: '1.70'
 
     steps:
       - name: Checkout
@@ -113,7 +113,10 @@ jobs:
         run: sudo apt -y install python3-dkim
 
       - name: Work around early dependencies MSRV bump
-        run: cargo update -p async-global-executor --precise 2.0.4
+        run: |
+          cargo update -p anstyle --precise 1.0.2
+          cargo update -p clap --precise 4.3.24
+          cargo update -p clap_lex --precise 0.5.0
 
       - name: Test with no default features
         run: cargo test --no-default-features
@@ -122,10 +125,10 @@ jobs:
         run: cargo test
 
       - name: Test with all features (-native-tls)
-        run: cargo test --no-default-features --features async-std,async-std1,async-std1-rustls-tls,async-trait,base64,boring,boring-tls,builder,dkim,ed25519-dalek,email-encoding,fastrand,file-transport,file-transport-envelope,futures-io,futures-rustls,futures-util,hostname,httpdate,mime,mime03,nom,once_cell,pool,quoted_printable,rsa,rustls,rustls-native-certs,rustls-pemfile,rustls-tls,sendmail-transport,serde,serde_json,sha2,smtp-transport,socket2,tokio1,tokio1-boring-tls,tokio1-rustls-tls,tokio1_boring,tokio1_crate,tokio1_rustls,tracing,uuid,webpki-roots
+        run: cargo test --no-default-features --features async-std1,async-std1-rustls-tls,boring-tls,builder,dkim,file-transport,file-transport-envelope,hostname,mime03,pool,rustls-native-certs,rustls-tls,sendmail-transport,smtp-transport,tokio1,tokio1-boring-tls,tokio1-rustls-tls,tracing
   
       - name: Test with all features (-boring-tls)
-        run: cargo test --no-default-features --features async-std,async-std1,async-std1-rustls-tls,async-trait,base64,builder,dkim,ed25519-dalek,email-encoding,fastrand,file-transport,file-transport-envelope,futures-io,futures-rustls,futures-util,hostname,httpdate,mime,mime03,native-tls,nom,once_cell,pool,quoted_printable,rsa,rustls,rustls-native-certs,rustls-pemfile,rustls-tls,sendmail-transport,serde,serde_json,sha2,smtp-transport,socket2,tokio1,tokio1-native-tls,tokio1-rustls-tls,tokio1_crate,tokio1_native_tls_crate,tokio1_rustls,tracing,uuid,webpki-roots
+        run: cargo test --no-default-features --features async-std1,async-std1-rustls-tls,builder,dkim,file-transport,file-transport-envelope,hostname,mime03,native-tls,pool,rustls-native-certs,rustls-tls,sendmail-transport,smtp-transport,tokio1,tokio1-native-tls,tokio1-rustls-tls,tracing
 
 #  coverage:
 #    name: Coverage

.gitignore

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

CHANGELOG.md

@@ -1,3 +1,104 @@
+<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)
 
@@ -143,7 +244,7 @@ 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 = "0.10.3"
+version = "0.11.4"
 description = "Email client"
 readme = "README.md"
 homepage = "https://lettre.rs"
@@ -11,7 +11,7 @@ authors = ["Alexis Mousset <contact@amousset.me>", "Paolo Barbolini <paolo@paolo
 categories = ["email", "network-programming"]
 keywords = ["email", "smtp", "mailer", "message", "sendmail"]
 edition = "2021"
-rust-version = "1.60"
+rust-version = "1.70"
 
 [badges]
 is-it-maintained-issue-resolution = { repository = "lettre/lettre" }
@@ -19,16 +19,16 @@ is-it-maintained-open-issues = { repository = "lettre/lettre" }
 maintenance = { status = "actively-developed" }
 
 [dependencies]
-idna = "0.3"
+chumsky = "0.9"
-once_cell = { version = "1", optional = true }
+idna = "0.5"
 tracing = { version = "0.1.16", default-features = false, features = ["std"], optional = true } # feature
 
 # 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 = "0.4.6", optional = true }
+quoted_printable = { version = "0.5", optional = true }
-base64 = { version = "0.21", optional = true }
+base64 = { version = "0.22", optional = true }
 email-encoding = { version = "0.2", optional = true }
 
 # file transport
@@ -39,15 +39,17 @@ serde_json = { version = "1", optional = true }
 # smtp-transport
 nom = { version = "7", optional = true }
 hostname = { version = "0.3", optional = true } # feature
-socket2 = { version = "0.4.4", optional = true }
+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 = "0.2.5", optional = true } # feature
-rustls = { version = "0.20", features = ["dangerous_configuration"], optional = true }
+rustls = { version = "0.22.1", optional = true }
-rustls-pemfile = { version = "1", optional = true }
+rustls-pemfile = { version = "2", optional = true }
-rustls-native-certs = { version = "0.6.2", optional = true }
+rustls-native-certs = { version = "0.7", optional = true }
-webpki-roots = { version = "0.22", optional = true }
+webpki-roots = { version = "0.26", optional = true }
-boring = { version = "2.0.0", optional = true }
+boring = { version = "4", optional = true }
 
 # async
 futures-io = { version = "0.3.7", optional = true }
@@ -57,25 +59,25 @@ async-trait = { version = "0.1", optional = true }
 ## async-std
 async-std = { version = "1.8", optional = true }
 #async-native-tls = { version = "0.3.3", optional = true }
-futures-rustls = { version = "0.22", optional = true }
+futures-rustls = { version = "0.25", optional = true }
 
 ## tokio
 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 = "0.25", optional = true }
-tokio1_boring = { package = "tokio-boring", version = "2.1.4", optional = true }
+tokio1_boring = { package = "tokio-boring", version = "4", optional = true }
 
 ## dkim
 sha2 = { version = "0.10", optional = true, features = ["oid"] }
-rsa = { version = "0.8", optional = true }
+rsa = { version = "0.9", optional = true }
-ed25519-dalek = { version = "1.0.1", optional = true }
+ed25519-dalek = { version = "2", optional = true }
 
 # email formats
 email_address = { version = "0.2.1", default-features = false }
 
 [dev-dependencies]
 pretty_assertions = "1"
-criterion = "0.4"
+criterion = "0.5"
 tracing = { version = "0.1.16", default-features = false, features = ["std"] }
 tracing-subscriber = "0.3"
 glob = "0.3"
@@ -83,39 +85,43 @@ walkdir = "2"
 tokio1_crate = { package = "tokio", version = "1", features = ["macros", "rt-multi-thread"] }
 async-std = { version = "1.8", features = ["attributes"] }
 serde_json = "1"
-maud = "0.24"
+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", "fastrand", "quoted_printable", "email-encoding"]
+builder = ["dep:httpdate", "dep:mime", "dep:fastrand", "dep:quoted_printable", "dep:email-encoding"]
-mime03 = ["mime"]
+mime03 = ["dep:mime"]
 
 # transports
-file-transport = ["uuid", "tokio1_crate?/fs", "tokio1_crate?/io-util"]
+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 = ["tokio1_crate?/process", "tokio1_crate?/io-util", "async-std?/unstable"]
-smtp-transport = ["base64", "nom", "socket2", "once_cell", "tokio1_crate?/rt", "tokio1_crate?/time", "tokio1_crate?/net"]
+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-tls = ["dep:webpki-roots", "dep:rustls", "dep:rustls-pemfile"]
 
-boring-tls = ["boring"]
+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-native-tls = ["async-std1", "native-tls", "dep:async-native-tls"]
-async-std1-rustls-tls = ["async-std1", "rustls-tls", "futures-rustls"]
+async-std1-rustls-tls = ["async-std1", "rustls-tls", "dep:futures-rustls"]
-tokio1 = ["tokio1_crate", "async-trait", "futures-io", "futures-util"]
+tokio1 = ["dep:tokio1_crate", "dep:async-trait", "dep:futures-io", "dep:futures-util"]
-tokio1-native-tls = ["tokio1", "native-tls", "tokio1_native_tls_crate"]
+tokio1-native-tls = ["tokio1", "native-tls", "dep:tokio1_native_tls_crate"]
-tokio1-rustls-tls = ["tokio1", "rustls-tls", "tokio1_rustls"]
+tokio1-rustls-tls = ["tokio1", "rustls-tls", "dep:tokio1_rustls"]
-tokio1-boring-tls = ["tokio1", "boring-tls", "tokio1_boring"]
+tokio1-boring-tls = ["tokio1", "boring-tls", "dep:tokio1_boring"]
 
-dkim = ["base64", "sha2", "rsa", "ed25519-dalek"]
+dkim = ["dep:base64", "dep:sha2", "dep:rsa", "dep:ed25519-dalek"]
 
 [package.metadata.docs.rs]
 all-features = true

README.md

@@ -28,8 +28,8 @@
 </div>
 
 <div align="center">
-  <a href="https://deps.rs/crate/lettre/0.10.3">
+  <a href="https://deps.rs/crate/lettre/0.11.4">
-    <img src="https://deps.rs/crate/lettre/0.10.3/status.svg"
+    <img src="https://deps.rs/crate/lettre/0.11.4/status.svg"
       alt="dependency status" />
   </a>
 </div>
@@ -53,17 +53,17 @@ Lettre does not provide (for now):
 ## 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 1.60, but this could change at any time either from
+the minimum supported Rust version is 1.70, 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 1.60 or newer.
+This library requires Rust 1.70 or newer.
 To use this library, add the following to your `Cargo.toml`:
 
 ```toml
 [dependencies]
-lettre = "0.10"
+lettre = "0.11"
 ```
 
 ```rust,no_run
@@ -91,7 +91,7 @@ let mailer = SmtpTransport::relay("smtp.gmail.com")
 // 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:?}"),
 }
 ```
 

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);

src/address/types.rs

@@ -15,7 +15,7 @@ use idna::domain_to_ascii;
 ///
 /// 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
 ///
@@ -227,6 +227,7 @@ fn check_address(val: &str) -> Result<usize, AddressError> {
 }
 
 #[derive(Debug, PartialEq, Eq, Clone, Copy)]
+#[non_exhaustive]
 /// Errors in email addresses parsing
 pub enum AddressError {
     /// Missing domain or user
@@ -237,6 +238,8 @@ pub enum AddressError {
     InvalidUser,
     /// Invalid email domain
     InvalidDomain,
+    /// Invalid input found
+    InvalidInput,
 }
 
 impl Error for AddressError {}
@@ -248,6 +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"),
         }
     }
 }

src/executor.rs

@@ -134,7 +134,7 @@ impl Executor for Tokio1Executor {
         #[allow(clippy::match_single_binding)]
         let tls_parameters = match tls {
             #[cfg(any(feature = "tokio1-native-tls", feature = "tokio1-rustls-tls"))]
-            Tls::Wrapper(ref tls_parameters) => Some(tls_parameters.clone()),
+            Tls::Wrapper(tls_parameters) => Some(tls_parameters.clone()),
             _ => None,
         };
         #[allow(unused_mut)]
@@ -149,13 +149,13 @@ impl Executor for Tokio1Executor {
 
