Add documentation to undocumented items (#793)

Instead of injecting spaces to ensure that lines stay under 76 characters only wrap at whitespace characters. This avoids changing the headers.

A best-effort to keep lines under 76 characters is still done, however it is only done at whitespace. Notably there is no hard wrap enforced. This means that it is possible for headers to break the 1000 character line-length limit in the specification. It is just hoped that the receiver will allow long lines in this case.

Closes #688

Co-authored-by: Kevin Cox <kevincox@kevincox.ca>

.editorconfig

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

.github/workflows/test.yml

@@ -124,6 +124,9 @@ jobs:
       - name: Install dkimverify
         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
+
       - name: Test with no default features
         run: cargo test --no-default-features
 

CHANGELOG.md

@@ -29,6 +29,7 @@ Several breaking changes were made between 0.9 and 0.10, but changes should be s
 * Refactor `TlsParameters` implementation to not expose the internal TLS library
 * `FileTransport` writes emails into `.eml` instead of `.json`
 * When the hostname feature is disabled or hostname cannot be fetched, `127.0.0.1` is used instead of `localhost` as EHLO parameter (for better RFC compliance and mail server compatibility)
+* The `sendmail` and `file` transports aren't enabled by default anymore.
 * The `new` method of `ClientId` is deprecated
 * Rename `serde-impls` feature to `serde`
 * The `SendmailTransport` now uses the `sendmail` command in current `PATH` by default instead of

Cargo.toml

@@ -1,7 +1,7 @@
 [package]
 name = "lettre"
 # remember to update html_root_url and README.md (Cargo.toml example and deps.rs badge)
-version = "0.10.0-rc.5"
+version = "0.10.0"
 description = "Email client"
 readme = "README.md"
 homepage = "https://lettre.rs"
@@ -20,7 +20,7 @@ maintenance = { status = "actively-developed" }
 
 [dependencies]
 idna = "0.2"
-once_cell = "1"
+once_cell = { version = "1", optional = true }
 tracing = { version = "0.1.16", default-features = false, features = ["std"], optional = true } # feature
 
 # builder
@@ -29,22 +29,22 @@ mime = { version = "0.3.4", optional = true }
 fastrand = { version = "1.4", optional = true }
 quoted_printable = { version = "0.4", optional = true }
 base64 = { version = "0.13", optional = true }
-regex = { version = "1", default-features = false, features = ["std", "unicode-case"] }
-email-encoding = { version = "0.1", optional = true }
+email-encoding = { version = "0.1.1", optional = true }
 
 # file transport
-uuid = { version = "0.8", features = ["v4"], optional = true }
+uuid = { version = "1", features = ["v4"], optional = true }
 serde = { version = "1", optional = true, features = ["derive"] }
 serde_json = { version = "1", optional = true }
 
-# smtp
+# smtp-transport
 nom = { version = "7", optional = true }
 hostname = { version = "0.3", optional = true } # feature
+socket2 = { version = "0.4.4", optional = true }
 
 ## tls
 native-tls = { version = "0.2", optional = true } # feature
 rustls = { version = "0.20", features = ["dangerous_configuration"], optional = true }
-rustls-pemfile = { version = "0.3", optional = true }
+rustls-pemfile = { version = "1", optional = true }
 webpki-roots = { version = "0.22", optional = true }
 
 # async
@@ -64,18 +64,24 @@ tokio1_rustls = { package = "tokio-rustls", version = "0.23", optional = true }
 
 ## dkim
 sha2 = { version = "0.10", optional = true }
-rsa = { version = "0.6.0-pre", optional = true }
+rsa = { version = "0.6.0", optional = true }
 ed25519-dalek = { version = "1.0.1", optional = true }
+regex = { version = "1", default-features = false, features = ["std"], optional = true }
+
+# email formats
+email_address = { version = "0.2.1", default-features = false }
 
 [dev-dependencies]
+pretty_assertions = "1"
 criterion = "0.3"
+tracing = { version = "0.1.16", default-features = false, features = ["std"] }
 tracing-subscriber = "0.3"
 glob = "0.3"
 walkdir = "2"
 tokio1_crate = { package = "tokio", version = "1", features = ["macros", "rt-multi-thread"] }
 async-std = { version = "1.8", features = ["attributes"] }
 serde_json = "1"
-maud = "0.22.1"
+maud = "0.23"
 
 [[bench]]
 harness = false
@@ -83,14 +89,14 @@ name = "transport_smtp"
 
 [features]
 default = ["smtp-transport", "pool", "native-tls", "hostname", "builder"]
-builder = ["httpdate", "mime", "base64", "fastrand", "quoted_printable", "email-encoding"]
+builder = ["httpdate", "mime", "fastrand", "quoted_printable", "email-encoding"]
 mime03 = ["mime"]
 
 # transports
 file-transport = ["uuid"]
 file-transport-envelope = ["serde", "serde_json", "file-transport"]
 sendmail-transport = []
-smtp-transport = ["base64", "nom"]
+smtp-transport = ["base64", "nom", "socket2", "once_cell"]
 
 pool = ["futures-util"]
 
@@ -104,12 +110,16 @@ tokio1 = ["tokio1_crate", "async-trait", "futures-io", "futures-util"]
 tokio1-native-tls = ["tokio1", "native-tls", "tokio1_native_tls_crate"]
 tokio1-rustls-tls = ["tokio1", "rustls-tls", "tokio1_rustls"]
 
-dkim = ["sha2", "rsa", "ed25519-dalek"]
+dkim = ["base64", "sha2", "rsa", "ed25519-dalek", "regex", "once_cell"]
 
 [package.metadata.docs.rs]
 all-features = true
 rustdoc-args = ["--cfg", "docsrs", "--cfg", "lettre_ignore_tls_mismatch"]
 
+[[example]]
+name = "autoconfigure"
+required-features = ["smtp-transport", "native-tls"]
+
 [[example]]
 name = "basic_html"
 required-features = ["file-transport", "builder"]

README.md

@@ -28,27 +28,14 @@
 </div>
 
 <div align="center">
-  <a href="https://deps.rs/crate/lettre/0.10.0-rc.5">
-    <img src="https://deps.rs/crate/lettre/0.10.0-rc.5/status.svg"
+  <a href="https://deps.rs/crate/lettre/0.10.0">
+    <img src="https://deps.rs/crate/lettre/0.10.0/status.svg"
       alt="dependency status" />
   </a>
 </div>
 
 ---
 
-**NOTE**: this readme refers to the 0.10 version of lettre, which is
-in release candidate state. Use the [`v0.9.x`](https://github.com/lettre/lettre/tree/v0.9.x)
-branch for the previous stable release.
-
-0.10 is already widely used and is already thought to be more reliable than 0.9, so it should generally be used
-for new projects.
-
-We'd love to hear your feedback about 0.10 design and APIs before final release!
-Start a [discussion](https://github.com/lettre/lettre/discussions) in the repository, whether for
-feedback or if you need help or advice using or upgrading lettre 0.10.
-
----
-
 ## Features
 
 Lettre provides the following features:
@@ -63,15 +50,20 @@ Lettre does not provide (for now):
 
 * Email parsing
 
+## Supported Rust Versions
+
+Lettre supports all Rust versions released in the last 6 months. At the time of writing
+the minimum supported Rust version is 1.56, 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 1.56.0 or newer.
 To use this library, add the following to your `Cargo.toml`:
 
-
 ```toml
 [dependencies]
-lettre = "0.10.0-rc.5"
+lettre = "0.10"
 ```
 
 ```rust,no_run
@@ -101,10 +93,18 @@ match mailer.send(&email) {
 }
 ```
 
+## Not sure of which connect options to use?
+
+Clone the lettre git repository and run the following command (replacing `SMTP_HOST` with your SMTP server's hostname)
+
+```shell
+cargo run --example autoconfigure SMTP_HOST
+```
+
 ## Testing
 
 The `lettre` tests require an open mail server listening locally on port 2525 and the `sendmail` command. If you have python installed 
-such a server can be launched with `python -m smtpd -n -c DebuggingServer localhost:2525`
+such a server can be launched with `python -m smtpd -n -c DebuggingServer 127.0.0.1:2525`
 
 Alternatively only unit tests can be run by doing `cargo test --lib`.
 

examples/autoconfigure.rs

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

src/address/types.rs

@@ -8,9 +8,8 @@ use std::{
     str::FromStr,
 };
 
+use email_address::EmailAddress;
 use idna::domain_to_ascii;
-use once_cell::sync::Lazy;
-use regex::Regex;
 
 /// Represents an email address with a user and a domain name.
 ///
@@ -55,20 +54,6 @@ pub struct Address {
     at_start: usize,
 }
 
-// Regex from the specs
-// https://html.spec.whatwg.org/multipage/forms.html#valid-e-mail-address
-// It will mark esoteric email addresses like quoted string as invalid
-static USER_RE: Lazy<Regex> =
-    Lazy::new(|| Regex::new(r"^(?i)[a-z0-9.!#$%&'*+/=?^_`{|}~-]+\z").unwrap());
-static DOMAIN_RE: Lazy<Regex> = Lazy::new(|| {
-    Regex::new(
-        r"(?i)^[a-z0-9](?:[a-z0-9-]{0,61}[a-z0-9])?(?:.[a-z0-9](?:[a-z0-9-]{0,61}[a-z0-9])?)*$",
-    )
-    .unwrap()
-});
-// literal form, ipv4 or ipv6 address (SMTP 4.1.3)
-static LITERAL_RE: Lazy<Regex> = Lazy::new(|| Regex::new(r"(?i)\[([A-f0-9:\.]+)\]\z").unwrap());
-
 impl Address {
     /// Creates a new email address from a user and domain.
     ///
@@ -126,7 +111,7 @@ impl Address {
     }
 
     pub(super) fn check_user(user: &str) -> Result<(), AddressError> {
-        if USER_RE.is_match(user) {
+        if EmailAddress::is_valid_local_part(user) {
             Ok(())
         } else {
             Err(AddressError::InvalidUser)
@@ -142,16 +127,19 @@ impl Address {
     }
 
     fn check_domain_ascii(domain: &str) -> Result<(), AddressError> {
-        if DOMAIN_RE.is_match(domain) {
+        // Domain
+        if EmailAddress::is_valid_domain(domain) {
             return Ok(());
         }
 
-        if let Some(caps) = LITERAL_RE.captures(domain) {
-            if let Some(cap) = caps.get(1) {
-                if cap.as_str().parse::<IpAddr>().is_ok() {
-                    return Ok(());
-                }
-            }
+        // IP
+        let ip = domain
+            .strip_prefix('[')
+            .and_then(|ip| ip.strip_suffix(']'))
+            .unwrap_or(domain);
+
+        if ip.parse::<IpAddr>().is_ok() {
+            return Ok(());
         }
 
         Err(AddressError::InvalidDomain)
@@ -238,7 +226,7 @@ fn check_address(val: &str) -> Result<usize, AddressError> {
     Ok(user.len())
 }
 
-#[derive(Debug, PartialEq, Clone, Copy)]
+#[derive(Debug, PartialEq, Eq, Clone, Copy)]
 /// Errors in email addresses parsing
 pub enum AddressError {
     /// Missing domain or user
@@ -269,7 +257,7 @@ mod tests {
     use super::*;
 