         #[cfg(any(feature = "tokio1-native-tls", feature = "tokio1-rustls-tls"))]
         match tls {
-            Tls::Opportunistic(ref tls_parameters) => {
+            Tls::Opportunistic(tls_parameters) => {
                 if conn.can_starttls() {
-                    conn.starttls(tls_parameters.clone(), hello_name).await?;
+                    conn = 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?;
+                conn = conn.starttls(tls_parameters.clone(), hello_name).await?;
             }
             _ => (),
         }
@@ -216,7 +216,7 @@ impl Executor for AsyncStd1Executor {
 
     #[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)
     }
 
@@ -231,7 +231,7 @@ impl Executor for AsyncStd1Executor {
         #[allow(clippy::match_single_binding)]
         let tls_parameters = match tls {
             #[cfg(any(feature = "async-std1-native-tls", feature = "async-std1-rustls-tls"))]
-            Tls::Wrapper(ref tls_parameters) => Some(tls_parameters.clone()),
+            Tls::Wrapper(tls_parameters) => Some(tls_parameters.clone()),
             _ => None,
         };
         #[allow(unused_mut)]
@@ -245,13 +245,13 @@ impl Executor for AsyncStd1Executor {
 
         #[cfg(any(feature = "async-std1-native-tls", feature = "async-std1-rustls-tls"))]
         match tls {
-            Tls::Opportunistic(ref tls_parameters) => {
+            Tls::Opportunistic(tls_parameters) => {
                 if conn.can_starttls() {
-                    conn.starttls(tls_parameters.clone(), hello_name).await?;
+                    conn = 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?;
+                conn = conn.starttls(tls_parameters.clone(), hello_name).await?;
             }
             _ => (),
         }

src/lib.rs

@@ -6,7 +6,7 @@
 //! * Secure defaults
 //! * Async support
 //!
-//! Lettre requires Rust 1.60 or newer.
+//! Lettre requires Rust 1.70 or newer.
 //!
 //! ## Features
 //!
@@ -109,7 +109,7 @@
 //! [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/0.10.3")]
+#![doc(html_root_url = "https://docs.rs/crate/lettre/0.11.4")]
 #![doc(html_favicon_url = "https://lettre.rs/favicon.ico")]
 #![doc(html_logo_url = "https://avatars0.githubusercontent.com/u/15113230?v=4")]
 #![forbid(unsafe_code)]
@@ -219,11 +219,11 @@ 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;

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),
 }
 

src/message/body.rs

@@ -496,7 +496,7 @@ mod test {
     #[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

@@ -2,7 +2,6 @@ use std::{
     borrow::Cow,
     error::Error as StdError,
     fmt::{self, Display},
-    iter::IntoIterator,
     time::SystemTime,
 };
 
@@ -108,7 +107,7 @@ pub struct DkimSigningKey(InnerDkimSigningKey);
 #[derive(Debug)]
 enum InnerDkimSigningKey {
     Rsa(RsaPrivateKey),
-    Ed25519(ed25519_dalek::Keypair),
+    Ed25519(ed25519_dalek::SigningKey),
 }
 
 impl DkimSigningKey {
@@ -121,14 +120,18 @@ impl DkimSigningKey {
                 RsaPrivateKey::from_pkcs1_pem(private_key)
                     .map_err(|err| DkimSigningKeyError(InnerDkimSigningKeyError::Rsa(err)))?,
             ),
-            DkimSigningAlgorithm::Ed25519 => InnerDkimSigningKey::Ed25519(
+            DkimSigningAlgorithm::Ed25519 => {
-                ed25519_dalek::Keypair::from_bytes(
+                InnerDkimSigningKey::Ed25519(ed25519_dalek::SigningKey::from_bytes(
-                    &crate::base64::decode(private_key).map_err(|err| {
+                    &crate::base64::decode(private_key)
-                        DkimSigningKeyError(InnerDkimSigningKeyError::Base64(err))
+                        .map_err(|err| DkimSigningKeyError(InnerDkimSigningKeyError::Base64(err)))?
+                        .try_into()
+                        .map_err(|_| {
+                            DkimSigningKeyError(InnerDkimSigningKeyError::Ed25519(
+                                ed25519_dalek::ed25519::Error::new(),
+                            ))
                         })?,
-                )
+                ))
-                .map_err(|err| DkimSigningKeyError(InnerDkimSigningKeyError::Ed25519(err)))?,
+            }
-            ),
         }))
     }
     fn get_signing_algorithm(&self) -> DkimSigningAlgorithm {
@@ -140,19 +143,18 @@ impl DkimSigningKey {
 }
 
 /// A struct to describe Dkim configuration applied when signing a message
-/// selector: the name of the key publied in DNS
-/// domain: the domain for which we sign the message
-/// private_key: private key in PKCS1 string format
-/// headers: a list of headers name to be included in the signature. Signing of more than one
-/// header with same name is not supported
-/// canonicalization: the canonicalization to be applied on the message
-/// pub signing_algorithm: the signing algorithm to be used when signing
 #[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,
 }
 
@@ -341,7 +343,7 @@ fn dkim_canonicalize_headers<'a>(
     }
 }
 
-/// Sign with Dkim a message by adding Dkim-Signture header created with configuration expressed by
+/// 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) {

src/message/header/content.rs

@@ -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,
@@ -67,12 +69,6 @@ impl FromStr for ContentTransferEncoding {
     }
 }
 
-impl Default for ContentTransferEncoding {
-    fn default() -> Self {
-        ContentTransferEncoding::Base64
-    }
-}
-
 #[cfg(test)]
 mod test {
     use pretty_assertions::assert_eq;

src/message/header/content_disposition.rs

@@ -22,7 +22,7 @@ impl ContentDisposition {
     }
 
     /// 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 {
         Self::with_name("inline", file_name)
     }

src/message/header/content_type.rs

@@ -11,12 +11,12 @@ 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);
 

src/message/header/mailbox.rs

@@ -306,14 +306,30 @@ mod test {
     #[test]
     fn parse_multi_with_name_containing_comma() {
         let from: Vec<Mailbox> = vec![
-            "Test, test <1@example.com>".parse().unwrap(),
+            "\"Test, test\" <1@example.com>".parse().unwrap(),
-            "Test2, test2 <2@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(),
+            "\"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())));
@@ -324,9 +340,20 @@ mod test {
         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(),
+            "\"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

@@ -66,7 +66,7 @@ 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> {
@@ -310,7 +310,7 @@ impl HeaderValue {
     /// acceptable for use if `encoded_value` contains only ascii
     /// printable characters and is already line folded.
     ///
-    /// When in doubt use [`HeaderValue::new`].
+    /// When in doubt, use [`HeaderValue::new`].
     pub fn dangerous_new_pre_encoded(
         name: HeaderName,
         raw_value: String,

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 +1,248 @@
+//! 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 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 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 fn dot_atom() -> impl Parser<char, Vec<char>, Error = Cheap<char>> {
+    cfws().chain(dot_atom_text())
+}
+
+// dot-atom-text   =       1*atext *("." 1*atext)
+pub 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)))).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 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 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 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 fn obs_local_part() -> impl Parser<char, Vec<char>, Error = Cheap<char>> {
+    word().chain(just('.').chain(word()).repeated().flatten())
+}
+
+// obs-domain      =       atom *("." atom)
+pub 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

@@ -179,7 +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());
     }
@@ -198,7 +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()
         );
@@ -211,7 +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

@@ -5,15 +5,17 @@ use std::{
     str::FromStr,
 };
 
+use chumsky::prelude::*;
 use email_encoding::headers::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
 ///
@@ -86,7 +88,7 @@ impl Mailbox {
 
 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() {
                 write_word(f, name)?;
@@ -108,40 +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)
     }
 }
 
@@ -149,7 +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>);
 
@@ -356,34 +342,16 @@ impl Display for Mailboxes {
 impl FromStr for Mailboxes {
     type Err = AddressError;
 
-    fn from_str(mut src: &str) -> Result<Self, Self::Err> {
+    fn from_str(src: &str) -> Result<Self, Self::Err> {
         let mut mailboxes = Vec::new();
 
-        if !src.is_empty() {
+        let parsed_mailboxes = parsers::mailbox_list().parse(src).map_err(|_errs| {
-            // n-1 elements
+            // TODO: improve error management
-            let mut skip = 0;
+            AddressError::InvalidInput
-            while let Some(i) = src[skip..].find(',') {
+        })?;
-                let left = &src[..skip + i];
 
-                match left.trim().parse() {
+        for (name, (user, domain)) in parsed_mailboxes {
-                    Ok(mailbox) => {
+            mailboxes.push(Mailbox::new(name, Address::new(user, domain)?))
-                        mailboxes.push(mailbox);
-
-                        src = &src[left.len() + ",".len()..];
-                        skip = 0;
-                    }
-                    Err(AddressError::MissingParts) => {
-                        skip = left.len() + ",".len();
-                    }
-                    Err(err) => {
-                        return Err(err);
-                    }
-                }
-            }
-
-            // last element
-            let mailbox = src.trim().parse()?;
-            mailboxes.push(mailbox);
         }
 
         Ok(Mailboxes(mailboxes))
@@ -436,7 +404,7 @@ fn is_valid_atom_char(c: u8) -> bool {
 		b'}' |
 		b'~' |
 
-		// Not techically allowed but will be escaped into allowed characters.
+		// Not technically allowed but will be escaped into allowed characters.
 		128..=255)
 }
 

src/message/mimebody.rs

@@ -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
@@ -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 {
@@ -396,6 +406,15 @@ 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;

src/message/mod.rs

@@ -388,13 +388,13 @@ impl MessageBuilder {
 
     /// Keep the `Bcc` header
     ///
-    /// By default the `Bcc` header is removed from the email after
+    /// 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 behaviour.
+    /// Calling this method overrides the default behavior.
     pub fn keep_bcc(mut self) -> Self {
         self.drop_bcc = false;
         self
@@ -503,6 +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
@@ -520,7 +525,7 @@ impl Message {
     pub(crate) fn body_raw(&self) -> Vec<u8> {
         let mut out = Vec::new();
         match &self.body {
-            MessageBody::Mime(p) => p.format(&mut out),
+            MessageBody::Mime(p) => p.format_body(&mut out),
             MessageBody::Raw(r) => out.extend_from_slice(r),
         };
         out.extend_from_slice(b"\r\n");
@@ -630,7 +635,7 @@ 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())

src/transport/file/error.rs

@@ -54,7 +54,7 @@ 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);
         }
 
@@ -70,7 +70,7 @@ impl fmt::Display for Error {
             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}")?;
         }
 

src/transport/file/mod.rs

@@ -157,7 +157,7 @@ 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 {
@@ -167,7 +167,7 @@ pub struct FileTransport {
 }
 
 /// Asynchronously 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(any(feature = "tokio1", feature = "async-std1"))))]
 #[cfg(any(feature = "async-std1", feature = "tokio1"))]