     #[test]
-    fn parse_address() {
+    fn ascii_address() {
         let addr_str = "something@example.com";
         let addr = Address::from_str(addr_str).unwrap();
         let addr2 = Address::new("something", "example.com").unwrap();
@@ -279,4 +267,36 @@ mod tests {
         assert_eq!(addr2.user(), "something");
         assert_eq!(addr2.domain(), "example.com");
     }
+
+    #[test]
+    fn ascii_address_ipv4() {
+        let addr_str = "something@1.1.1.1";
+        let addr = Address::from_str(addr_str).unwrap();
+        let addr2 = Address::new("something", "1.1.1.1").unwrap();
+        assert_eq!(addr, addr2);
+        assert_eq!(addr.user(), "something");
+        assert_eq!(addr.domain(), "1.1.1.1");
+        assert_eq!(addr2.user(), "something");
+        assert_eq!(addr2.domain(), "1.1.1.1");
+    }
+
+    #[test]
+    fn ascii_address_ipv6() {
+        let addr_str = "something@[2606:4700:4700::1111]";
+        let addr = Address::from_str(addr_str).unwrap();
+        let addr2 = Address::new("something", "[2606:4700:4700::1111]").unwrap();
+        assert_eq!(addr, addr2);
+        assert_eq!(addr.user(), "something");
+        assert_eq!(addr.domain(), "[2606:4700:4700::1111]");
+        assert_eq!(addr2.user(), "something");
+        assert_eq!(addr2.domain(), "[2606:4700:4700::1111]");
+    }
+
+    #[test]
+    fn check_parts() {
+        assert!(Address::check_user("aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa").is_err());
+        assert!(
+            Address::check_domain("aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa.com").is_err()
+        );
+    }
 }

src/executor.rs

@@ -109,7 +109,6 @@ impl Executor for Tokio1Executor {
     #[cfg(feature = "smtp-transport")]
     type Sleep = tokio1_crate::time::Sleep;
 
-    #[doc(hidden)]
     #[cfg(feature = "smtp-transport")]
     fn spawn<F>(fut: F) -> Self::Handle
     where
@@ -119,13 +118,11 @@ impl Executor for Tokio1Executor {
         tokio1_crate::spawn(fut)
     }
 
-    #[doc(hidden)]
     #[cfg(feature = "smtp-transport")]
     fn sleep(duration: Duration) -> Self::Sleep {
         tokio1_crate::time::sleep(duration)
     }
 
-    #[doc(hidden)]
     #[cfg(feature = "smtp-transport")]
     async fn connect(
         hostname: &str,
@@ -146,6 +143,7 @@ impl Executor for Tokio1Executor {
             timeout,
             hello_name,
             tls_parameters,
+            None,
         )
         .await?;
 
@@ -165,13 +163,11 @@ impl Executor for Tokio1Executor {
         Ok(conn)
     }
 
-    #[doc(hidden)]
     #[cfg(feature = "file-transport-envelope")]
     async fn fs_read(path: &Path) -> IoResult<Vec<u8>> {
         tokio1_crate::fs::read(path).await
     }
 
-    #[doc(hidden)]
     #[cfg(feature = "file-transport")]
     async fn fs_write(path: &Path, contents: &[u8]) -> IoResult<()> {
         tokio1_crate::fs::write(path, contents).await
@@ -209,7 +205,6 @@ impl Executor for AsyncStd1Executor {
     #[cfg(feature = "smtp-transport")]
     type Sleep = BoxFuture<'static, ()>;
 
-    #[doc(hidden)]
     #[cfg(feature = "smtp-transport")]
     fn spawn<F>(fut: F) -> Self::Handle
     where
@@ -219,14 +214,12 @@ impl Executor for AsyncStd1Executor {
         async_std::task::spawn(fut)
     }
 
-    #[doc(hidden)]
     #[cfg(feature = "smtp-transport")]
     fn sleep(duration: Duration) -> Self::Sleep {
         let fut = async move { async_std::task::sleep(duration).await };
         Box::pin(fut)
     }
 
-    #[doc(hidden)]
     #[cfg(feature = "smtp-transport")]
     async fn connect(
         hostname: &str,
@@ -266,13 +259,11 @@ impl Executor for AsyncStd1Executor {
         Ok(conn)
     }
 
-    #[doc(hidden)]
     #[cfg(feature = "file-transport-envelope")]
     async fn fs_read(path: &Path) -> IoResult<Vec<u8>> {
         async_std::fs::read(path).await
     }
 
-    #[doc(hidden)]
     #[cfg(feature = "file-transport")]
     async fn fs_write(path: &Path, contents: &[u8]) -> IoResult<()> {
         async_std::fs::write(path, contents).await
@@ -288,15 +279,13 @@ impl SpawnHandle for async_std::task::JoinHandle<()> {
 }
 
 mod private {
-    use super::*;
-
     pub trait Sealed {}
 
     #[cfg(feature = "tokio1")]
-    impl Sealed for Tokio1Executor {}
+    impl Sealed for super::Tokio1Executor {}
 
     #[cfg(feature = "async-std1")]
-    impl Sealed for AsyncStd1Executor {}
+    impl Sealed for super::AsyncStd1Executor {}
 
     #[cfg(all(feature = "smtp-transport", feature = "tokio1"))]
     impl Sealed for tokio1_crate::task::JoinHandle<()> {}

src/lib.rs

@@ -100,7 +100,7 @@
 //! [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/0.10.0-rc.5")]
+#![doc(html_root_url = "https://docs.rs/crate/lettre/0.10.0")]
 #![doc(html_favicon_url = "https://lettre.rs/favicon.ico")]
 #![doc(html_logo_url = "https://avatars0.githubusercontent.com/u/15113230?v=4")]
 #![forbid(unsafe_code)]
@@ -112,7 +112,21 @@
     unused_import_braces,
     rust_2018_idioms,
     clippy::string_add,
-    clippy::string_add_assign
+    clippy::string_add_assign,
+    clippy::clone_on_ref_ptr,
+    clippy::verbose_file_reads,
+    clippy::unnecessary_self_imports,
+    clippy::string_to_string,
+    clippy::mem_forget,
+    clippy::cast_lossless,
+    clippy::inefficient_to_string,
+    clippy::inline_always,
+    clippy::linkedlist,
+    clippy::macro_use_imports,
+    clippy::manual_assert,
+    clippy::unnecessary_join,
+    clippy::wildcard_imports,
+    clippy::zero_sized_map_values
 )]
 #![cfg_attr(docsrs, feature(doc_cfg))]
 
@@ -124,8 +138,8 @@ mod compiletime_checks {
         not(feature = "tokio1-native-tls")
     ))]
     compile_error!("Lettre is being built with the `tokio1` and the `native-tls` features, but the `tokio1-native-tls` feature hasn't been turned on.
-If you'd like to use rustls make sure that the `native-tls` hasn't been enabled by mistake (you may need to import lettre without default features)
-If you're building a library which depends on lettre import it without default features and enable just the features you need.");
+    If you were trying to opt into `rustls-tls` and did not activate `native-tls`, disable the default-features of lettre in `Cargo.toml` and manually add the required features.
+    Make sure to apply the same to any of your crate dependencies that use the `lettre` crate.");
 
     #[cfg(all(
         feature = "tokio1",
@@ -133,8 +147,8 @@ If you're building a library which depends on lettre import it without default f
         not(feature = "tokio1-rustls-tls")
     ))]
     compile_error!("Lettre is being built with the `tokio1` and the `rustls-tls` features, but the `tokio1-rustls-tls` feature hasn't been turned on.
-If you'd like to use native-tls make sure that the `rustls-tls` hasn't been enabled by mistake.
-If you're building a library which depends on lettre import it without default features and enable just the features you need.");
+    If you'd like to use `native-tls` make sure that the `rustls-tls` feature hasn't been enabled by mistake.
+    Make sure to apply the same to any of your crate dependencies that use the `lettre` crate.");
 
     /*
     #[cfg(all(
@@ -153,8 +167,8 @@ If you're building a library which depends on lettre import it without default f
     ))]
     compile_error!("Lettre is being built with the `async-std1` and the `native-tls` features, but the async-std integration doesn't support native-tls yet.
 If you'd like to work on the issue please take a look at https://github.com/lettre/lettre/issues/576.
-If you'd like to use rustls make sure that the `native-tls` hasn't been enabled by mistake (you may need to import lettre without default features)
-If you're building a library which depends on lettre import lettre without default features and enable just the features you need.");
+If you were trying to opt into `rustls-tls` and did not activate `native-tls`, disable the default-features of lettre in `Cargo.toml` and manually add the required features.
+Make sure to apply the same to any of your crate dependencies that use the `lettre` crate.");
 
     #[cfg(all(
         feature = "async-std1",
@@ -162,8 +176,8 @@ If you're building a library which depends on lettre import lettre without defau
         not(feature = "async-std1-rustls-tls")
     ))]
     compile_error!("Lettre is being built with the `async-std1` and the `rustls-tls` features, but the `async-std1-rustls-tls` feature hasn't been turned on.
-If you'd like to use native-tls make sure that the `rustls-tls` hasn't been enabled by mistake (you may need to import lettre without default features)
-If you're building a library which depends on lettre import it without default features and enable just the features you need.");
+If you'd like to use `native-tls` make sure that the `rustls-tls` hasn't been enabled by mistake.
+Make sure to apply the same to any of your crate dependencies that use the `lettre` crate.");
 }
 
 pub mod address;

src/message/body.rs

@@ -1,8 +1,4 @@
-use std::{
-    io::{self, Write},
-    mem,
-    ops::Deref,
-};
+use std::{mem, ops::Deref};
 
 use crate::message::header::ContentTransferEncoding;
 
@@ -41,7 +37,7 @@ impl Body {
     pub fn new<B: Into<MaybeString>>(buf: B) -> Self {
         let mut buf: MaybeString = buf.into();
 
-        let encoding = buf.encoding();
+        let encoding = buf.encoding(false);
         buf.encode_crlf();
         Self::new_impl(buf.into(), encoding)
     }
@@ -61,7 +57,22 @@ impl Body {
     ) -> Result<Self, Vec<u8>> {
         let mut buf: MaybeString = buf.into();
 
-        if !buf.is_encoding_ok(encoding) {
+        let best_encoding = buf.encoding(true);
+        let ok = match (encoding, best_encoding) {
+            (ContentTransferEncoding::SevenBit, ContentTransferEncoding::SevenBit) => true,
+            (
+                ContentTransferEncoding::EightBit,
+                ContentTransferEncoding::SevenBit | ContentTransferEncoding::EightBit,
+            ) => true,
+            (ContentTransferEncoding::SevenBit | ContentTransferEncoding::EightBit, _) => false,
+            (
+                ContentTransferEncoding::QuotedPrintable
+                | ContentTransferEncoding::Base64
+                | ContentTransferEncoding::Binary,
+                _,
+            ) => true,
+        };
+        if !ok {
             return Err(buf.into());
         }
 
@@ -91,36 +102,13 @@ impl Body {
                 Self::dangerous_pre_encoded(encoded, ContentTransferEncoding::QuotedPrintable)
             }
             ContentTransferEncoding::Base64 => {
-                let base64_len = buf.len() * 4 / 3 + 4;
-                let base64_endings_len = base64_len + base64_len / LINE_MAX_LENGTH;
+                let len = email_encoding::body::base64::encoded_len(buf.len());
 
-                let mut out = Vec::with_capacity(base64_endings_len);
-                {
-                    let writer = LineWrappingWriter::new(&mut out, LINE_MAX_LENGTH);
-                    let mut writer = base64::write::EncoderWriter::new(writer, base64::STANDARD);
+                let mut out = String::with_capacity(len);
+                email_encoding::body::base64::encode(&buf, &mut out)
+                    .expect("encode body as base64");
 
-                    // TODO: use writer.write_all(self.as_ref()).expect("base64 encoding never fails");
-
-                    // modified Write::write_all to work around base64 crate bug
-                    // TODO: remove once https://github.com/marshallpierce/rust-base64/issues/148 is fixed
-                    {
-                        let mut buf: &[u8] = buf.as_ref();
-                        while !buf.is_empty() {
-                            match writer.write(buf) {
-                                Ok(0) => {
-                                    // ignore 0 writes
-                                }
-                                Ok(n) => {
-                                    buf = &buf[n..];
-                                }
-                                Err(ref e) if e.kind() == std::io::ErrorKind::Interrupted => {}
-                                Err(e) => panic!("base64 encoding never fails: {}", e),
-                            }
-                        }
-                    }
-                }
-
-                Self::dangerous_pre_encoded(out, ContentTransferEncoding::Base64)
+                Self::dangerous_pre_encoded(out.into_bytes(), ContentTransferEncoding::Base64)
             }
         }
     }
@@ -153,21 +141,20 @@ impl Body {
 impl MaybeString {
     /// Suggests the best `Content-Transfer-Encoding` to be used for this `MaybeString`
     ///
-    /// If the `MaybeString` was created from a `String` composed only of US-ASCII
-    /// characters, with no lines longer than 1000 characters, then 7bit
-    /// encoding will be used, else quoted-printable will be chosen.
-    ///
-    /// If the `MaybeString` was instead created from a `Vec<u8>`, base64 encoding is always
-    /// chosen.
-    ///
-    /// `8bit` and `binary` encodings are never returned, as they may not be
-    /// supported by all SMTP servers.
-    pub fn encoding(&self) -> ContentTransferEncoding {
-        match &self {
-            Self::String(s) if is_7bit_encoded(s.as_ref()) => ContentTransferEncoding::SevenBit,
-            // TODO: consider when base64 would be a better option because of output size
-            Self::String(_) => ContentTransferEncoding::QuotedPrintable,
-            Self::Binary(_) => ContentTransferEncoding::Base64,
+    /// The `binary` encoding is never returned
+    fn encoding(&self, supports_utf8: bool) -> ContentTransferEncoding {
+        use email_encoding::body::Encoding;
+
+        let output = match self {
+            Self::String(s) => Encoding::choose(s.as_str(), supports_utf8),
+            Self::Binary(b) => Encoding::choose(b.as_slice(), supports_utf8),
+        };
+
+        match output {
+            Encoding::SevenBit => ContentTransferEncoding::SevenBit,
+            Encoding::EightBit => ContentTransferEncoding::EightBit,
+            Encoding::QuotedPrintable => ContentTransferEncoding::QuotedPrintable,
+            Encoding::Base64 => ContentTransferEncoding::Base64,
         }
     }
 
@@ -178,18 +165,6 @@ impl MaybeString {
             Self::Binary(_) => {}
         }
     }
-
-    /// Returns `true` if using `encoding` to encode this `MaybeString`
-    /// would result into an invalid encoded body.
-    fn is_encoding_ok(&self, encoding: ContentTransferEncoding) -> bool {
-        match encoding {
-            ContentTransferEncoding::SevenBit => is_7bit_encoded(self),
-            ContentTransferEncoding::EightBit => is_8bit_encoded(self),
-            ContentTransferEncoding::Binary
-            | ContentTransferEncoding::QuotedPrintable
-            | ContentTransferEncoding::Base64 => true,
-        }
-    }
 }
 
 /// A trait for something that takes an encoded [`Body`].
@@ -273,73 +248,6 @@ impl Deref for MaybeString {
     }
 }
 
-/// Checks whether it contains only US-ASCII characters,
-/// and no lines are longer than 1000 characters including the `\n` character.
-///
-/// Most efficient content encoding available
-fn is_7bit_encoded(buf: &[u8]) -> bool {
-    buf.is_ascii() && !contains_too_long_lines(buf)
-}
-
-/// Checks that no lines are longer than 1000 characters,
-/// including the `\n` character.
-/// NOTE: 8bit isn't supported by all SMTP servers.
-fn is_8bit_encoded(buf: &[u8]) -> bool {
-    !contains_too_long_lines(buf)
-}
-
-/// Checks if there are lines that are longer than 1000 characters,
-/// including the `\n` character.
-fn contains_too_long_lines(buf: &[u8]) -> bool {
-    buf.len() > 1000 && buf.split(|&b| b == b'\n').any(|line| line.len() > 999)
-}
-
-const LINE_SEPARATOR: &[u8] = b"\r\n";
-const LINE_MAX_LENGTH: usize = 78 - LINE_SEPARATOR.len();
-
-/// A `Write`r that inserts a line separator `\r\n` every `max_line_length` bytes.
-struct LineWrappingWriter<'a, W> {
-    writer: &'a mut W,
-    current_line_length: usize,
-    max_line_length: usize,
-}
-
-impl<'a, W> LineWrappingWriter<'a, W> {
-    pub fn new(writer: &'a mut W, max_line_length: usize) -> Self {
-        Self {
-            writer,
-            current_line_length: 0,
-            max_line_length,
-        }
-    }
-}
-
-impl<'a, W> Write for LineWrappingWriter<'a, W>
-where
-    W: Write,
-{
-    fn write(&mut self, buf: &[u8]) -> io::Result<usize> {
-        let remaining_line_len = self.max_line_length - self.current_line_length;
-        let write_len = std::cmp::min(buf.len(), remaining_line_len);
-
-        self.writer.write_all(&buf[..write_len])?;
-
-        if remaining_line_len == write_len {
-            self.writer.write_all(LINE_SEPARATOR)?;
-
-            self.current_line_length = 0;
-        } else {
-            self.current_line_length += write_len;
-        }
-
-        Ok(write_len)
-    }
-
-    fn flush(&mut self) -> io::Result<()> {
-        self.writer.flush()
-    }
-}
-
 /// In place conversion to CRLF line endings
 fn in_place_crlf_line_endings(string: &mut String) {
     let indices = find_all_lf_char_indices(string);
@@ -377,6 +285,8 @@ fn find_all_lf_char_indices(s: &str) -> Vec<usize> {
 
 #[cfg(test)]
 mod test {
+    use pretty_assertions::assert_eq;
+
     use super::{in_place_crlf_line_endings, Body, ContentTransferEncoding};
 
     #[test]
@@ -509,13 +419,10 @@ mod test {
 
     #[test]
     fn quoted_printable_detect() {
-        let encoded = Body::new(String::from("Привет, мир!"));
+        let encoded = Body::new(String::from("Questo messaggio è corto"));
 
         assert_eq!(encoded.encoding(), ContentTransferEncoding::QuotedPrintable);
-        assert_eq!(
-            encoded.as_ref(),
-            b"=D0=9F=D1=80=D0=B8=D0=B2=D0=B5=D1=82, =D0=BC=D0=B8=D1=80!".as_ref()
-        );
+        assert_eq!(encoded.as_ref(), b"Questo messaggio =C3=A8 corto");
     }
 
     #[test]
@@ -547,14 +454,17 @@ mod test {
 
     #[test]
     fn quoted_printable_encode_line_wrap() {
-        let encoded = Body::new(String::from("Текст письма в уникоде"));
+        let encoded = Body::new(String::from(
+            "Se lo standard 📬 fosse stato più semplice avremmo finito molto prima.",
+        ));
 
         assert_eq!(encoded.encoding(), ContentTransferEncoding::QuotedPrintable);
+        println!("{}", std::str::from_utf8(encoded.as_ref()).unwrap());
         assert_eq!(
             encoded.as_ref(),
             concat!(
-                "=D0=A2=D0=B5=D0=BA=D1=81=D1=82 =D0=BF=D0=B8=D1=81=D1=8C=D0=BC=D0=B0 =D0=B2 =\r\n",
-                "=D1=83=D0=BD=D0=B8=D0=BA=D0=BE=D0=B4=D0=B5"
+                "Se lo standard =F0=9F=93=AC fosse stato pi=C3=B9 semplice avremmo finito mo=\r\n",
+                "lto prima."
             )
             .as_bytes()
         );
@@ -562,21 +472,25 @@ mod test {
 
     #[test]
     fn base64_detect() {
-        let input = Body::new(vec![0, 1, 2, 3, 4, 5, 6, 7, 8, 9]);
+        let input = Body::new(vec![0; 80]);
         let encoding = input.encoding();
         assert_eq!(encoding, ContentTransferEncoding::Base64);
     }
 
     #[test]
     fn base64_encode_bytes() {
-        let encoded = Body::new_with_encoding(
-            vec![0, 1, 2, 3, 4, 5, 6, 7, 8, 9],
-            ContentTransferEncoding::Base64,
-        )
-        .unwrap();
+        let encoded =
+            Body::new_with_encoding(vec![0; 80], ContentTransferEncoding::Base64).unwrap();
 
         assert_eq!(encoded.encoding(), ContentTransferEncoding::Base64);
-        assert_eq!(encoded.as_ref(), b"AAECAwQFBgcICQ==");
+        assert_eq!(
+            encoded.as_ref(),
+            concat!(
+                "AAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA\r\n",
+                "AAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA="
+            )
+            .as_bytes()
+        );
     }
 
     #[test]

src/message/dkim.rs

@@ -1,14 +1,14 @@
 use std::{
     borrow::Cow,
     error::Error as StdError,
-    fmt::{self, Display, Write},
+    fmt::{self, Display},
     iter::IntoIterator,
     time::SystemTime,
 };
 
 use ed25519_dalek::Signer;
 use once_cell::sync::Lazy;
-use regex::{bytes::Regex as BRegex, Regex};
+use regex::bytes::Regex;
 use rsa::{pkcs1::DecodeRsaPrivateKey, Hash, PaddingScheme, RsaPrivateKey};
 use sha2::{Digest, Sha256};
 