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
 //!
@@ -75,7 +75,7 @@
 //! // 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(())
 //! # }
@@ -97,6 +97,7 @@
 //! [`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;

src/transport/sendmail/error.rs

@@ -52,7 +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);
         }
 
@@ -67,7 +67,7 @@ impl fmt::Display for 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}")?;
         }
 

src/transport/smtp/async_transport.rs

@@ -103,7 +103,7 @@ 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.
@@ -151,28 +151,114 @@ 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 and port can be provided in a single URL.
+    /// Use the scheme `smtp` for an unencrypted relay (optionally in combination with the
+    /// `tls` parameter to allow/require STARTTLS) or `smtps` for SMTP over TLS.
+    /// The path section of the url can be used to set an alternative name for
+    /// the HELO / EHLO command.
+    /// For example `smtps://username:password@smtp.example.com/client.example.com:465`
+    /// will set the HELO / EHLO name `client.example.com`.
+    ///
+    /// <table>
+    ///   <thead>
+    ///     <tr>
+    ///       <th>scheme</th>
+    ///       <th>tls parameter</th>
+    ///       <th>example</th>
+    ///       <th>remarks</th>
+    ///     </tr>
+    ///   </thead>
+    ///   <tbody>
+    ///     <tr>
+    ///      <td>smtps</td>
+    ///      <td>-</td>
+    ///      <td>smtps://smtp.example.com</td>
+    ///      <td>SMTP over TLS, recommended method</td>
+    ///     </tr>
+    ///     <tr>
+    ///      <td>smtp</td>
+    ///      <td>required</td>
+    ///      <td>smtp://smtp.example.com?tls=required</td>
+    ///      <td>SMTP with STARTTLS required, when SMTP over TLS is not available</td>
+    ///     </tr>
+    ///     <tr>
+    ///      <td>smtp</td>
+    ///      <td>opportunistic</td>
+    ///      <td>smtp://smtp.example.com?tls=opportunistic</td>
+    ///      <td>
+    ///         SMTP with optionally STARTTLS when supported by the server.
+    ///         Caution: this method is vulnerable to a man-in-the-middle attack.
+    ///         Not recommended for production use.
+    ///       </td>
+    ///     </tr>
+    ///     <tr>
+    ///      <td>smtp</td>
+    ///      <td>-</td>
+    ///      <td>smtp://smtp.example.com</td>
+    ///      <td>Unencrypted SMTP, not recommended for production use.</td>
+    ///     </tr>
+    ///   </tbody>
+    /// </table>
+    ///
+    /// ```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",
+    ///     )
+    ///     .unwrap()
+    ///     .build();
+    ///
+    /// // Send the email
+    /// match mailer.send(email).await {
+    ///     Ok(_) => println!("Email sent successfully!"),
+    ///     Err(e) => panic!("Could not send email: {e:?}"),
+    /// }
+    /// # Ok(())
+    /// # }
+    /// ```
+    #[cfg(any(feature = "native-tls", feature = "rustls-tls", feature = "boring-tls"))]
+    #[cfg_attr(
+        docsrs,
+        doc(cfg(any(feature = "native-tls", feature = "rustls-tls", 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?;
 
@@ -219,6 +305,20 @@ 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;

src/transport/smtp/authentication.rs

@@ -51,7 +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,
@@ -71,7 +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,
@@ -98,11 +98,13 @@ impl Mechanism {
                 let decoded_challenge = challenge
                     .ok_or_else(|| error::client("This mechanism does expect a challenge"))?;
 
-                if ["User Name", "Username:", "Username"].contains(&decoded_challenge) {
+                if ["User Name", "Username:", "Username", "User Name\0"]
+                    .contains(&decoded_challenge)
+                {
                     return Ok(credentials.authentication_identity.clone());
                 }
 
-                if ["Password", "Password:"].contains(&decoded_challenge) {
+                if ["Password", "Password:", "Password\0"].contains(&decoded_challenge) {
                     return Ok(credentials.secret.clone());
                 }
 

src/transport/smtp/client/async_connection.rs

@@ -6,7 +6,7 @@ use futures_util::io::{AsyncBufReadExt, AsyncWriteExt, BufReader};
 use super::async_net::AsyncTokioStream;
 #[cfg(feature = "tracing")]
 use super::escape_crlf;
-use super::{AsyncNetworkStream, ClientCodec, TlsParameters};
+use super::{AsyncNetworkStream, ClientCodec, ConnectionState, TlsParameters};
 use crate::{
     transport::smtp::{
         authentication::{Credentials, Mechanism},
@@ -19,25 +19,11 @@ use crate::{
     Envelope,
 };
 
-macro_rules! try_smtp (
-    ($err: expr, $client: ident) => ({
-        match $err {
-            Ok(val) => val,
-            Err(err) => {
-                $client.abort().await;
-                return Err(From::from(err))
-            },
-        }
-    })
-);
-
 /// Structure that implements the SMTP client
 pub struct AsyncSmtpConnection {
     /// TCP stream between client and server
     /// Value is None before connection
     stream: BufReader<AsyncNetworkStream>,
-    /// Panic state
-    panic: bool,
     /// Information about the server
     server_info: ServerInfo,
 }
@@ -62,7 +48,35 @@ impl AsyncSmtpConnection {
 
     /// 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
+    /// .unwrap();
+    /// # Ok(())
+    /// # }
+    /// ```
     #[cfg(feature = "tokio1")]
     pub async fn connect_tokio1<T: tokio1_crate::net::ToSocketAddrs>(
         server: T,
@@ -98,7 +112,6 @@ impl AsyncSmtpConnection {
         let stream = BufReader::new(stream);
         let mut conn = AsyncSmtpConnection {
             stream,
-            panic: false,
             server_info: ServerInfo::default(),
         };
         // TODO log
@@ -132,7 +145,7 @@ 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(
@@ -142,50 +155,54 @@ impl AsyncSmtpConnection {
             mail_options.push(MailParameter::Body(MailBodyParameter::EightBitMime));
         }
 
-        try_smtp!(
         self.command(Mail::new(envelope.from().cloned(), mail_options))
-                .await,
+            .await?;
-            self
-        );
 
         // Recipient
         for to_address in envelope.to() {
-            try_smtp!(
+            self.command(Rcpt::new(to_address.clone(), vec![])).await?;
-                self.command(Rcpt::new(to_address.clone(), vec![])).await,
-                self
-            );
         }
 
         // Data
-        try_smtp!(self.command(Data).await, self);
+        self.command(Data).await?;
 
         // Message content
-        let result = try_smtp!(self.message(email).await, self);
+        self.message(email).await
-        Ok(result)
     }
 
     pub fn has_broken(&self) -> bool {
-        self.panic
+        match self.stream.get_ref().state() {
+            ConnectionState::Ok => false,
+            ConnectionState::Broken | ConnectionState::Closed => true,
+        }
     }
 
     pub fn can_starttls(&self) -> bool {
         !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,
+        mut self,
         tls_parameters: TlsParameters,
         hello_name: &ClientId,
-    ) -> Result<(), Error> {
+    ) -> Result<Self, Error> {
         if self.server_info.supports_feature(Extension::StartTls) {
-            try_smtp!(self.command(Starttls).await, self);
+            self.command(Starttls).await?;
-            self.stream.get_mut().upgrade_tls(tls_parameters).await?;
+            let stream = self.stream.into_inner();
+            let stream = stream.upgrade_tls(tls_parameters).await?;
+            self.stream = BufReader::new(stream);
             #[cfg(feature = "tracing")]
             tracing::debug!("connection encrypted");
             // Send EHLO again
-            try_smtp!(self.ehlo(hello_name).await, self);
+            self.ehlo(hello_name).await?;
-            Ok(())
+            Ok(self)
         } else {
             Err(error::client("STARTTLS is not supported on this server"))
         }
@@ -193,22 +210,24 @@ impl AsyncSmtpConnection {
 
     /// Send EHLO and update server info
     async fn ehlo(&mut self, hello_name: &ClientId) -> Result<(), Error> {
-        let ehlo_response = try_smtp!(self.command(Ehlo::new(hello_name.clone())).await, self);
+        let ehlo_response = self.command(Ehlo::new(hello_name.clone())).await?;
-        self.server_info = try_smtp!(ServerInfo::from_response(&ehlo_response), self);
+        self.server_info = ServerInfo::from_response(&ehlo_response)?;
         Ok(())
     }
 
     pub async fn quit(&mut self) -> Result<Response, Error> {
-        Ok(try_smtp!(self.command(Quit).await, self))
+        self.command(Quit).await
     }
 
     pub async fn abort(&mut self) {
-        // Only try to quit if we are not already broken
+        match self.stream.get_ref().state() {
-        if !self.panic {
+            ConnectionState::Ok | ConnectionState::Broken => {
-            self.panic = true;
                 let _ = self.command(Quit).await;
-        }
                 let _ = self.stream.close().await;
+                self.stream.get_mut().set_state(ConnectionState::Closed);
+            }
+            ConnectionState::Closed => {}
+        }
     }
 
     /// Sets the underlying stream
@@ -226,7 +245,7 @@ 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],
@@ -245,15 +264,13 @@ impl AsyncSmtpConnection {
 
         while challenges > 0 && response.has_code(334) {
             challenges -= 1;
-            response = try_smtp!(
+            response = self
-                self.command(Auth::new_from_response(
+                .command(Auth::new_from_response(
                     mechanism,
                     credentials.clone(),
                     &response,
                 )?)
-                .await,
+                .await?;
-                self
-            );
         }
 
         if challenges == 0 {
@@ -281,6 +298,9 @@ impl AsyncSmtpConnection {
 
     /// Writes a string to the server
     async fn write(&mut self, string: &[u8]) -> Result<(), Error> {
+        self.stream.get_ref().state().verify()?;
+        self.stream.get_mut().set_state(ConnectionState::Broken);
+
         self.stream
             .get_mut()
             .write_all(string)
@@ -292,6 +312,8 @@ impl AsyncSmtpConnection {
             .await
             .map_err(error::network)?;
 
+        self.stream.get_mut().set_state(ConnectionState::Ok);
+
         #[cfg(feature = "tracing")]
         tracing::debug!("Wrote: {}", escape_crlf(&String::from_utf8_lossy(string)));
         Ok(())
@@ -299,6 +321,9 @@ impl AsyncSmtpConnection {
 