@@ -96,9 +96,9 @@ impl Display for DkimSigningKeyError {
 impl StdError for DkimSigningKeyError {
     fn source(&self) -> Option<&(dyn StdError + 'static)> {
         Some(match &self.0 {
-            InnerDkimSigningKeyError::Base64(err) => &*err,
-            InnerDkimSigningKeyError::Rsa(err) => &*err,
-            InnerDkimSigningKeyError::Ed25519(err) => &*err,
+            InnerDkimSigningKeyError::Base64(err) => err,
+            InnerDkimSigningKeyError::Rsa(err) => err,
+            InnerDkimSigningKeyError::Ed25519(err) => err,
         })
     }
 }
@@ -115,12 +115,12 @@ enum InnerDkimSigningKey {
 
 impl DkimSigningKey {
     pub fn new(
-        private_key: String,
+        private_key: &str,
         algorithm: DkimSigningAlgorithm,
     ) -> Result<DkimSigningKey, DkimSigningKeyError> {
         Ok(Self(match algorithm {
             DkimSigningAlgorithm::Rsa => InnerDkimSigningKey::Rsa(
-                RsaPrivateKey::from_pkcs1_pem(&private_key)
+                RsaPrivateKey::from_pkcs1_pem(private_key)
                     .map_err(|err| DkimSigningKeyError(InnerDkimSigningKeyError::Rsa(err)))?,
             ),
             DkimSigningAlgorithm::Ed25519 => {
@@ -222,9 +222,9 @@ fn dkim_canonicalize_body(
     body: &[u8],
     canonicalization: DkimCanonicalizationType,
 ) -> Cow<'_, [u8]> {
-    static RE: Lazy<BRegex> = Lazy::new(|| BRegex::new("(\r\n)+$").unwrap());
-    static RE_DOUBLE_SPACE: Lazy<BRegex> = Lazy::new(|| BRegex::new("[\\t ]+").unwrap());
-    static RE_SPACE_EOL: Lazy<BRegex> = Lazy::new(|| BRegex::new("[\t ]\r\n").unwrap());
+    static RE: Lazy<Regex> = Lazy::new(|| Regex::new("(\r\n)+$").unwrap());
+    static RE_DOUBLE_SPACE: Lazy<Regex> = Lazy::new(|| Regex::new("[\\t ]+").unwrap());
+    static RE_SPACE_EOL: Lazy<Regex> = Lazy::new(|| Regex::new("[\t ]\r\n").unwrap());
     match canonicalization {
         DkimCanonicalizationType::Simple => RE.replace(body, &b"\r\n"[..]),
         DkimCanonicalizationType::Relaxed => {
@@ -241,23 +241,59 @@ fn dkim_canonicalize_body(
     }
 }
 
-/// Canonicalize the value of an header
-fn dkim_canonicalize_header_value(
-    value: &str,
-    canonicalization: DkimCanonicalizationType,
-) -> Cow<'_, str> {
-    match canonicalization {
-        DkimCanonicalizationType::Simple => Cow::Borrowed(value),
-        DkimCanonicalizationType::Relaxed => {
-            static RE_EOL: Lazy<Regex> = Lazy::new(|| Regex::new("\r\n").unwrap());
-            static RE_SPACES: Lazy<Regex> = Lazy::new(|| Regex::new("[\\t ]+").unwrap());
-            let value = RE_EOL.replace_all(value, "");
-            Cow::Owned(format!(
-                "{}\r\n",
-                RE_SPACES.replace_all(&value, " ").trim_end()
-            ))
+fn dkim_canonicalize_headers_relaxed(headers: &str) -> String {
+    let mut r = String::with_capacity(headers.len());
+
+    fn skip_whitespace(h: &str) -> &str {
+        match h.as_bytes().first() {
+            Some(b' ' | b'\t') => skip_whitespace(&h[1..]),
+            _ => h,
         }
     }
+
+    fn name(h: &str, out: &mut String) {
+        if let Some(name_end) = h.bytes().position(|c| c == b':') {
+            let (name, rest) = h.split_at(name_end + 1);
+            *out += name;
+            // Space after header colon is stripped.
+            value(skip_whitespace(rest), out);
+        } else {
+            // This should never happen.
+            *out += h;
+        }
+    }
+
+    fn value(h: &str, out: &mut String) {
+        match h.as_bytes() {
+            // Continuation lines.
+            [b'\r', b'\n', b' ' | b'\t', ..] => {
+                out.push(' ');
+                value(skip_whitespace(&h[2..]), out);
+            }
+            // End of header.
+            [b'\r', b'\n', ..] => {
+                *out += "\r\n";
+                name(&h[2..], out)
+            }
+            // Sequential whitespace.
+            [b' ' | b'\t', b' ' | b'\t' | b'\r', ..] => value(&h[1..], out),
+            // All whitespace becomes spaces.
+            [b'\t', ..] => {
+                out.push(' ');
+                value(&h[1..], out)
+            }
+            [_, ..] => {
+                let mut chars = h.chars();
+                out.push(chars.next().unwrap());
+                value(chars.as_str(), out)
+            }
+            [] => {}
+        }
+    }
+
+    name(headers, &mut r);
+
+    r
 }
 
 /// Canonicalize header tag
@@ -277,47 +313,35 @@ fn dkim_canonicalize_headers<'a>(
     mail_headers: &Headers,
     canonicalization: DkimCanonicalizationType,
 ) -> String {
+    let mut covered_headers = Headers::new();
+    for name in headers_list {
+        if let Some(h) = mail_headers.find_header(name) {
+            let name = dkim_canonicalize_header_tag(name, canonicalization);
+            covered_headers.insert_raw(HeaderValue::dangerous_new_pre_encoded(
+                HeaderName::new_from_ascii(name.into()).unwrap(),
+                h.get_raw().into(),
+                h.get_encoded().into(),
+            ));
+        }
+    }
+
+    let serialized = covered_headers.to_string();
+
     match canonicalization {
-        DkimCanonicalizationType::Simple => {
-            let mut signed_headers = Headers::new();
-
-            for h in headers_list {
-                let h = dkim_canonicalize_header_tag(h, canonicalization);
-                if let Some(value) = mail_headers.get_raw(&h) {
-                    signed_headers.insert_raw(HeaderValue::new(
-                        HeaderName::new_from_ascii(h.into()).unwrap(),
-                        dkim_canonicalize_header_value(value, canonicalization).to_string(),
-                    ))
-                }
-            }
-
-            signed_headers.to_string()
-        }
-        DkimCanonicalizationType::Relaxed => {
-            let mut signed_headers = String::new();
-
-            for h in headers_list {
-                let h = dkim_canonicalize_header_tag(h, canonicalization);
-                if let Some(value) = mail_headers.get_raw(&h) {
-                    write!(
-                        signed_headers,
-                        "{}:{}",
-                        h,
-                        dkim_canonicalize_header_value(value, canonicalization)
-                    )
-                    .expect("write implementation returned an error")
-                }
-            }
-
-            signed_headers
-        }
+        DkimCanonicalizationType::Simple => serialized,
+        DkimCanonicalizationType::Relaxed => dkim_canonicalize_headers_relaxed(&serialized),
     }
 }
 
 /// Sign with Dkim a message by adding Dkim-Signture header created with configuration expressed by
 /// dkim_config
-pub(super) fn dkim_sign(message: &mut Message, dkim_config: &DkimConfig) {
-    let timestamp = SystemTime::now()
+
+pub fn dkim_sign(message: &mut Message, dkim_config: &DkimConfig) {
+    dkim_sign_fixed_time(message, dkim_config, SystemTime::now())
+}
+
+fn dkim_sign_fixed_time(message: &mut Message, dkim_config: &DkimConfig, timestamp: SystemTime) {
+    let timestamp = timestamp
         .duration_since(SystemTime::UNIX_EPOCH)
         .unwrap()
         .as_secs();
@@ -385,21 +409,46 @@ pub(super) fn dkim_sign(message: &mut Message, dkim_config: &DkimConfig) {
 
 #[cfg(test)]
 mod test {
-    use std::{
-        io::Write,
-        process::{Command, Stdio},
-    };
+    use pretty_assertions::assert_eq;
 
     use super::{
         super::{
             header::{HeaderName, HeaderValue},
             Header, Message,
         },
-        dkim_canonicalize_body, dkim_canonicalize_header_value, dkim_canonicalize_headers,
+        dkim_canonicalize_headers, dkim_sign_fixed_time, DkimCanonicalization,
         DkimCanonicalizationType, DkimConfig, DkimSigningAlgorithm, DkimSigningKey,
     };
     use crate::StdError;
 
+    const KEY_RSA: &str = "-----BEGIN RSA PRIVATE KEY-----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+-----END RSA PRIVATE KEY-----";
+
     #[derive(Clone)]
     struct TestHeader(String);
 