     /// Gets the SMTP response
     pub async fn read_response(&mut self) -> Result<Response, Error> {
+        self.stream.get_ref().state().verify()?;
+        self.stream.get_mut().set_state(ConnectionState::Broken);
+
         let mut buffer = String::with_capacity(100);
 
         while self
@@ -312,6 +337,8 @@ impl AsyncSmtpConnection {
             tracing::debug!("<< {}", escape_crlf(&buffer));
             match parse_response(&buffer) {
                 Ok((_remaining, response)) => {
+                    self.stream.get_mut().set_state(ConnectionState::Ok);
+
                     return if response.is_positive() {
                         Ok(response)
                     } else {
@@ -319,7 +346,7 @@ impl AsyncSmtpConnection {
                             response.code(),
                             Some(response.message().collect()),
                         ))
-                    }
+                    };
                 }
                 Err(nom::Err::Failure(e)) => {
                     return Err(error::response(e.to_string()));

src/transport/smtp/client/async_net.rs

@@ -11,11 +11,12 @@ use async_native_tls::TlsStream as AsyncStd1TlsStream;
 #[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, ErrorKind,
+    AsyncRead as FuturesAsyncRead, AsyncWrite as FuturesAsyncWrite, Result as IoResult,
-    Result as IoResult,
 };
 #[cfg(feature = "async-std1-rustls-tls")]
 use futures_rustls::client::TlsStream as AsyncStd1RustlsTlsStream;
+#[cfg(any(feature = "tokio1-rustls-tls", feature = "async-std1-rustls-tls"))]
+use rustls::pki_types::ServerName;
 #[cfg(feature = "tokio1-boring-tls")]
 use tokio1_boring::SslStream as Tokio1SslStream;
 #[cfg(feature = "tokio1")]
@@ -38,7 +39,7 @@ use tokio1_rustls::client::TlsStream as Tokio1RustlsTlsStream;
     feature = "async-std1-rustls-tls"
 ))]
 use super::InnerTlsParameters;
-use super::TlsParameters;
+use super::{ConnectionState, TlsParameters};
 #[cfg(feature = "tokio1")]
 use crate::transport::smtp::client::net::resolved_address_filter;
 use crate::transport::smtp::{error, Error};
@@ -47,6 +48,7 @@ use crate::transport::smtp::{error, Error};
 #[derive(Debug)]
 pub struct AsyncNetworkStream {
     inner: InnerAsyncNetworkStream,
+    state: ConnectionState,
 }
 
 #[cfg(feature = "tokio1")]
@@ -89,45 +91,43 @@ enum InnerAsyncNetworkStream {
     /// Encrypted Tokio 1.x TCP stream
     #[cfg(feature = "async-std1-rustls-tls")]
     AsyncStd1RustlsTls(AsyncStd1RustlsTlsStream<AsyncStd1TcpStream>),
-    /// Can't be built
-    None,
 }
 
 impl AsyncNetworkStream {
     fn new(inner: InnerAsyncNetworkStream) -> Self {
-        if let InnerAsyncNetworkStream::None = inner {
+        AsyncNetworkStream {
-            debug_assert!(false, "InnerAsyncNetworkStream::None must never be built");
+            inner,
+            state: ConnectionState::Ok,
+        }
     }
 
-        AsyncNetworkStream { inner }
+    pub(super) fn state(&self) -> ConnectionState {
+        self.state
+    }
+
+    pub(super) fn set_state(&mut self, state: ConnectionState) {
+        self.state = state;
     }
 
     /// 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")]
-            InnerAsyncNetworkStream::Tokio1RustlsTls(ref s) => s.get_ref().0.peer_addr(),
+            InnerAsyncNetworkStream::Tokio1RustlsTls(s) => s.get_ref().0.peer_addr(),
             #[cfg(feature = "tokio1-boring-tls")]
-            InnerAsyncNetworkStream::Tokio1BoringTls(ref s) => s.get_ref().peer_addr(),
+            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")]
-            InnerAsyncNetworkStream::AsyncStd1NativeTls(ref s) => s.get_ref().peer_addr(),
+            InnerAsyncNetworkStream::AsyncStd1NativeTls(s) => s.get_ref().peer_addr(),
             #[cfg(feature = "async-std1-rustls-tls")]
-            InnerAsyncNetworkStream::AsyncStd1RustlsTls(ref s) => s.get_ref().0.peer_addr(),
+            InnerAsyncNetworkStream::AsyncStd1RustlsTls(s) => s.get_ref().0.peer_addr(),
-            InnerAsyncNetworkStream::None => {
-                debug_assert!(false, "InnerAsyncNetworkStream::None must never be built");
-                Err(IoError::new(
-                    ErrorKind::Other,
-                    "InnerAsyncNetworkStream::None must never be built",
-                ))
-            }
         }
     }
 
@@ -197,7 +197,7 @@ impl AsyncNetworkStream {
         let mut stream =
             AsyncNetworkStream::new(InnerAsyncNetworkStream::Tokio1Tcp(Box::new(tcp_stream)));
         if let Some(tls_parameters) = tls_parameters {
-            stream.upgrade_tls(tls_parameters).await?;
+            stream = stream.upgrade_tls(tls_parameters).await?;
         }
         Ok(stream)
     }
@@ -208,9 +208,9 @@ impl AsyncNetworkStream {
         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
+        // 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
-        // connected which is a blocking operation.
+        // been connected, which is a blocking operation.
         async fn try_connect_timeout<T: AsyncStd1ToSocketAddrs>(
             server: T,
             timeout: Duration,
@@ -248,13 +248,13 @@ impl AsyncNetworkStream {
 
         let mut stream = AsyncNetworkStream::new(InnerAsyncNetworkStream::AsyncStd1Tcp(tcp_stream));
         if let Some(tls_parameters) = tls_parameters {
-            stream.upgrade_tls(tls_parameters).await?;
+            stream = stream.upgrade_tls(tls_parameters).await?;
         }
         Ok(stream)
     }
 
-    pub async fn upgrade_tls(&mut self, tls_parameters: TlsParameters) -> Result<(), Error> {
+    pub async fn upgrade_tls(self, tls_parameters: TlsParameters) -> Result<Self, Error> {
-        match &self.inner {
+        match self.inner {
             #[cfg(all(
                 feature = "tokio1",
                 not(any(
@@ -273,18 +273,14 @@ impl AsyncNetworkStream {
                 feature = "tokio1-rustls-tls",
                 feature = "tokio1-boring-tls"
             ))]
-            InnerAsyncNetworkStream::Tokio1Tcp(_) => {
+            InnerAsyncNetworkStream::Tokio1Tcp(tcp_stream) => {
-                // get owned TcpStream
+                let inner = Self::upgrade_tokio1_tls(tcp_stream, tls_parameters)
-                let tcp_stream = mem::replace(&mut self.inner, InnerAsyncNetworkStream::None);
-                let tcp_stream = match tcp_stream {
-                    InnerAsyncNetworkStream::Tokio1Tcp(tcp_stream) => tcp_stream,
-                    _ => unreachable!(),
-                };
-
-                self.inner = Self::upgrade_tokio1_tls(tcp_stream, tls_parameters)
                     .await
                     .map_err(error::connection)?;
-                Ok(())
+                Ok(Self {
+                    inner,
+                    state: ConnectionState::Ok,
+                })
             }
             #[cfg(all(
                 feature = "async-std1",
@@ -296,20 +292,16 @@ impl AsyncNetworkStream {
             }
 
             #[cfg(any(feature = "async-std1-native-tls", feature = "async-std1-rustls-tls"))]
-            InnerAsyncNetworkStream::AsyncStd1Tcp(_) => {
+            InnerAsyncNetworkStream::AsyncStd1Tcp(tcp_stream) => {
-                // get owned TcpStream
+                let inner = Self::upgrade_asyncstd1_tls(tcp_stream, tls_parameters)
-                let tcp_stream = mem::replace(&mut self.inner, InnerAsyncNetworkStream::None);
-                let tcp_stream = match tcp_stream {
-                    InnerAsyncNetworkStream::AsyncStd1Tcp(tcp_stream) => tcp_stream,
-                    _ => unreachable!(),
-                };
-
-                self.inner = Self::upgrade_asyncstd1_tls(tcp_stream, tls_parameters)
                     .await
                     .map_err(error::connection)?;
-                Ok(())
+                Ok(Self {
+                    inner,
+                    state: ConnectionState::Ok,
+                })
             }
-            _ => Ok(()),
+            _ => Ok(self),
         }
     }
 
@@ -350,7 +342,6 @@ impl AsyncNetworkStream {
 
                 #[cfg(feature = "tokio1-rustls-tls")]
                 return {
-                    use rustls::ServerName;
                     use tokio1_rustls::TlsConnector;
 
                     let domain = ServerName::try_from(domain.as_str())
@@ -358,7 +349,7 @@ impl AsyncNetworkStream {
 
                     let connector = TlsConnector::from(config);
                     let stream = connector
-                        .connect(domain, tcp_stream)
+                        .connect(domain.to_owned(), tcp_stream)
                         .await
                         .map_err(error::connection)?;
                     Ok(InnerAsyncNetworkStream::Tokio1RustlsTls(stream))
@@ -424,14 +415,13 @@ impl AsyncNetworkStream {
                 #[cfg(feature = "async-std1-rustls-tls")]
                 return {
                     use futures_rustls::TlsConnector;
-                    use rustls::ServerName;
 
                     let domain = ServerName::try_from(domain.as_str())
                         .map_err(|_| error::connection("domain isn't a valid DNS name"))?;
 
                     let connector = TlsConnector::from(config);
                     let stream = connector
-                        .connect(domain, tcp_stream)
+                        .connect(domain.to_owned(), tcp_stream)
                         .await
                         .map_err(error::connection)?;
                     Ok(InnerAsyncNetworkStream::AsyncStd1RustlsTls(stream))
@@ -445,7 +435,7 @@ impl AsyncNetworkStream {
     }
 
     pub fn is_encrypted(&self) -> bool {
-        match self.inner {
+        match &self.inner {
             #[cfg(feature = "tokio1")]
             InnerAsyncNetworkStream::Tokio1Tcp(_) => false,
             #[cfg(feature = "tokio1-native-tls")]
@@ -460,7 +450,6 @@ impl AsyncNetworkStream {
             InnerAsyncNetworkStream::AsyncStd1NativeTls(_) => true,
             #[cfg(feature = "async-std1-rustls-tls")]
             InnerAsyncNetworkStream::AsyncStd1RustlsTls(_) => true,
-            InnerAsyncNetworkStream::None => false,
         }
     }
 