@@ -417,47 +466,11 @@ mod test {
         }
     }
 
-    #[test]
-    fn test_body_simple_canonicalize() {
-        let body = b"test\r\n\r\ntest   \ttest\r\n\r\n\r\n";
-        let expected: &[u8] = b"test\r\n\r\ntest   \ttest\r\n";
-        assert_eq!(
-            dkim_canonicalize_body(body, DkimCanonicalizationType::Simple),
-            expected
-        )
-    }
-    #[test]
-    fn test_body_relaxed_canonicalize() {
-        let body = b"test\r\n\r\ntest   \ttest\r\n\r\n\r\n";
-        let expected: &[u8] = b"test\r\n\r\ntest test\r\n";
-        assert_eq!(
-            dkim_canonicalize_body(body, DkimCanonicalizationType::Relaxed),
-            expected
-        )
-    }
-    #[test]
-    fn test_header_simple_canonicalize() {
-        let value = "test\r\n\r\ntest   \ttest\r\n";
-        let expected = "test\r\n\r\ntest   \ttest\r\n";
-        assert_eq!(
-            dkim_canonicalize_header_value(value, DkimCanonicalizationType::Simple),
-            expected
-        )
-    }
-    #[test]
-    fn test_header_relaxed_canonicalize() {
-        let value = "test\r\n\r\ntest   \ttest\r\n";
-        let expected = "testtest test\r\n";
-        assert_eq!(
-            dkim_canonicalize_header_value(value, DkimCanonicalizationType::Relaxed),
-            expected
-        )
-    }
-
     fn test_message() -> Message {
         Message::builder()
-            .from("Test <test+ezrz@example.net>".parse().unwrap())
+            .from("Test O'Leary <test+ezrz@example.net>".parse().unwrap())
             .to("Test2 <test2@example.org>".parse().unwrap())
+            .date(std::time::UNIX_EPOCH)
             .header(TestHeader("test  test very very long with spaces and extra spaces   \twill be folded to several lines ".to_string()))
             .subject("Test with utf-8 ë")
             .body("test\r\n\r\ntest   \ttest\r\n\r\n\r\n".to_string()).unwrap()
@@ -466,63 +479,112 @@ mod test {
     #[test]
     fn test_headers_simple_canonicalize() {
         let message = test_message();
-        assert_eq!(dkim_canonicalize_headers(["From", "Test"], &message.headers, DkimCanonicalizationType::Simple),"From: Test <test+ezrz@example.net>\r\nTest: test  test very very long with spaces and extra spaces   \twill be \r\n folded to several lines \r\n")
+        dbg!(message.headers.to_string());
+        assert_eq!(dkim_canonicalize_headers(["From", "Test"], &message.headers, DkimCanonicalizationType::Simple), "From: =?utf-8?b?VGVzdCBPJ0xlYXJ5?= <test+ezrz@example.net>\r\nTest: test  test very very long with spaces and extra spaces   \twill be\r\n folded to several lines \r\n")
     }
+
     #[test]
     fn test_headers_relaxed_canonicalize() {
         let message = test_message();
-        assert_eq!(dkim_canonicalize_headers(["From", "Test"], &message.headers, DkimCanonicalizationType::Relaxed),"from:Test <test+ezrz@example.net>\r\ntest:test test very very long with spaces and extra spaces will be folded to several lines\r\n")
+        dbg!(message.headers.to_string());
+        assert_eq!(dkim_canonicalize_headers(["From", "Test"], &message.headers, DkimCanonicalizationType::Relaxed),"from:=?utf-8?b?VGVzdCBPJ0xlYXJ5?= <test+ezrz@example.net>\r\ntest:test test very very long with spaces and extra spaces will be folded to several lines\r\n")
     }
+
     #[test]
-    fn test_signature_rsa() {
+    fn test_signature_rsa_simple() {
         let mut message = test_message();
-        let key = "-----BEGIN RSA PRIVATE KEY-----
-MIIEpAIBAAKCAQEAz+FHbM8BwkBBz/Ux5OYLQ5Bp1HVuCHTP6Rr3HXTnome/2cGl
-/ze0tsmmFbCjjsS89MXbMGs9xJhjv18LmL1N0UTllblOizzVjorQyN4RwBOfG34j
-7SS56pwzrA738Ry8FAbL5InPWEgVzbOhXuTCs8yuzcqTnm4sH/csnIl7cMWeQkVn
-1FR9LKMtUG0fjhDPkdX0jx3qTX1L3Z7a7gX6geY191yNd9i9DvE2/+wMigMYz1LA
-ts4alk2g86MQhtbjc8AOR7EC15hSw37/lmamlunYLa3wC+PzHNMA8sAfnmkgNvip
-ssjh8LnelD9qn+VtsjQB5ppkeQx3TcUPvz5z+QIDAQABAoIBAQCzRa5ZEbSMlumq
-s+PRaOox3CrIRHUd6c8bUlvmFVllX1++JRhInvvD3ubSMcD7cIMb/D1o5jMgheMP
-uKHBmQ+w91+e3W30+gOZp/EiKRDZupIuHXxSGKgUwZx2N3pvfr5b7viLIKWllpTn
-DpCNy251rIDbjGX97Tk0X+8jGBVSTCxtruGJR5a+hz4t9Z7bz7JjZWcRNJC+VA+Q
-ATjnV7AHO1WR+0tAdPJaHsRLI7drKFSqTYq0As+MksZ40p7T6blZW8NUXA09fJRn
-3mP2TZdWjjfBXZje026v4T7TZl+TELKw5WirL/UJ8Zw8dGGV6EZvbfMacZuUB1YQ
-0vZnGe4BAoGBAO63xWP3OV8oLAMF90umuusPaQNSc6DnpjnP+sTAcXEYJA0Sa4YD
-y8dpTAdFJ4YvUQhLxtbZFK5Ih3x7ZhuerLSJiZiDPC2IJJb7j/812zQQriOi4mQ8
-bimxM4Nzql8FKGaXMppE5grFLsy8tw7neIM9KE4uwe9ajwJrRrOTUY8ZAoGBAN7t
-+xFeuhg4F9expyaPpCvKT2YNAdMcDzpm7GtLX292u+DQgBfg50Ur9XmbS+RPlx1W
-r2Sw3bTjRjJU9QnSZLL2w3hiii/wdaePI4SCaydHdLi4ZGz/pNUsUY+ck2pLptS0
-F7rL+s9MV9lUyhvX+pIh+O3idMWAdaymzs7ZlgfhAoGAVoFn2Wrscmw3Tr0puVNp
-JudFsbt+RU/Mr+SLRiNKuKX74nTLXBwiC1hAAd5wjTK2VaBIJPEzilikKFr7TIT6
-ps20e/0KoKFWSRROQTh9/+cPg8Bx88rmTNt3BGq00Ywn8M1XvAm9pyd/Zxf36kG9
-LSnLYlGVW6xgaIsBau+2vXkCgYAeChVdxtTutIhJ8U9ju9FUcUN3reMEDnDi3sGW
-x6ZJf8dbSN0p2o1vXbgLNejpD+x98JNbzxVg7Ysk9xu5whb9opC+ZRDX2uAPvxL7
-JRPJTDCnP3mQ0nXkn78xydh3Z1BIsyfLbPcT/eaMi4dcbyL9lARWEcDIaEHzDNsr
-NlioIQKBgQCXIZp5IBfG5WSXzFk8xvP4BUwHKEI5bttClBmm32K+vaSz8qO6ak6G
-4frg+WVopFg3HBHdK9aotzPEd0eHMXJv3C06Ynt2lvF+Rgi/kwGbkuq/mFVnmYYR
-Fz0TZ6sKrTAF3fdkN3bcQv6JG1CfnWENDGtekemwcCEA9v46/RsOfg==
------END RSA PRIVATE KEY-----";
-        let signing_key = DkimSigningKey::new(key.to_string(), DkimSigningAlgorithm::Rsa).unwrap();
-        message.sign(&DkimConfig::default_config(
-            "dkimtest".to_string(),
-            "example.org".to_string(),
-            signing_key,
-        ));
-        println!("{}", std::str::from_utf8(&message.formatted()).unwrap());
-        let mut verify_command = Command::new("dkimverify")
-            .stdin(Stdio::piped())
-            .spawn()
-            .expect("Fail to verify message signature");
-        let mut stdin = verify_command.stdin.take().expect("Failed to open stdin");
-        std::thread::spawn(move || {
-            stdin
-                .write_all(&message.formatted())
-                .expect("Failed to write to stdin");
-        });
-        assert!(verify_command
-            .wait()
-            .expect("Command did not run")
-            .success());
+        let signing_key = DkimSigningKey::new(KEY_RSA, DkimSigningAlgorithm::Rsa).unwrap();
+        dkim_sign_fixed_time(
+            &mut message,
+            &DkimConfig::new(
+                "dkimtest".to_string(),
+                "example.org".to_string(),
+                signing_key,
+                vec![
+                    HeaderName::new_from_ascii_str("Date"),
+                    HeaderName::new_from_ascii_str("From"),
+                    HeaderName::new_from_ascii_str("Subject"),
+                    HeaderName::new_from_ascii_str("To"),
+                ],
+                DkimCanonicalization {
+                    header: DkimCanonicalizationType::Simple,
+                    body: DkimCanonicalizationType::Simple,
+                },
+            ),
+            std::time::UNIX_EPOCH,
+        );
+        let signed = message.formatted();
+        let signed = std::str::from_utf8(&signed).unwrap();
+        assert_eq!(
+            signed,
+            std::concat!(
+                "From: =?utf-8?b?VGVzdCBPJ0xlYXJ5?= <test+ezrz@example.net>\r\n",
+                "To: Test2 <test2@example.org>\r\n",
+                "Date: Thu, 01 Jan 1970 00:00:00 +0000\r\n",
+                "Test: test  test very very long with spaces and extra spaces   \twill be\r\n",
+                " folded to several lines \r\n",
+                "Subject: Test with utf-8 =?utf-8?b?w6s=?=\r\n",
+                "Content-Transfer-Encoding: 7bit\r\n",
+                "DKIM-Signature: v=1; a=rsa-sha256; d=example.org; s=dkimtest;\r\n",
+                " c=simple/simple; q=dns/txt; t=0; h=Date:From:Subject:To;\r\n",
+                " bh=f3Zksdcjqa/xRBwdyFzIXWCcgP7XTgxjCgYsXOMKQl4=;\r\n",
+                " b=NhoIMMAALoSgu5lKAR0+MUQunOWnU7wpF9ORUFtpxq9sGZDo9AX43AMhFemyM5W204jpFwMU6pm7AMR1nOYBdSYye4yUALtvT2nqbJBwSh7JeYu+z22t1RFKp7qQR1il8aSrkbZuNMFHYuSEwW76QtKwcNqP4bQOzS9CzgQp0ABu8qwYPBr/EypykPTfqjtyN+ywrfdqjjGOzTpRGolH0hc3CrAETNjjHbNBgKgucXmXTN7hMRdzqWjeFPxizXwouwNAavFClPG0l33gXVArFWn+CkgA84G/s4zuJiF7QPZR87Pu4pw/vIlSXxH4a42W3tT19v9iBTH7X7ldYegtmQ==\r\n",
+                "\r\n",
+                "test\r\n",
+                "\r\n",
+                "test   \ttest\r\n",
+                "\r\n",
+                "\r\n",
+            )
+        );
+    }
+
+    #[test]
+    fn test_signature_rsa_relaxed() {
+        let mut message = test_message();
+        let signing_key = DkimSigningKey::new(KEY_RSA, DkimSigningAlgorithm::Rsa).unwrap();
+        dkim_sign_fixed_time(
+            &mut message,
+            &DkimConfig::new(
+                "dkimtest".to_string(),
+                "example.org".to_string(),
+                signing_key,
+                vec![
+                    HeaderName::new_from_ascii_str("Date"),
+                    HeaderName::new_from_ascii_str("From"),
+                    HeaderName::new_from_ascii_str("Subject"),
+                    HeaderName::new_from_ascii_str("To"),
+                ],
+                DkimCanonicalization {
+                    header: DkimCanonicalizationType::Relaxed,
+                    body: DkimCanonicalizationType::Relaxed,
+                },
+            ),
+            std::time::UNIX_EPOCH,
+        );
+        let signed = message.formatted();
+        let signed = std::str::from_utf8(&signed).unwrap();
+        println!("{}", signed);
+        assert_eq!(
+            signed,
+            std::concat!(
+                "From: =?utf-8?b?VGVzdCBPJ0xlYXJ5?= <test+ezrz@example.net>\r\n",
+                "To: Test2 <test2@example.org>\r\n",
+                "Date: Thu, 01 Jan 1970 00:00:00 +0000\r\n",
+                "Test: test  test very very long with spaces and extra spaces   \twill be\r\n",
+                " folded to several lines \r\n","Subject: Test with utf-8 =?utf-8?b?w6s=?=\r\n",
+                "Content-Transfer-Encoding: 7bit\r\n",
+                "DKIM-Signature: v=1; a=rsa-sha256; d=example.org; s=dkimtest;\r\n",
+                " c=relaxed/relaxed; q=dns/txt; t=0; h=date:from:subject:to;\r\n",
+                " bh=qN8je6qJgWFGSnN2MycC/XKPbN6BOrMJyAX2h4m19Ss=;\r\n",
+                " b=YaVfmH8dbGEywoLJ4uhbvYqDyQG1UGKFH3PE7zXGgk+YFxUgkwWjoA3aQupDNQtfTjfUsNe0dnrjyZP+ylnESpZBpbCIf5/n3FEh6j3RQthqNbQblcfH/U8mazTuRbVjYBbTZQDaQCMPTz+8D+ZQfXo2oq6dGzTuGvmuYft0CVsq/BIp/EkhZHqiphDeVJSHD4iKW8+L2XwEWThoY92xOYc1G0TtBwz2UJgtiHX2YulH/kRBHeK3dKn9RTNVL3VZ+9ZrnFwIhET9TPGtU2I+q0EMSWF9H9bTrASMgW/U+E0VM2btqJlrTU6rQ7wlQeHdwecLnzXcyhCUInF1+veMNw==\r\n",
+                "\r\n",
+                "test\r\n",
+                "\r\n",
+                "test   \ttest\r\n",
+                "\r\n",
+                "\r\n",
+            )
+        );
     }
 }

src/message/header/content.rs

@@ -75,6 +75,8 @@ impl Default for ContentTransferEncoding {
 
 #[cfg(test)]
 mod test {
+    use pretty_assertions::assert_eq;
+
     use super::ContentTransferEncoding;
     use crate::message::header::{HeaderName, HeaderValue, Headers};
 

src/message/header/content_disposition.rs

@@ -77,6 +77,8 @@ impl Header for ContentDisposition {
 
 #[cfg(test)]
 mod test {
+    use pretty_assertions::assert_eq;
+
     use super::ContentDisposition;
     use crate::message::header::{HeaderName, HeaderValue, Headers};
 

src/message/header/content_type.rs

@@ -149,6 +149,8 @@ mod serde {
 
 #[cfg(test)]
 mod test {
+    use pretty_assertions::assert_eq;
+
     use super::ContentType;
     use crate::message::header::{HeaderName, HeaderValue, Headers};
 

src/message/header/date.rs

@@ -8,7 +8,7 @@ use crate::BoxError;
 /// Message `Date` header
 ///
 /// Defined in [RFC2822](https://tools.ietf.org/html/rfc2822#section-3.3)
-#[derive(Debug, Clone, Copy, PartialEq)]
+#[derive(Debug, Clone, Copy, PartialEq, Eq)]
 pub struct Date(HttpDate);
 
 impl Date {
@@ -32,11 +32,11 @@ impl Header for Date {
 
     fn parse(s: &str) -> Result<Self, BoxError> {
         let mut s = String::from(s);
-        if s.ends_with(" -0000") {
+        if s.ends_with("+0000") {
             // The httpdate crate expects the `Date` to end in ` GMT`, but email
-            // uses `-0000`, so we crudely fix this issue here.
+            // uses `+0000` to indicate UTC, so we crudely fix this issue here.
 