@@ -486,8 +475,7 @@ impl AsyncNetworkStream {
                 .unwrap()
                 .first()
                 .unwrap()
-                .clone()
+                .to_vec()),
-                .0),
             #[cfg(feature = "tokio1-boring-tls")]
             InnerAsyncNetworkStream::Tokio1BoringTls(stream) => Ok(stream
                 .ssl()
@@ -509,9 +497,7 @@ impl AsyncNetworkStream {
                 .unwrap()
                 .first()
                 .unwrap()
-                .clone()
+                .to_vec()),
-                .0),
-            InnerAsyncNetworkStream::None => panic!("InnerNetworkStream::None must never be built"),
         }
     }
 }
@@ -522,9 +508,9 @@ impl FuturesAsyncRead for AsyncNetworkStream {
         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())),
@@ -533,7 +519,7 @@ 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())),
@@ -542,7 +528,7 @@ impl FuturesAsyncRead for AsyncNetworkStream {
                 }
             }
             #[cfg(feature = "tokio1-rustls-tls")]
-            InnerAsyncNetworkStream::Tokio1RustlsTls(ref mut s) => {
+            InnerAsyncNetworkStream::Tokio1RustlsTls(s) => {
                 let mut b = Tokio1ReadBuf::new(buf);
                 match Pin::new(s).poll_read(cx, &mut b) {
                     Poll::Ready(Ok(())) => Poll::Ready(Ok(b.filled().len())),
@@ -551,7 +537,7 @@ impl FuturesAsyncRead for AsyncNetworkStream {
                 }
             }
             #[cfg(feature = "tokio1-boring-tls")]
-            InnerAsyncNetworkStream::Tokio1BoringTls(ref mut s) => {
+            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())),
@@ -560,19 +546,11 @@ 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")]
-            InnerAsyncNetworkStream::AsyncStd1NativeTls(ref mut s) => {
+            InnerAsyncNetworkStream::AsyncStd1NativeTls(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) => {
+            InnerAsyncNetworkStream::AsyncStd1RustlsTls(s) => Pin::new(s).poll_read(cx, buf),
-                Pin::new(s).poll_read(cx, buf)
-            }
-            InnerAsyncNetworkStream::None => {
-                debug_assert!(false, "InnerAsyncNetworkStream::None must never be built");
-                Poll::Ready(Ok(0))
-            }
         }
     }
 }
@@ -583,75 +561,61 @@ impl FuturesAsyncWrite for AsyncNetworkStream {
         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")]
-            InnerAsyncNetworkStream::Tokio1RustlsTls(ref mut s) => Pin::new(s).poll_write(cx, buf),
+            InnerAsyncNetworkStream::Tokio1RustlsTls(s) => Pin::new(s).poll_write(cx, buf),
             #[cfg(feature = "tokio1-boring-tls")]
-            InnerAsyncNetworkStream::Tokio1BoringTls(ref mut s) => Pin::new(s).poll_write(cx, buf),
+            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")]
-            InnerAsyncNetworkStream::AsyncStd1NativeTls(ref mut s) => {
+            InnerAsyncNetworkStream::AsyncStd1NativeTls(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) => {
+            InnerAsyncNetworkStream::AsyncStd1RustlsTls(s) => Pin::new(s).poll_write(cx, buf),
-                Pin::new(s).poll_write(cx, buf)
-            }
-            InnerAsyncNetworkStream::None => {
-                debug_assert!(false, "InnerAsyncNetworkStream::None must never be built");
-                Poll::Ready(Ok(0))
-            }
         }
     }
 
     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")]
-            InnerAsyncNetworkStream::Tokio1RustlsTls(ref mut s) => Pin::new(s).poll_flush(cx),
+            InnerAsyncNetworkStream::Tokio1RustlsTls(s) => Pin::new(s).poll_flush(cx),
             #[cfg(feature = "tokio1-boring-tls")]
-            InnerAsyncNetworkStream::Tokio1BoringTls(ref mut s) => Pin::new(s).poll_flush(cx),
+            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")]
-            InnerAsyncNetworkStream::AsyncStd1NativeTls(ref mut s) => Pin::new(s).poll_flush(cx),
+            InnerAsyncNetworkStream::AsyncStd1NativeTls(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::AsyncStd1RustlsTls(s) => Pin::new(s).poll_flush(cx),
-            InnerAsyncNetworkStream::None => {
-                debug_assert!(false, "InnerAsyncNetworkStream::None must never be built");
-                Poll::Ready(Ok(()))
-            }
         }
     }
 
     fn poll_close(mut self: Pin<&mut Self>, cx: &mut Context<'_>) -> Poll<IoResult<()>> {
-        match self.inner {
+        self.state = ConnectionState::Closed;
+
+        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")]
-            InnerAsyncNetworkStream::Tokio1RustlsTls(ref mut s) => Pin::new(s).poll_shutdown(cx),
+            InnerAsyncNetworkStream::Tokio1RustlsTls(s) => Pin::new(s).poll_shutdown(cx),
             #[cfg(feature = "tokio1-boring-tls")]
-            InnerAsyncNetworkStream::Tokio1BoringTls(ref mut s) => Pin::new(s).poll_shutdown(cx),
+            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")]
-            InnerAsyncNetworkStream::AsyncStd1NativeTls(ref mut s) => Pin::new(s).poll_close(cx),
+            InnerAsyncNetworkStream::AsyncStd1NativeTls(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::AsyncStd1RustlsTls(s) => Pin::new(s).poll_close(cx),
-            InnerAsyncNetworkStream::None => {
-                debug_assert!(false, "InnerAsyncNetworkStream::None must never be built");
-                Poll::Ready(Ok(()))
-            }
         }
     }
 }

src/transport/smtp/client/connection.rs

@@ -7,7 +7,7 @@ use std::{
 
 #[cfg(feature = "tracing")]
 use super::escape_crlf;
-use super::{ClientCodec, NetworkStream, TlsParameters};
+use super::{ClientCodec, ConnectionState, NetworkStream, TlsParameters};
 use crate::{
     address::Envelope,
     transport::smtp::{
@@ -20,25 +20,11 @@ use crate::{
     },
 };
 
-macro_rules! try_smtp (
-    ($err: expr, $client: ident) => ({
-        match $err {
-            Ok(val) => val,
-            Err(err) => {
-                $client.abort();
-                return Err(From::from(err))
-            },
-        }
-    })
-);
-
 /// Structure that implements the SMTP client
 pub struct SmtpConnection {
     /// TCP stream between client and server
     /// Value is None before connection
     stream: BufReader<NetworkStream>,
-    /// Panic state
-    panic: bool,
     /// Information about the server
     server_info: ServerInfo,
 }
@@ -65,7 +51,6 @@ impl SmtpConnection {
         let stream = BufReader::new(stream);
         let mut conn = SmtpConnection {
             stream,
-            panic: false,
             server_info: ServerInfo::default(),
         };
         conn.set_timeout(timeout).map_err(error::network)?;
@@ -100,7 +85,7 @@ 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(
@@ -110,26 +95,25 @@ impl SmtpConnection {
             mail_options.push(MailParameter::Body(MailBodyParameter::EightBitMime));
         }
 
-        try_smtp!(
+        self.command(Mail::new(envelope.from().cloned(), mail_options))?;
-            self.command(Mail::new(envelope.from().cloned(), mail_options)),
-            self
-        );
 
         // Recipient
         for to_address in envelope.to() {
-            try_smtp!(self.command(Rcpt::new(to_address.clone(), vec![])), self);
+            self.command(Rcpt::new(to_address.clone(), vec![]))?;
         }
 
         // Data
-        try_smtp!(self.command(Data), self);
+        self.command(Data)?;
 
         // Message content
-        let result = try_smtp!(self.message(email), self);
+        self.message(email)
-        Ok(result)
     }
 
     pub fn has_broken(&self) -> bool {
-        self.panic
+        match self.stream.get_ref().state() {
+            ConnectionState::Ok => false,
+            ConnectionState::Broken | ConnectionState::Closed => true,
+        }
     }
 
     pub fn can_starttls(&self) -> bool {
@@ -138,20 +122,22 @@ impl SmtpConnection {
 
     #[allow(unused_variables)]
     pub fn starttls(
-        &mut self,
+        mut self,
         tls_parameters: &TlsParameters,
         hello_name: &ClientId,
-    ) -> Result<(), Error> {
+    ) -> Result<Self, Error> {
         if self.server_info.supports_feature(Extension::StartTls) {
             #[cfg(any(feature = "native-tls", feature = "rustls-tls", feature = "boring-tls"))]
             {
-                try_smtp!(self.command(Starttls), self);
+                self.command(Starttls)?;
-                self.stream.get_mut().upgrade_tls(tls_parameters)?;
+                let stream = self.stream.into_inner();
+                let stream = stream.upgrade_tls(tls_parameters)?;
+                self.stream = BufReader::new(stream);
                 #[cfg(feature = "tracing")]
                 tracing::debug!("connection encrypted");
                 // Send EHLO again
-                try_smtp!(self.ehlo(hello_name), self);
+                self.ehlo(hello_name)?;
-                Ok(())
+                Ok(self)
             }
             #[cfg(not(any(
                 feature = "native-tls",
@@ -168,22 +154,24 @@ impl SmtpConnection {
 
     /// Send EHLO and update server info
     fn ehlo(&mut self, hello_name: &ClientId) -> Result<(), Error> {
-        let ehlo_response = try_smtp!(self.command(Ehlo::new(hello_name.clone())), self);
+        let ehlo_response = self.command(Ehlo::new(hello_name.clone()))?;
-        self.server_info = try_smtp!(ServerInfo::from_response(&ehlo_response), self);
+        self.server_info = ServerInfo::from_response(&ehlo_response)?;
         Ok(())
     }
 
     pub fn quit(&mut self) -> Result<Response, Error> {
-        Ok(try_smtp!(self.command(Quit), self))
+        self.command(Quit)
     }
 
     pub fn abort(&mut self) {
-        // Only try to quit if we are not already broken
+        match self.stream.get_ref().state() {
-        if !self.panic {
+            ConnectionState::Ok | ConnectionState::Broken => {
-            self.panic = true;
                 let _ = self.command(Quit);
-        }
                 let _ = self.stream.get_mut().shutdown(std::net::Shutdown::Both);
+                self.stream.get_mut().set_state(ConnectionState::Closed);
+            }
+            ConnectionState::Closed => {}
+        }
     }
 
     /// Sets the underlying stream
@@ -207,7 +195,7 @@ 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],
@@ -224,14 +212,11 @@ impl SmtpConnection {
 
         while challenges > 0 && response.has_code(334) {
             challenges -= 1;
-            response = try_smtp!(
+            response = self.command(Auth::new_from_response(
-                self.command(Auth::new_from_response(
                 mechanism,
                 credentials.clone(),
                 &response,
-                )?),
+            )?)?;
-                self
-            );
         }
 
         if challenges == 0 {
@@ -260,12 +245,17 @@ impl SmtpConnection {
 
     /// Writes a string to the server
     fn write(&mut self, string: &[u8]) -> Result<(), Error> {
+        self.stream.get_ref().state().verify()?;
+        self.stream.get_mut().set_state(ConnectionState::Broken);
+
         self.stream
             .get_mut()
             .write_all(string)
             .map_err(error::network)?;
         self.stream.get_mut().flush().map_err(error::network)?;
 
+        self.stream.get_mut().set_state(ConnectionState::Ok);
+
         #[cfg(feature = "tracing")]
         tracing::debug!("Wrote: {}", escape_crlf(&String::from_utf8_lossy(string)));
         Ok(())
@@ -273,6 +263,9 @@ impl SmtpConnection {
 
     /// Gets the SMTP response
     pub fn read_response(&mut self) -> Result<Response, Error> {
+        self.stream.get_ref().state().verify()?;
+        self.stream.get_mut().set_state(ConnectionState::Broken);
+
         let mut buffer = String::with_capacity(100);
 
         while self.stream.read_line(&mut buffer).map_err(error::network)? > 0 {
@@ -280,6 +273,8 @@ impl SmtpConnection {
             tracing::debug!("<< {}", escape_crlf(&buffer));
             match parse_response(&buffer) {
                 Ok((_remaining, response)) => {
+                    self.stream.get_mut().set_state(ConnectionState::Ok);
+
                     return if response.is_positive() {
                         Ok(response)
                     } else {

src/transport/smtp/client/mod.rs

@@ -40,6 +40,7 @@ pub use self::{
     connection::SmtpConnection,
     tls::{Certificate, CertificateStore, Tls, TlsParameters, TlsParametersBuilder},
 };
+use super::{error, Error};
 
 #[cfg(any(feature = "tokio1", feature = "async-std1"))]
 mod async_connection;
@@ -49,6 +50,23 @@ mod connection;
 mod net;
 mod tls;
 
+#[derive(Debug, Copy, Clone)]
+enum ConnectionState {
+    Ok,
+    Broken,
+    Closed,
+}
+
+impl ConnectionState {
+    fn verify(&mut self) -> Result<(), Error> {
+        match self {
+            Self::Ok => Ok(()),
+            Self::Broken => Err(error::connection("connection broken")),
+            Self::Closed => Err(error::connection("connection closed")),
+        }
+    }
+}
+
 /// The codec used for transparency
 #[derive(Debug)]
 struct ClientCodec {

src/transport/smtp/client/net.rs

@@ -2,8 +2,7 @@
 use std::sync::Arc;
 use std::{
     io::{self, Read, Write},
-    mem,
+    net::{IpAddr, Shutdown, SocketAddr, TcpStream, ToSocketAddrs},
-    net::{IpAddr, Ipv4Addr, Shutdown, SocketAddr, SocketAddrV4, TcpStream, ToSocketAddrs},
     time::Duration,
 };
 
@@ -12,17 +11,18 @@ use boring::ssl::SslStream;
 #[cfg(feature = "native-tls")]
 use native_tls::TlsStream;
 #[cfg(feature = "rustls-tls")]
-use rustls::{ClientConnection, ServerName, StreamOwned};
+use rustls::{pki_types::ServerName, ClientConnection, StreamOwned};
 use socket2::{Domain, Protocol, Type};
 
 #[cfg(any(feature = "native-tls", feature = "rustls-tls", feature = "boring-tls"))]
 use super::InnerTlsParameters;
-use super::TlsParameters;
+use super::{ConnectionState, TlsParameters};
 use crate::transport::smtp::{error, Error};
 
 /// A network stream
 pub struct NetworkStream {
     inner: InnerNetworkStream,
+    state: ConnectionState,
 }
 
 /// Represents the different types of underlying network streams
@@ -40,53 +40,49 @@ enum InnerNetworkStream {
     RustlsTls(StreamOwned<ClientConnection, TcpStream>),
     #[cfg(feature = "boring-tls")]
     BoringTls(SslStream<TcpStream>),
-    /// Can't be built
-    None,
 }
 
 impl NetworkStream {
     fn new(inner: InnerNetworkStream) -> Self {
-        if let InnerNetworkStream::None = inner {
+        NetworkStream {
-            debug_assert!(false, "InnerNetworkStream::None must never be built");
+            inner,
+            state: ConnectionState::Ok,
+        }
     }
 
-        NetworkStream { inner }
+    pub(super) fn state(&self) -> ConnectionState {
+        self.state
+    }
+
+    pub(super) fn set_state(&mut self, state: ConnectionState) {
+        self.state = state;
     }
 
     /// 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")]
-            InnerNetworkStream::RustlsTls(ref s) => s.get_ref().peer_addr(),
+            InnerNetworkStream::RustlsTls(s) => s.get_ref().peer_addr(),
             #[cfg(feature = "boring-tls")]
-            InnerNetworkStream::BoringTls(ref s) => s.get_ref().peer_addr(),
+            InnerNetworkStream::BoringTls(s) => s.get_ref().peer_addr(),
-            InnerNetworkStream::None => {
-                debug_assert!(false, "InnerNetworkStream::None must never be built");
-                Ok(SocketAddr::V4(SocketAddrV4::new(
-                    Ipv4Addr::new(127, 0, 0, 1),
-                    80,
-                )))
-            }
         }
     }
 
     /// Shutdowns the connection
-    pub fn shutdown(&self, how: Shutdown) -> io::Result<()> {
+    pub fn shutdown(&mut self, how: Shutdown) -> io::Result<()> {
-        match self.inner {
+        self.state = ConnectionState::Closed;
-            InnerNetworkStream::Tcp(ref s) => s.shutdown(how),
+
+        match &self.inner {
+            InnerNetworkStream::Tcp(s) => s.shutdown(how),
             #[cfg(feature = "native-tls")]
-            InnerNetworkStream::NativeTls(ref s) => s.get_ref().shutdown(how),
+            InnerNetworkStream::NativeTls(s) => s.get_ref().shutdown(how),
             #[cfg(feature = "rustls-tls")]
-            InnerNetworkStream::RustlsTls(ref s) => s.get_ref().shutdown(how),
+            InnerNetworkStream::RustlsTls(s) => s.get_ref().shutdown(how),
             #[cfg(feature = "boring-tls")]
-            InnerNetworkStream::BoringTls(ref s) => s.get_ref().shutdown(how),
+            InnerNetworkStream::BoringTls(s) => s.get_ref().shutdown(how),
-            InnerNetworkStream::None => {
-                debug_assert!(false, "InnerNetworkStream::None must never be built");
-                Ok(())
-            }
         }
     }
 
@@ -139,13 +135,13 @@ impl NetworkStream {
         let tcp_stream = try_connect(server, timeout, local_addr)?;
         let mut stream = NetworkStream::new(InnerNetworkStream::Tcp(tcp_stream));
         if let Some(tls_parameters) = tls_parameters {
-            stream.upgrade_tls(tls_parameters)?;
+            stream = stream.upgrade_tls(tls_parameters)?;
         }
         Ok(stream)
     }
 
-    pub fn upgrade_tls(&mut self, tls_parameters: &TlsParameters) -> Result<(), Error> {
+    pub fn upgrade_tls(self, tls_parameters: &TlsParameters) -> Result<Self, Error> {
-        match &self.inner {
+        match self.inner {
             #[cfg(not(any(
                 feature = "native-tls",
                 feature = "rustls-tls",
@@ -157,18 +153,14 @@ impl NetworkStream {
             }
 
             #[cfg(any(feature = "native-tls", feature = "rustls-tls", feature = "boring-tls"))]
-            InnerNetworkStream::Tcp(_) => {
+            InnerNetworkStream::Tcp(tcp_stream) => {
-                // get owned TcpStream
+                let inner = Self::upgrade_tls_impl(tcp_stream, tls_parameters)?;
-                let tcp_stream = mem::replace(&mut self.inner, InnerNetworkStream::None);
+                Ok(Self {
-                let tcp_stream = match tcp_stream {
+                    inner,
-                    InnerNetworkStream::Tcp(tcp_stream) => tcp_stream,
+                    state: ConnectionState::Ok,
-                    _ => unreachable!(),
+                })
-                };
-
-                self.inner = Self::upgrade_tls_impl(tcp_stream, tls_parameters)?;
-                Ok(())
             }
-            _ => Ok(()),
+            _ => Ok(self),
         }
     }
 
@@ -189,7 +181,7 @@ impl NetworkStream {
             InnerTlsParameters::RustlsTls(connector) => {
                 let domain = ServerName::try_from(tls_parameters.domain())
                     .map_err(|_| error::connection("domain isn't a valid DNS name"))?;
-                let connection = ClientConnection::new(Arc::clone(connector), domain)
+                let connection = ClientConnection::new(Arc::clone(connector), domain.to_owned())
                     .map_err(error::connection)?;
                 let stream = StreamOwned::new(connection, tcp_stream);
                 InnerNetworkStream::RustlsTls(stream)
@@ -208,7 +200,7 @@ impl NetworkStream {
     }
 
     pub fn is_encrypted(&self) -> bool {
-        match self.inner {
+        match &self.inner {
             InnerNetworkStream::Tcp(_) => false,
             #[cfg(feature = "native-tls")]
             InnerNetworkStream::NativeTls(_) => true,
@@ -216,10 +208,6 @@ impl NetworkStream {
             InnerNetworkStream::RustlsTls(_) => true,
             #[cfg(feature = "boring-tls")]
             InnerNetworkStream::BoringTls(_) => true,
-            InnerNetworkStream::None => {
-                debug_assert!(false, "InnerNetworkStream::None must never be built");
-                false
-            }
         }
     }
 
@@ -241,8 +229,7 @@ impl NetworkStream {
                 .unwrap()
                 .first()
                 .unwrap()
-                .clone()
+                .to_vec()),
-                .0),
             #[cfg(feature = "boring-tls")]
             InnerNetworkStream::BoringTls(stream) => Ok(stream
                 .ssl()
@@ -250,111 +237,78 @@ impl NetworkStream {
                 .unwrap()
                 .to_der()
                 .map_err(error::tls)?),
-            InnerNetworkStream::None => panic!("InnerNetworkStream::None must never be built"),
         }
     }
 
     pub fn set_read_timeout(&mut self, duration: Option<Duration>) -> io::Result<()> {
-        match self.inner {
+        match &mut self.inner {
-            InnerNetworkStream::Tcp(ref mut stream) => stream.set_read_timeout(duration),
+            InnerNetworkStream::Tcp(stream) => stream.set_read_timeout(duration),
             #[cfg(feature = "native-tls")]
-            InnerNetworkStream::NativeTls(ref mut stream) => {
+            InnerNetworkStream::NativeTls(stream) => stream.get_ref().set_read_timeout(duration),
-                stream.get_ref().set_read_timeout(duration)
-            }
             #[cfg(feature = "rustls-tls")]
-            InnerNetworkStream::RustlsTls(ref mut stream) => {
+            InnerNetworkStream::RustlsTls(stream) => stream.get_ref().set_read_timeout(duration),
-                stream.get_ref().set_read_timeout(duration)
-            }
             #[cfg(feature = "boring-tls")]
-            InnerNetworkStream::BoringTls(ref mut stream) => {
+            InnerNetworkStream::BoringTls(stream) => stream.get_ref().set_read_timeout(duration),
-                stream.get_ref().set_read_timeout(duration)
-            }
-            InnerNetworkStream::None => {
-                debug_assert!(false, "InnerNetworkStream::None must never be built");
-                Ok(())
-            }
         }
     }
 
     /// 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-tls")]
-            InnerNetworkStream::RustlsTls(ref mut stream) => {
+            InnerNetworkStream::RustlsTls(stream) => stream.get_ref().set_write_timeout(duration),
-                stream.get_ref().set_write_timeout(duration)
-            }
             #[cfg(feature = "boring-tls")]
-            InnerNetworkStream::BoringTls(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(())
-            }
         }
     }
 }
 