-            s.truncate(s.len() - "-0000".len());
+            s.truncate(s.len() - "+0000".len());
             s.push_str("GMT");
         }
 
@@ -49,9 +49,9 @@ impl Header for Date {
             // The httpdate crate always appends ` GMT` to the end of the string,
             // but this is considered an obsolete date format for email
             // https://tools.ietf.org/html/rfc2822#appendix-A.6.2,
-            // so we replace `GMT` with `-0000`
+            // so we replace `GMT` with `+0000`
             val.truncate(val.len() - "GMT".len());
-            val.push_str("-0000");
+            val.push_str("+0000");
         }
 
         HeaderValue::dangerous_new_pre_encoded(Self::name(), val.clone(), val)
@@ -74,6 +74,8 @@ impl From<Date> for SystemTime {
 mod test {
     use std::time::{Duration, SystemTime};
 
+    use pretty_assertions::assert_eq;
+
     use super::Date;
     use crate::message::header::{HeaderName, HeaderValue, Headers};
 
@@ -88,7 +90,7 @@ mod test {
 
         assert_eq!(
             headers.to_string(),
-            "Date: Tue, 15 Nov 1994 08:12:31 -0000\r\n".to_string()
+            "Date: Tue, 15 Nov 1994 08:12:31 +0000\r\n".to_string()
         );
 
         // Tue, 15 Nov 1994 08:12:32 GMT
@@ -98,7 +100,7 @@ mod test {
 
         assert_eq!(
             headers.to_string(),
-            "Date: Tue, 15 Nov 1994 08:12:32 -0000\r\n"
+            "Date: Tue, 15 Nov 1994 08:12:32 +0000\r\n"
         );
     }
 
@@ -108,7 +110,7 @@ mod test {
 
         headers.insert_raw(HeaderValue::new(
             HeaderName::new_from_ascii_str("Date"),
-            "Tue, 15 Nov 1994 08:12:31 -0000".to_string(),
+            "Tue, 15 Nov 1994 08:12:31 +0000".to_string(),
         ));
 
         assert_eq!(
@@ -120,7 +122,7 @@ mod test {
 
         headers.insert_raw(HeaderValue::new(
             HeaderName::new_from_ascii_str("Date"),
-            "Tue, 15 Nov 1994 08:12:32 -0000".to_string(),
+            "Tue, 15 Nov 1994 08:12:32 +0000".to_string(),
         ));
 
         assert_eq!(

src/message/header/mailbox.rs

@@ -14,7 +14,7 @@ pub trait MailboxesHeader {
 macro_rules! mailbox_header {
     ($(#[$doc:meta])*($type_name: ident, $header_name: expr)) => {
         $(#[$doc])*
-        #[derive(Debug, Clone, PartialEq)]
+        #[derive(Debug, Clone, PartialEq, Eq)]
         pub struct $type_name(Mailbox);
 
         impl Header for $type_name {
@@ -56,7 +56,7 @@ macro_rules! mailbox_header {
 macro_rules! mailboxes_header {
     ($(#[$doc:meta])*($type_name: ident, $header_name: expr)) => {
         $(#[$doc])*
-        #[derive(Debug, Clone, PartialEq)]
+        #[derive(Debug, Clone, PartialEq, Eq)]
         pub struct $type_name(pub(crate) Mailboxes);
 
         impl MailboxesHeader for $type_name {
@@ -172,6 +172,8 @@ mailboxes_header! {
 
 #[cfg(test)]
 mod test {
+    use pretty_assertions::assert_eq;
+
     use super::{From, Mailbox, Mailboxes};
     use crate::message::header::{HeaderName, HeaderValue, Headers};
 
@@ -296,4 +298,31 @@ mod test {
 
         assert_eq!(headers.get::<From>(), Some(From(from.into())));
     }
+
+    #[test]
+    fn parse_multi_with_name_containing_comma() {
+        let from: Vec<Mailbox> = vec![
+            "Test, test <1@example.com>".parse().unwrap(),
+            "Test2, test2 <2@example.com>".parse().unwrap(),
+        ];
+
+        let mut headers = Headers::new();
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("From"),
+            "Test, test <1@example.com>, Test2, test2 <2@example.com>".to_string(),
+        ));
+
+        assert_eq!(headers.get::<From>(), Some(From(from.into())));
+    }
+
+    #[test]
+    fn parse_multi_with_name_containing_comma_last_broken() {
+        let mut headers = Headers::new();
+        headers.insert_raw(HeaderValue::new(
+            HeaderName::new_from_ascii_str("From"),
+            "Test, test <1@example.com>, Test2, test2".to_string(),
+        ));
+
+        assert_eq!(headers.get::<From>(), None);
+    }
 }

src/message/header/mod.rs

@@ -3,10 +3,12 @@
 use std::{
     borrow::Cow,
     error::Error,
-    fmt::{self, Display, Formatter},
+    fmt::{self, Display, Formatter, Write},
     ops::Deref,
 };
 
+use email_encoding::headers::EmailWriter;
+
 pub use self::{
     content::*,
     content_disposition::ContentDisposition,
@@ -121,7 +123,7 @@ impl Headers {
         self.find_header_index(name).map(|i| self.headers.remove(i))
     }
 
-    fn find_header(&self, name: &str) -> Option<&HeaderValue> {
+    pub(crate) fn find_header(&self, name: &str) -> Option<&HeaderValue> {
         self.headers
             .iter()
             .find(|value| name.eq_ignore_ascii_case(&value.name))
@@ -275,6 +277,7 @@ impl PartialEq<HeaderName> for &str {
     }
 }
 
+/// A safe for use header value
 #[derive(Debug, Clone, PartialEq)]
 pub struct HeaderValue {
     name: HeaderName,
@@ -283,6 +286,12 @@ pub struct HeaderValue {
 }
 
 impl HeaderValue {
+    /// Construct a new `HeaderValue` and encode it
+    ///
+    /// Takes the header `name` and the `raw_value` and encodes
+    /// it via `RFC2047` and line folds it.
+    ///
+    /// [`RFC2047`]: https://datatracker.ietf.org/doc/html/rfc2047
     pub fn new(name: HeaderName, raw_value: String) -> Self {
         let mut encoded_value = String::with_capacity(raw_value.len());
         HeaderValueEncoder::encode(&name, &raw_value, &mut encoded_value).unwrap();
@@ -294,6 +303,14 @@ impl HeaderValue {
         }
     }
 
+    /// Construct a new `HeaderValue` using a pre-encoded header value
+    ///
+    /// This method is _extremely_ dangerous as it opens up
+    /// the encoder to header injection attacks, but is sometimes
+    /// acceptable for use if `encoded_value` contains only ascii
+    /// printable characters and is already line folded.
+    ///
+    /// When in doubt use [`HeaderValue::new`].
     pub fn dangerous_new_pre_encoded(
         name: HeaderName,
         raw_value: String,
@@ -305,57 +322,46 @@ impl HeaderValue {
             encoded_value,
         }
     }
+
+    pub(crate) fn get_raw(&self) -> &str {
+        &self.raw_value
+    }
+
+    pub(crate) fn get_encoded(&self) -> &str {
+        &self.encoded_value
+    }
 }
 
-const ENCODING_START_PREFIX: &str = "=?utf-8?b?";
-const ENCODING_END_SUFFIX: &str = "?=";
-const MAX_LINE_LEN: usize = 76;
-
 /// [RFC 1522](https://tools.ietf.org/html/rfc1522) header value encoder
-struct HeaderValueEncoder {
-    line_len: usize,
+struct HeaderValueEncoder<'a> {
+    writer: EmailWriter<'a>,
     encode_buf: String,
 }
 
-impl HeaderValueEncoder {
-    fn encode(name: &str, value: &str, f: &mut impl fmt::Write) -> fmt::Result {
-        let (words_iter, encoder) = Self::new(name, value);
-        encoder.format(words_iter, f)
+impl<'a> HeaderValueEncoder<'a> {
+    fn encode(name: &str, value: &'a str, f: &'a mut impl fmt::Write) -> fmt::Result {
+        let (words_iter, encoder) = Self::new(name, value, f);
+        encoder.format(words_iter)
     }
 
-    fn new<'a>(name: &str, value: &'a str) -> (WordsPlusFillIterator<'a>, Self) {
+    fn new(
+        name: &str,
+        value: &'a str,
+        writer: &'a mut dyn Write,
+    ) -> (WordsPlusFillIterator<'a>, Self) {
+        let line_len = name.len() + ": ".len();
+        let writer = EmailWriter::new(writer, line_len, false);
+
         (
             WordsPlusFillIterator { s: value },
             Self {
-                line_len: name.len() + ": ".len(),
+                writer,
                 encode_buf: String::new(),
             },
         )
     }
 
-    fn format(
-        mut self,
-        words_iter: WordsPlusFillIterator<'_>,
-        f: &mut impl fmt::Write,
-    ) -> fmt::Result {
-        /// Estimate if an encoded string of `len` would fix in an empty line
-        fn would_fit_new_line(len: usize) -> bool {
-            len < (MAX_LINE_LEN - " ".len())
-        }
-
-        /// Estimate how long a string of `len` would be after base64 encoding plus
-        /// adding the encoding prefix and suffix to it
-        fn base64_len(len: usize) -> usize {
-            ENCODING_START_PREFIX.len() + (len * 4 / 3 + 4) + ENCODING_END_SUFFIX.len()
-        }
-
-        /// Estimate how many more bytes we can fit in the current line
-        fn available_len_to_max_encode_len(len: usize) -> usize {
-            len.saturating_sub(
-                ENCODING_START_PREFIX.len() + (len * 3 / 4 + 4) + ENCODING_END_SUFFIX.len(),
-            )
-        }
-
+    fn format(mut self, words_iter: WordsPlusFillIterator<'_>) -> fmt::Result {
         for next_word in words_iter {
             let allowed = allowed_str(next_word);
 
@@ -363,161 +369,64 @@ impl HeaderValueEncoder {
                 // This word only contains allowed characters
 
                 // the next word is allowed, but we may have accumulated some words to encode
-                self.flush_encode_buf(f, true)?;
+                self.flush_encode_buf()?;
 
-                if next_word.len() > self.remaining_line_len() {
-                    // not enough space left on this line to encode word
-
-                    if self.something_written_to_this_line() && would_fit_new_line(next_word.len())
-                    {
-                        // word doesn't fit this line, but something had already been written to it,
-                        // and word would fit the next line, so go to a new line
-                        // so go to new line
-                        self.new_line(f)?;
-                    } else {
-                        // word neither fits this line and the next one, cut it
-                        // in the middle and make it fit
-
-                        let mut next_word = next_word;
-
-                        while !next_word.is_empty() {
-                            if self.remaining_line_len() == 0 {
-                                self.new_line(f)?;
-                            }
-
-                            let len = self.remaining_line_len().min(next_word.len());
-                            let first_part = &next_word[..len];
-                            next_word = &next_word[len..];
-
-                            f.write_str(first_part)?;
-                            self.line_len += first_part.len();
-                        }
-
-                        continue;
-                    }
-                }
-
-                // word fits, write it!
-                f.write_str(next_word)?;
-                self.line_len += next_word.len();
+                self.writer.folding().write_str(next_word)?;
             } else {
                 // This word contains unallowed characters
-
-                if self.remaining_line_len() >= base64_len(self.encode_buf.len() + next_word.len())
-                {
-                    // next_word fits
-                    self.encode_buf.push_str(next_word);
-                    continue;
-                }
-
-                // next_word doesn't fit this line
-
-                if would_fit_new_line(base64_len(next_word.len())) {
-                    // ...but it would fit the next one
-
-                    self.flush_encode_buf(f, false)?;
-                    self.new_line(f)?;
-
-                    self.encode_buf.push_str(next_word);
-                    continue;
-                }
-
-                // ...and also wouldn't fit the next one.
-                // chop it up into pieces
-
-                let mut next_word = next_word;
-
-                while !next_word.is_empty() {
-                    let mut len = available_len_to_max_encode_len(self.remaining_line_len())
-                        .min(next_word.len());
-
-                    if len == 0 {
-                        self.flush_encode_buf(f, false)?;
-                        self.new_line(f)?;
-                    }
-
-                    // avoid slicing on a char boundary
-                    while !next_word.is_char_boundary(len) {
-                        len += 1;
-                    }
-                    let first_part = &next_word[..len];
-                    next_word = &next_word[len..];
-
-                    self.encode_buf.push_str(first_part);
-                }
+                self.encode_buf.push_str(next_word);
             }
         }
 
-        self.flush_encode_buf(f, false)?;
+        self.flush_encode_buf()?;
 
         Ok(())
     }
 
-    /// Returns the number of bytes left for the current line
-    fn remaining_line_len(&self) -> usize {
-        MAX_LINE_LEN - self.line_len
-    }
-
-    /// Returns true if something has been written to the current line
-    fn something_written_to_this_line(&self) -> bool {
-        self.line_len > 1
-    }
-
-    fn flush_encode_buf(
-        &mut self,
-        f: &mut impl fmt::Write,
-        switching_to_allowed: bool,
-    ) -> fmt::Result {
+    fn flush_encode_buf(&mut self) -> fmt::Result {
         if self.encode_buf.is_empty() {
             // nothing to encode
             return Ok(());
         }
 
-        let mut write_after = None;
+        // It is important that we don't encode leading whitespace otherwise it breaks wrapping.
+        let first_not_allowed = self
+            .encode_buf
+            .bytes()
+            .enumerate()
+            .find(|(_i, c)| !allowed_char(*c))
+            .map(|(i, _)| i);
+        // May as well also write the tail in plain text.
+        let last_not_allowed = self
+            .encode_buf
+            .bytes()
+            .enumerate()
+            .rev()
+            .find(|(_i, c)| !allowed_char(*c))
+            .map(|(i, _)| i + 1);
 
-        if switching_to_allowed {
-            // If the next word only contains allowed characters, and the string to encode
-            // ends with a space, take the space out of the part to encode
+        let (prefix, to_encode, suffix) = match first_not_allowed {
+            Some(first_not_allowed) => {
+                let last_not_allowed = last_not_allowed.unwrap();
 
-            let last_char = self.encode_buf.pop().expect("self.encode_buf isn't empty");
-            if is_space_like(last_char) {
-                write_after = Some(last_char);
-            } else {
-                self.encode_buf.push(last_char);
+                let (remaining, suffix) = self.encode_buf.split_at(last_not_allowed);
+                let (prefix, to_encode) = remaining.split_at(first_not_allowed);
+
+                (prefix, to_encode, suffix)
             }
-        }
+            None => ("", self.encode_buf.as_str(), ""),
+        };
 
-        f.write_str(ENCODING_START_PREFIX)?;
-        let encoded = base64::display::Base64Display::with_config(
-            self.encode_buf.as_bytes(),
-            base64::STANDARD,
-        );
-        write!(f, "{}", encoded)?;
-        f.write_str(ENCODING_END_SUFFIX)?;
-
-        self.line_len += ENCODING_START_PREFIX.len();
-        self.line_len += self.encode_buf.len() * 4 / 3 + 4;
-        self.line_len += ENCODING_END_SUFFIX.len();
-
-        if let Some(write_after) = write_after {
-            f.write_char(write_after)?;
-            self.line_len += 1;
-        }
+        self.writer.folding().write_str(prefix)?;
+        email_encoding::headers::rfc2047::encode(to_encode, &mut self.writer)?;
+        self.writer.folding().write_str(suffix)?;
 
         self.encode_buf.clear();
         Ok(())
     }
-
-    fn new_line(&mut self, f: &mut impl fmt::Write) -> fmt::Result {
-        f.write_str("\r\n ")?;
-        self.line_len = 1;
-
-        Ok(())
-    }
 }
 
-/// Iterator yielding a string split space by space, but including all space
-/// characters between it and the next word
+/// Iterator yielding a string split by space, but spaces are included before the next word.
 struct WordsPlusFillIterator<'a> {
     s: &'a str,
 }
@@ -532,35 +441,31 @@ impl<'a> Iterator for WordsPlusFillIterator<'a> {
 
         let next_word = self
             .s
-            .char_indices()
+            .bytes()
+            .enumerate()
             .skip(1)
-            .skip_while(|&(_i, c)| !is_space_like(c))
-            .find(|&(_i, c)| !is_space_like(c))
-            .map(|(i, _)| i);
+            .find(|&(_i, c)| c == b' ')
+            .map(|(i, _)| i)
+            .unwrap_or(self.s.len());
 
-        let word = &self.s[..next_word.unwrap_or(self.s.len())];
+        let word = &self.s[..next_word];
         self.s = &self.s[word.len()..];
         Some(word)
     }
 }
 
-const fn is_space_like(c: char) -> bool {
-    c == ',' || c == ' '
-}
-
 fn allowed_str(s: &str) -> bool {
-    s.chars().all(allowed_char)
+    s.bytes().all(allowed_char)
 }
 
-const fn allowed_char(c: char) -> bool {
-    c >= 1 as char && c <= 9 as char
-        || c == 11 as char
-        || c == 12 as char
-        || c >= 14 as char && c <= 127 as char
+const fn allowed_char(c: u8) -> bool {
+    c >= 1 && c <= 9 || c == 11 || c == 12 || c >= 14 && c <= 127
 }
 
 #[cfg(test)]
 mod tests {
+    use pretty_assertions::assert_eq;
+
     use super::{HeaderName, HeaderValue, Headers};
 
     #[test]
@@ -644,8 +549,8 @@ mod tests {
         assert_eq!(
             headers.to_string(),
             concat!(
-                "To: Ascii <example@example.com>, John Doe <johndoe@example.com, John Smith \r\n",
-                " <johnsmith@example.com>, Pinco Pallino <pincopallino@example.com>, Jemand \r\n",
+                "To: Ascii <example@example.com>, John Doe <johndoe@example.com, John Smith\r\n",
+                " <johnsmith@example.com>, Pinco Pallino <pincopallino@example.com>, Jemand\r\n",
                 " <jemand@example.com>, Jean Dupont <jean@example.com>\r\n"
             )
         );
@@ -662,8 +567,8 @@ mod tests {
         assert_eq!(
             headers.to_string(),
             concat!(
-                "Subject: Hello! This is lettre, and this \r\n ",
-                "IsAVeryLongLineDoYouKnowWhatsGoingToHappenIGuessWeAreGoingToFindOut. Ok I \r\n",
+                "Subject: Hello! This is lettre, and this\r\n",
+                " IsAVeryLongLineDoYouKnowWhatsGoingToHappenIGuessWeAreGoingToFindOut. Ok I\r\n",
                 " guess that's it!\r\n"
             )
         );
@@ -681,8 +586,9 @@ mod tests {
         assert_eq!(
             headers.to_string(),
             concat!(
-                "Subject: Hello! IGuessTheLastLineWasntLongEnoughSoLetsTryAgainShallWeWhatDoY\r\n",
-                " ouThinkItsGoingToHappenIGuessWereAboutToFindOut! I don't know\r\n",
+                "Subject: Hello!\r\n",
+                " IGuessTheLastLineWasntLongEnoughSoLetsTryAgainShallWeWhatDoYouThinkItsGoingToHappenIGuessWereAboutToFindOut!\r\n",
+                " I don't know\r\n",
             )
         );
     }
@@ -697,11 +603,7 @@ mod tests {
 
         assert_eq!(
             headers.to_string(),
-            concat!(
-                "Subject: 1abcdefghijklmnopqrstuvwxyz2abcdefghijklmnopqrstuvwxyz3abcdefghijkl\r\n",
-                " mnopqrstuvwxyz4abcdefghijklmnopqrstuvwxyz5abcdefghijklmnopqrstuvwxyz6abcdef\r\n",
-                " ghijklmnopqrstuvwxyz\r\n",
-            )
+            "Subject: 1abcdefghijklmnopqrstuvwxyz2abcdefghijklmnopqrstuvwxyz3abcdefghijklmnopqrstuvwxyz4abcdefghijklmnopqrstuvwxyz5abcdefghijklmnopqrstuvwxyz6abcdefghijklmnopqrstuvwxyz\r\n",
         );
     }
 
@@ -715,7 +617,7 @@ mod tests {
 
         assert_eq!(
             headers.to_string(),
-            "To: =?utf-8?b?U2XDoW4=?= <sean@example.com>\r\n"
+            "To: Se=?utf-8?b?w6E=?=n <sean@example.com>\r\n"
         );
     }
 