 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")]
-            InnerNetworkStream::RustlsTls(ref mut s) => s.read(buf),
+            InnerNetworkStream::RustlsTls(s) => s.read(buf),
             #[cfg(feature = "boring-tls")]
-            InnerNetworkStream::BoringTls(ref mut s) => s.read(buf),
+            InnerNetworkStream::BoringTls(s) => s.read(buf),
-            InnerNetworkStream::None => {
-                debug_assert!(false, "InnerNetworkStream::None must never be built");
-                Ok(0)
-            }
         }
     }
 }
 
 impl Write for NetworkStream {
     fn write(&mut self, buf: &[u8]) -> io::Result<usize> {
-        match self.inner {
+        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")]
-            InnerNetworkStream::RustlsTls(ref mut s) => s.write(buf),
+            InnerNetworkStream::RustlsTls(s) => s.write(buf),
             #[cfg(feature = "boring-tls")]
-            InnerNetworkStream::BoringTls(ref mut s) => s.write(buf),
+            InnerNetworkStream::BoringTls(s) => s.write(buf),
-            InnerNetworkStream::None => {
-                debug_assert!(false, "InnerNetworkStream::None must never be built");
-                Ok(0)
-            }
         }
     }
 
     fn flush(&mut self) -> io::Result<()> {
-        match self.inner {
+        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")]
-            InnerNetworkStream::RustlsTls(ref mut s) => s.flush(),
+            InnerNetworkStream::RustlsTls(s) => s.flush(),
             #[cfg(feature = "boring-tls")]
-            InnerNetworkStream::BoringTls(ref mut s) => s.flush(),
+            InnerNetworkStream::BoringTls(s) => s.flush(),
-            InnerNetworkStream::None => {
-                debug_assert!(false, "InnerNetworkStream::None must never be built");
-                Ok(())
-            }
         }
     }
 }
 
 /// If the local address is set, binds the socket to this address.
-/// If local address is not set, then destination address is required to determine to the default
+/// 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(

src/transport/smtp/client/tls.rs

@@ -1,6 +1,6 @@
 use std::fmt::{self, Debug};
 #[cfg(feature = "rustls-tls")]
-use std::{sync::Arc, time::SystemTime};
+use std::{io, sync::Arc};
 
 #[cfg(feature = "boring-tls")]
 use boring::{
@@ -11,8 +11,10 @@ use boring::{
 use native_tls::{Protocol, TlsConnector};
 #[cfg(feature = "rustls-tls")]
 use rustls::{
-    client::{ServerCertVerified, ServerCertVerifier, WebPkiVerifier},
+    client::danger::{HandshakeSignatureValid, ServerCertVerified, ServerCertVerifier},
-    ClientConfig, Error as TlsError, RootCertStore, ServerName,
+    crypto::{verify_tls12_signature, verify_tls13_signature},
+    pki_types::{CertificateDer, ServerName, UnixTime},
+    ClientConfig, DigitallySignedStruct, Error as TlsError, RootCertStore, SignatureScheme,
 };
 
 #[cfg(any(feature = "native-tls", feature = "rustls-tls", feature = "boring-tls"))]
@@ -47,9 +49,9 @@ pub enum TlsVersion {
     Tlsv12,
     /// TLS 1.3
     ///
-    /// The most secure option, altough not supported by all SMTP servers.
+    /// The most secure option, although not supported by all SMTP servers.
     ///
-    /// Altough it is technically supported by all TLS backends,
+    /// Although it is technically supported by all TLS backends,
     /// trying to set it for `native-tls` will give a runtime error.
     Tlsv13,
 }
@@ -87,11 +89,11 @@ 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"))]
+            #[cfg(any(feature = "native-tls", feature = "rustls-tls", feature = "boring-tls"))]
             Self::Opportunistic(_) => f.pad("Opportunistic"),
-            #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+            #[cfg(any(feature = "native-tls", feature = "rustls-tls", feature = "boring-tls"))]
             Self::Required(_) => f.pad("Required"),
-            #[cfg(any(feature = "native-tls", feature = "rustls", feature = "boring-tls"))]
+            #[cfg(any(feature = "native-tls", feature = "rustls-tls", feature = "boring-tls"))]
             Self::Wrapper(_) => f.pad("Wrapper"),
         }
     }
@@ -99,7 +101,7 @@ impl Debug for Tls {
 
 /// Source for the base set of root certificates to trust.
 #[allow(missing_copy_implementations)]
-#[derive(Clone, Debug)]
+#[derive(Clone, Debug, Default)]
 pub enum CertificateStore {
     /// Use the default for the TLS backend.
     ///
@@ -110,22 +112,17 @@ pub enum CertificateStore {
     /// enabled, or will fall back to `webpki-roots`.
     ///
     /// The boring-tls backend uses the same logic as OpenSSL on all platforms.
+    #[default]
     Default,
     /// Use a hardcoded set of Mozilla roots via the `webpki-roots` crate.
     ///
     /// This option is only available in the rustls backend.
-    #[cfg(feature = "webpki-roots")]
+    #[cfg(feature = "rustls-tls")]
     WebpkiRoots,
     /// Don't use any system certificates.
     None,
 }
 
-impl Default for CertificateStore {
-    fn default() -> Self {
-        CertificateStore::Default
-    }
-}
-
 /// Parameters to use for secure clients
 #[derive(Clone)]
 pub struct TlsParameters {
@@ -342,8 +339,6 @@ impl TlsParametersBuilder {
     #[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 just_version3 = &[&rustls::version::TLS13];
         let supported_versions = match self.min_tls_version {
             TlsVersion::Tlsv10 => {
@@ -356,58 +351,38 @@ impl TlsParametersBuilder {
             TlsVersion::Tlsv13 => just_version3,
         };
 
-        let tls = tls
+        let tls = ClientConfig::builder_with_protocol_versions(supported_versions);
-            .with_safe_default_cipher_suites()
-            .with_safe_default_kx_groups()
-            .with_protocol_versions(supported_versions)
-            .map_err(error::tls)?;
 
         let tls = if self.accept_invalid_certs {
-            tls.with_custom_certificate_verifier(Arc::new(InvalidCertsVerifier {}))
+            tls.dangerous()
+                .with_custom_certificate_verifier(Arc::new(InvalidCertsVerifier {}))
         } else {
             let mut root_cert_store = RootCertStore::empty();
 
             #[cfg(feature = "rustls-native-certs")]
             fn load_native_roots(store: &mut RootCertStore) -> Result<(), Error> {
                 let native_certs = rustls_native_certs::load_native_certs().map_err(error::tls)?;
-                let mut valid_count = 0;
+                let (added, ignored) = store.add_parsable_certificates(native_certs);
-                let mut invalid_count = 0;
-                for cert in native_certs {
-                    match store.add(&rustls::Certificate(cert.0)) {
-                        Ok(_) => valid_count += 1,
-                        Err(err) => {
-                            #[cfg(feature = "tracing")]
-                            tracing::debug!("certificate parsing failed: {:?}", err);
-                            invalid_count += 1;
-                        }
-                    }
-                }
                 #[cfg(feature = "tracing")]
                 tracing::debug!(
-                    "loaded platform certs with {valid_count} valid and {invalid_count} invalid certs"
+                    "loaded platform certs with {added} valid and {ignored} ignored (invalid) certs"
                 );
                 Ok(())
             }
 
-            #[cfg(feature = "webpki-roots")]
+            #[cfg(feature = "rustls-tls")]
             fn load_webpki_roots(store: &mut RootCertStore) {
-                store.add_server_trust_anchors(webpki_roots::TLS_SERVER_ROOTS.0.iter().map(|ta| {
+                store.extend(webpki_roots::TLS_SERVER_ROOTS.iter().cloned());
-                    rustls::OwnedTrustAnchor::from_subject_spki_name_constraints(
-                        ta.subject,
-                        ta.spki,
-                        ta.name_constraints,
-                    )
-                }));
             }
 
             match self.cert_store {
                 CertificateStore::Default => {
                     #[cfg(feature = "rustls-native-certs")]
                     load_native_roots(&mut root_cert_store)?;
-                    #[cfg(all(not(feature = "rustls-native-certs"), feature = "webpki-roots"))]
+                    #[cfg(not(feature = "rustls-native-certs"))]
                     load_webpki_roots(&mut root_cert_store);
                 }
-                #[cfg(feature = "webpki-roots")]
+                #[cfg(feature = "rustls-tls")]
                 CertificateStore::WebpkiRoots => {
                     load_webpki_roots(&mut root_cert_store);
                 }
@@ -415,14 +390,11 @@ impl TlsParametersBuilder {
             }
             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(rustls_cert).map_err(error::tls)?;
                 }
             }
 
-            tls.with_custom_certificate_verifier(Arc::new(WebPkiVerifier::new(
+            tls.with_root_certificates(root_cert_store)
-                root_cert_store,
-                None,
-            )))
         };
         let tls = tls.with_no_client_auth();
 
@@ -496,7 +468,7 @@ pub struct Certificate {
     #[cfg(feature = "native-tls")]
     native_tls: native_tls::Certificate,
     #[cfg(feature = "rustls-tls")]
-    rustls: Vec<rustls::Certificate>,
+    rustls: Vec<CertificateDer<'static>>,
     #[cfg(feature = "boring-tls")]
     boring_tls: boring::x509::X509,
 }
@@ -515,7 +487,7 @@ impl Certificate {
             #[cfg(feature = "native-tls")]
             native_tls: native_tls_cert,
             #[cfg(feature = "rustls-tls")]
-            rustls: vec![rustls::Certificate(der)],
+            rustls: vec![der.into()],
             #[cfg(feature = "boring-tls")]
             boring_tls: boring_tls_cert,
         })
@@ -535,10 +507,8 @@ impl Certificate {
 
             let mut pem = Cursor::new(pem);
             rustls_pemfile::certs(&mut pem)
+                .collect::<io::Result<Vec<_>>>()
                 .map_err(|_| error::tls("invalid certificates"))?
-                .into_iter()
-                .map(rustls::Certificate)
-                .collect::<Vec<_>>()
         };
 
         Ok(Self {
@@ -559,19 +529,53 @@ impl Debug for Certificate {
 }
 
 #[cfg(feature = "rustls-tls")]
+#[derive(Debug)]
 struct InvalidCertsVerifier;
 
 #[cfg(feature = "rustls-tls")]
 impl ServerCertVerifier for InvalidCertsVerifier {
     fn verify_server_cert(
         &self,
-        _end_entity: &rustls::Certificate,
+        _end_entity: &CertificateDer<'_>,
-        _intermediates: &[rustls::Certificate],
+        _intermediates: &[CertificateDer<'_>],
-        _server_name: &ServerName,
+        _server_name: &ServerName<'_>,
-        _scts: &mut dyn Iterator<Item = &[u8]>,
         _ocsp_response: &[u8],
-        _now: SystemTime,
+        _now: UnixTime,
     ) -> Result<ServerCertVerified, TlsError> {
         Ok(ServerCertVerified::assertion())
     }
+
+    fn verify_tls12_signature(
+        &self,
+        message: &[u8],
+        cert: &CertificateDer<'_>,
+        dss: &DigitallySignedStruct,
+    ) -> Result<HandshakeSignatureValid, TlsError> {
+        verify_tls12_signature(
+            message,
+            cert,
+            dss,
+            &rustls::crypto::ring::default_provider().signature_verification_algorithms,
+        )
+    }
+
+    fn verify_tls13_signature(
+        &self,
+        message: &[u8],
+        cert: &CertificateDer<'_>,
+        dss: &DigitallySignedStruct,
+    ) -> Result<HandshakeSignatureValid, TlsError> {
+        verify_tls13_signature(
+            message,
+            cert,
+            dss,
+            &rustls::crypto::ring::default_provider().signature_verification_algorithms,
+        )
+    }
+
+    fn supported_verify_schemes(&self) -> Vec<SignatureScheme> {
+        rustls::crypto::ring::default_provider()
+            .signature_verification_algorithms
+            .supported_schemes()
+    }
 }

src/transport/smtp/connection_url.rs

@@ -0,0 +1,129 @@
+use url::Url;
+
+#[cfg(any(feature = "native-tls", feature = "rustls-tls", feature = "boring-tls"))]
+use super::client::{Tls, TlsParameters};
+#[cfg(any(feature = "tokio1", feature = "async-std1"))]
+use super::AsyncSmtpTransportBuilder;
+use super::{
+    authentication::Credentials, error, extension::ClientId, Error, SmtpTransportBuilder,
+    SMTP_PORT, SUBMISSIONS_PORT, SUBMISSION_PORT,
+};
+
+pub(crate) trait TransportBuilder {
+    fn new<T: Into<String>>(server: T) -> Self;
+    fn tls(self, tls: super::Tls) -> Self;
+    fn port(self, port: u16) -> Self;
+    fn credentials(self, credentials: Credentials) -> Self;
+    fn hello_name(self, name: ClientId) -> Self;
+}
+
+impl TransportBuilder for SmtpTransportBuilder {
+    fn new<T: Into<String>>(server: T) -> Self {
+        Self::new(server)
+    }
+
+    fn tls(self, tls: super::Tls) -> Self {
+        self.tls(tls)
+    }
+
+    fn port(self, port: u16) -> Self {
+        self.port(port)
+    }
+
+    fn credentials(self, credentials: Credentials) -> Self {
+        self.credentials(credentials)
+    }
+
+    fn hello_name(self, name: ClientId) -> Self {
+        self.hello_name(name)
+    }
+}
+
+#[cfg(any(feature = "tokio1", feature = "async-std1"))]
+impl TransportBuilder for AsyncSmtpTransportBuilder {
+    fn new<T: Into<String>>(server: T) -> Self {
+        Self::new(server)
+    }
+
+    fn tls(self, tls: super::Tls) -> Self {
+        self.tls(tls)
+    }
+
+    fn port(self, port: u16) -> Self {
+        self.port(port)
+    }
+
+    fn credentials(self, credentials: Credentials) -> Self {
+        self.credentials(credentials)
+    }
+
+    fn hello_name(self, name: ClientId) -> Self {
+        self.hello_name(name)
+    }
+}
+
+/// Create a new SmtpTransportBuilder or AsyncSmtpTransportBuilder from a connection URL
+pub(crate) fn from_connection_url<B: TransportBuilder>(connection_url: &str) -> Result<B, Error> {
+    let connection_url = Url::parse(connection_url).map_err(error::connection)?;
+    let tls: Option<String> = connection_url
+        .query_pairs()
+        .find(|(k, _)| k == "tls")
+        .map(|(_, v)| v.to_string());
+
+    let host = connection_url
+        .host_str()
+        .ok_or_else(|| error::connection("smtp host undefined"))?;
+
+    let mut builder = B::new(host);
+
+    match (connection_url.scheme(), tls.as_deref()) {
+        ("smtp", None) => {
+            builder = builder.port(connection_url.port().unwrap_or(SMTP_PORT));
+        }
+        #[cfg(any(feature = "native-tls", feature = "rustls-tls", 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-tls", 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-tls", 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| 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

@@ -119,7 +119,7 @@ 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);
         }
 
@@ -129,22 +129,22 @@ 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", feature = "boring-tls"))]
             Kind::Tls => f.write_str("tls error")?,
-            Kind::Transient(ref code) => {
+            Kind::Transient(code) => {
                 write!(f, "transient error ({code})")?;
             }
-            Kind::Permanent(ref code) => {
+            Kind::Permanent(code) => {
                 write!(f, "permanent error ({code})")?;
             }
         };
 
-        if let Some(ref e) = self.inner.source {
+        if let Some(e) = &self.inner.source {
             write!(f, ": {e}")?;
         }
 

src/transport/smtp/extension.rs

@@ -4,7 +4,6 @@ use std::{
     collections::HashSet,
     fmt::{self, Display, Formatter},
     net::{Ipv4Addr, Ipv6Addr},
-    result::Result,
 };
 
 use crate::transport::smtp::{
@@ -53,10 +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}]"),
         }
     }
 }
@@ -93,11 +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}"),
         }
     }
 }
@@ -190,7 +189,7 @@ 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) {
@@ -227,16 +226,16 @@ 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::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),
         }
@@ -277,13 +276,13 @@ 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),
         }

src/transport/smtp/mod.rs

@@ -154,6 +154,7 @@ mod async_transport;
 pub mod authentication;
 pub mod client;
 pub mod commands;
+mod connection_url;
 mod error;
 pub mod extension;
 #[cfg(feature = "pool")]

src/transport/smtp/pool/async_impl.rs

@@ -2,7 +2,7 @@ use std::{
     fmt::{self, Debug},
     mem,
     ops::{Deref, DerefMut},
-    sync::Arc,
+    sync::{Arc, OnceLock},
     time::{Duration, Instant},
 };
 
@@ -10,7 +10,6 @@ use futures_util::{
     lock::Mutex,
     stream::{self, StreamExt},
 };
-use once_cell::sync::OnceCell;
 
 use super::{
     super::{client::AsyncSmtpConnection, Error},
@@ -22,7 +21,7 @@ pub struct Pool<E: Executor> {
     config: PoolConfig,
     connections: Mutex<Vec<ParkedConnection>>,
     client: AsyncSmtpClient<E>,
-    handle: OnceCell<E::Handle>,
+    handle: OnceLock<E::Handle>,
 }
 
 struct ParkedConnection {
@@ -41,7 +40,7 @@ impl<E: Executor> Pool<E> {
             config,
             connections: Mutex::new(Vec::new()),
             client,
-            handle: OnceCell::new(),
+            handle: OnceLock::new(),
         });
 
         {

src/transport/smtp/response.rs

@@ -5,7 +5,6 @@ use std::{
     fmt::{Display, Formatter, Result},
     result,
     str::FromStr,
-    string::ToString,
 };
 
 use nom::{
@@ -19,7 +18,7 @@ use nom::{
 
 use crate::transport::smtp::{error, Error};
 
-/// First digit indicates severity
+/// The first digit indicates severity
 #[derive(PartialEq, Eq, Copy, Clone, Debug)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 pub enum Severity {
@@ -132,6 +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
@@ -317,6 +322,17 @@ 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";

src/transport/smtp/transport.rs

@@ -1,6 +1,6 @@
 #[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;
@@ -38,6 +38,14 @@ impl Transport for SmtpTransport {
     }
 }
 
+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 {
     /// Simple and secure transport, using TLS connections to communicate with the SMTP server
     ///
@@ -58,7 +66,7 @@ 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.
@@ -95,29 +103,106 @@ 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 and port can be provided in a single URL.
+    /// Use the scheme `smtp` for an unencrypted relay (optionally in combination with the
+    /// `tls` parameter to allow/require STARTTLS) or `smtps` for SMTP over TLS.
+    /// The path section of the url can be used to set an alternative name for
+    /// the HELO / EHLO command.
+    /// For example `smtps://username:password@smtp.example.com/client.example.com:465`
+    /// will set the HELO / EHLO name `client.example.com`.
+    ///
+    /// <table>
+    ///   <thead>
+    ///     <tr>
+    ///       <th>scheme</th>
+    ///       <th>tls parameter</th>
+    ///       <th>example</th>
+    ///       <th>remarks</th>
+    ///     </tr>
+    ///   </thead>
+    ///   <tbody>
+    ///     <tr>
+    ///      <td>smtps</td>
+    ///      <td>-</td>
+    ///      <td>smtps://smtp.example.com</td>
+    ///      <td>SMTP over TLS, recommended method</td>
+    ///     </tr>
+    ///     <tr>
+    ///      <td>smtp</td>
+    ///      <td>required</td>
+    ///      <td>smtp://smtp.example.com?tls=required</td>
+    ///      <td>SMTP with STARTTLS required, when SMTP over TLS is not available</td>
+    ///     </tr>
+    ///     <tr>
+    ///      <td>smtp</td>
+    ///      <td>opportunistic</td>
+    ///      <td>smtp://smtp.example.com?tls=opportunistic</td>
+    ///      <td>
+    ///         SMTP with optionally STARTTLS when supported by the server.
+    ///         Caution: this method is vulnerable to a man-in-the-middle attack.
+    ///         Not recommended for production use.
+    ///       </td>
+    ///     </tr>
+    ///     <tr>
+    ///      <td>smtp</td>
+    ///      <td>-</td>
+    ///      <td>smtp://smtp.example.com</td>
+    ///      <td>Unencrypted SMTP, not recommended for production use.</td>
+    ///     </tr>
+    ///   </tbody>
+    /// </table>
+    ///
+    /// ```rust,no_run
+    /// use lettre::{
+    ///     message::header::ContentType, transport::smtp::authentication::Credentials, Message,
+    ///     SmtpTransport, Transport,
+    /// };
+    ///
+    /// let email = Message::builder()
+    ///     .from("NoBody <nobody@domain.tld>".parse().unwrap())
+    ///     .reply_to("Yuin <yuin@domain.tld>".parse().unwrap())
+    ///     .to("Hei <hei@domain.tld>".parse().unwrap())
+    ///     .subject("Happy new year")
+    ///     .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:465")
+    ///     .unwrap()
+    ///     .build();
+    ///
+    /// // Send the email
+    /// match mailer.send(&email) {
+    ///     Ok(_) => println!("Email sent successfully!"),
+    ///     Err(e) => panic!("Could not send email: {e:?}"),
+    /// }
+    /// ```
+    #[cfg(any(feature = "native-tls", feature = "rustls-tls", feature = "boring-tls"))]
+    #[cfg_attr(
+        docsrs,
+        doc(cfg(any(feature = "native-tls", feature = "rustls-tls", 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()?;
 
@@ -141,6 +226,20 @@ 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;
@@ -194,7 +293,7 @@ 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 };
@@ -218,9 +317,9 @@ impl SmtpClient {
     /// Handles encryption and authentication
     pub 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", feature = "boring-tls"))]
-            Tls::Wrapper(ref tls_parameters) => Some(tls_parameters),
+            Tls::Wrapper(tls_parameters) => Some(tls_parameters),
             _ => None,
         };
 
@@ -234,14 +333,14 @@ impl SmtpClient {
         )?;
 
         #[cfg(any(feature = "native-tls", feature = "rustls-tls", 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)?;
+                    conn = 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)?;
+                conn = conn.starttls(tls_parameters, &self.info.hello_name)?;
             }
             _ => (),
         }
@@ -252,3 +351,78 @@ 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(_)));
+    }
+}