@@ -744,11 +646,11 @@ mod tests {
         assert_eq!(
             headers.to_string(),
             concat!(
-                "To: =?utf-8?b?8J+MjQ==?= <world@example.com>, =?utf-8?b?8J+mhg==?= \r\n",
-                " Everywhere <ducks@example.com>, =?utf-8?b?0JjQstCw0L3QvtCyIA==?=\r\n",
-                " =?utf-8?b?0JjQstCw0L0g0JjQstCw0L3QvtCy0LjRhw==?= <ivanov@example.com>, \r\n",
-                " =?utf-8?b?SsSBbmlzIELEk3J6acWGxaE=?= <janis@example.com>, \r\n",
-                " =?utf-8?b?U2XDoW4gw5MgUnVkYcOt?= <sean@example.com>\r\n"
+                "To: =?utf-8?b?8J+MjQ==?= <world@example.com>, =?utf-8?b?8J+mhg==?= Everywhere\r\n",
+                " <ducks@example.com>, =?utf-8?b?0JjQstCw0L3QvtCyINCY0LLQsNC9INCY0LLQsNC9?=\r\n",
+                " =?utf-8?b?0L7QstC40Yc=?= <ivanov@example.com>, J=?utf-8?b?xIFuaXMgQsST?=\r\n",
+                " =?utf-8?b?cnppxYbFoQ==?= <janis@example.com>, Se=?utf-8?b?w6FuIMOTIFJ1?=\r\n",
+                " =?utf-8?b?ZGHDrQ==?= <sean@example.com>\r\n",
             )
         );
     }
@@ -764,7 +666,14 @@ mod tests {
 
         assert_eq!(
             headers.to_string(),
-            "Subject: =?utf-8?b?8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz?=\r\n"
+            concat!(
+                "Subject: =?utf-8?b?8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz?=\r\n",
+                " =?utf-8?b?8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbM=?=\r\n",
+                " =?utf-8?b?8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbM=?=\r\n",
+                " =?utf-8?b?8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbM=?=\r\n",
+                " =?utf-8?b?8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+ls/CfpbM=?=\r\n",
+                " =?utf-8?b?8J+ls/CfpbPwn6Wz8J+ls/CfpbPwn6Wz8J+lsw==?=\r\n"
+            )
         );
     }
 
@@ -809,14 +718,14 @@ mod tests {
         assert_eq!(
             headers.to_string(),
             concat!(
-                "Subject: Hello! This is lettre, and this \r\n",
-                " IsAVeryLongLineDoYouKnowWhatsGoingToHappenIGuessWeAreGoingToFindOut. Ok I \r\n",
+                "Subject: Hello! This is lettre, and this\r\n",
+                " IsAVeryLongLineDoYouKnowWhatsGoingToHappenIGuessWeAreGoingToFindOut. Ok I\r\n",
                 " guess that's it!\r\n",
-                "To: =?utf-8?b?8J+MjQ==?= <world@example.com>, =?utf-8?b?8J+mhg==?= \r\n",
-                " Everywhere <ducks@example.com>, =?utf-8?b?0JjQstCw0L3QvtCyIA==?=\r\n",
-                " =?utf-8?b?0JjQstCw0L0g0JjQstCw0L3QvtCy0LjRhw==?= <ivanov@example.com>, \r\n",
-                " =?utf-8?b?SsSBbmlzIELEk3J6acWGxaE=?= <janis@example.com>, \r\n",
-                " =?utf-8?b?U2XDoW4gw5MgUnVkYcOt?= <sean@example.com>\r\n",
+                "To: =?utf-8?b?8J+MjQ==?= <world@example.com>, =?utf-8?b?8J+mhg==?= Everywhere\r\n",
+                " <ducks@example.com>, =?utf-8?b?0JjQstCw0L3QvtCyINCY0LLQsNC9INCY0LLQsNC9?=\r\n",
+                " =?utf-8?b?0L7QstC40Yc=?= <ivanov@example.com>, J=?utf-8?b?xIFuaXMgQsST?=\r\n",
+                " =?utf-8?b?cnppxYbFoQ==?= <janis@example.com>, Se=?utf-8?b?w6FuIMOTIFJ1?=\r\n",
+                " =?utf-8?b?ZGHDrQ==?= <sean@example.com>\r\n",
                 "From: Someone <somewhere@example.com>\r\n",
                 "Content-Transfer-Encoding: quoted-printable\r\n",
             )
@@ -834,8 +743,8 @@ mod tests {
         assert_eq!(
             headers.to_string(),
             concat!(
-                "Subject: =?utf-8?b?77yL5Luu5ZCN?= :a;go; \r\n",
-                " =?utf-8?b?Ozs7OztzOzs7Ozs7Ozs7Ozs7Ozs7O2ZmZmVpbm1qZ2dnZ2dnZ2dn772G44Gj?=\r\n"
+                "Subject: =?utf-8?b?77yL5Luu5ZCN?= :a;go;\r\n",
+                " ;;;;;s;;;;;;;;;;;;;;;;fffeinmjggggggggg=?utf-8?b?772G44Gj?=\r\n"
             )
         );
     }

src/message/header/special.rs

@@ -4,7 +4,7 @@ use crate::{
 };
 
 /// Message format version, defined in [RFC2045](https://tools.ietf.org/html/rfc2045#section-4)
-#[derive(Debug, Copy, Clone, PartialEq)]
+#[derive(Debug, Copy, Clone, PartialEq, Eq)]
 pub struct MimeVersion {
     major: u8,
     minor: u8,
@@ -16,15 +16,18 @@ pub struct MimeVersion {
 pub const MIME_VERSION_1_0: MimeVersion = MimeVersion::new(1, 0);
 
 impl MimeVersion {
+    /// Build a new `MimeVersion` header
     pub const fn new(major: u8, minor: u8) -> Self {
         MimeVersion { major, minor }
     }
 
+    /// Get the `major` value of this `MimeVersion` header.
     #[inline]
     pub const fn major(self) -> u8 {
         self.major
     }
 
+    /// Get the `minor` value of this `MimeVersion` header.
     #[inline]
     pub const fn minor(self) -> u8 {
         self.minor
@@ -64,6 +67,8 @@ impl Default for MimeVersion {
 
 #[cfg(test)]
 mod test {
+    use pretty_assertions::assert_eq;
+
     use super::{MimeVersion, MIME_VERSION_1_0};
     use crate::message::header::{HeaderName, HeaderValue, Headers};
 

src/message/header/textual.rs

@@ -4,7 +4,7 @@ use crate::BoxError;
 macro_rules! text_header {
     ($(#[$attr:meta])* Header($type_name: ident, $header_name: expr )) => {
         $(#[$attr])*
-        #[derive(Debug, Clone, PartialEq)]
+        #[derive(Debug, Clone, PartialEq, Eq)]
         pub struct $type_name(String);
 
         impl Header for $type_name {
@@ -85,6 +85,8 @@ text_header! {
 
 #[cfg(test)]
 mod test {
+    use pretty_assertions::assert_eq;
+
     use super::Subject;
     use crate::message::header::{HeaderName, HeaderValue, Headers};
 

src/message/mailbox/serde.rs

@@ -154,6 +154,7 @@ impl<'de> Deserialize<'de> for Mailboxes {
 
 #[cfg(test)]
 mod test {
+    use pretty_assertions::assert_eq;
     use serde_json::from_str;
 
     use super::*;

src/message/mailbox/types.rs

@@ -315,6 +315,18 @@ impl From<Mailboxes> for Vec<Mailbox> {
     }
 }
 
+impl FromIterator<Mailbox> for Mailboxes {
+    fn from_iter<T: IntoIterator<Item = Mailbox>>(iter: T) -> Self {
+        Self(Vec::from_iter(iter))
+    }
+}
+
+impl Extend<Mailbox> for Mailboxes {
+    fn extend<T: IntoIterator<Item = Mailbox>>(&mut self, iter: T) {
+        self.0.extend(iter);
+    }
+}
+
 impl IntoIterator for Mailboxes {
     type Item = Mailbox;
     type IntoIter = ::std::vec::IntoIter<Mailbox>;
@@ -324,14 +336,6 @@ impl IntoIterator for Mailboxes {
     }
 }
 
-impl Extend<Mailbox> for Mailboxes {
-    fn extend<T: IntoIterator<Item = Mailbox>>(&mut self, iter: T) {
-        for elem in iter {
-            self.0.push(elem);
-        }
-    }
-}
-
 impl Display for Mailboxes {
     fn fmt(&self, f: &mut Formatter<'_>) -> FmtResult {
         let mut iter = self.iter();
@@ -352,11 +356,37 @@ impl Display for Mailboxes {
 impl FromStr for Mailboxes {
     type Err = AddressError;
 
-    fn from_str(src: &str) -> Result<Self, Self::Err> {
-        src.split(',')
-            .map(|m| m.trim().parse())
-            .collect::<Result<Vec<_>, _>>()
-            .map(Mailboxes)
+    fn from_str(mut src: &str) -> Result<Self, Self::Err> {
+        let mut mailboxes = Vec::new();
+
+        if !src.is_empty() {
+            // n-1 elements
+            let mut skip = 0;
+            while let Some(i) = src[skip..].find(',') {
+                let left = &src[..skip + i];
+
+                match left.trim().parse() {
+                    Ok(mailbox) => {
+                        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))
     }
 }
 
@@ -445,6 +475,8 @@ fn write_quoted_string_char(f: &mut Formatter<'_>, c: u8) -> FmtResult {
 mod test {
     use std::convert::TryInto;
 
+    use pretty_assertions::assert_eq;
+
     use super::Mailbox;
 
     #[test]

src/message/mimebody.rs

@@ -398,6 +398,8 @@ impl EmailFormat for MultiPart {
 
 #[cfg(test)]
 mod test {
+    use pretty_assertions::assert_eq;
+
     use super::*;
     use crate::message::header;
 
@@ -477,7 +479,7 @@ mod test {
         assert_eq!(
             String::from_utf8(part.formatted()).unwrap(),
             concat!(
-                "Content-Type: multipart/mixed; \r\n",
+                "Content-Type: multipart/mixed;\r\n",
                 " boundary=\"0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\"\r\n",
                 "\r\n",
                 "--0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\r\n",
@@ -524,8 +526,8 @@ mod test {
         assert_eq!(
             String::from_utf8(part.formatted()).unwrap(),
             concat!(
-                "Content-Type: multipart/encrypted; \r\n",
-                " boundary=\"0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\"; \r\n",
+                "Content-Type: multipart/encrypted;\r\n",
+                " boundary=\"0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\";\r\n",
                 " protocol=\"application/pgp-encrypted\"\r\n",
                 "\r\n",
                 "--0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\r\n",
@@ -580,8 +582,8 @@ mod test {
         assert_eq!(
             String::from_utf8(part.formatted()).unwrap(),
             concat!(
-                "Content-Type: multipart/signed; \r\n",
-                " boundary=\"0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\"; \r\n",
+                "Content-Type: multipart/signed;\r\n",
+                " boundary=\"0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\";\r\n",
                 " protocol=\"application/pgp-signature\";",
                 " micalg=\"pgp-sha256\"\r\n",
                 "\r\n",
@@ -622,7 +624,7 @@ mod test {
                              .body(String::from("<p>Текст <em>письма</em> в <a href=\"https://ru.wikipedia.org/wiki/Юникод\">уникоде</a><p>")));
 
         assert_eq!(String::from_utf8(part.formatted()).unwrap(),
-                   concat!("Content-Type: multipart/alternative; \r\n",
+                   concat!("Content-Type: multipart/alternative;\r\n",
                            " boundary=\"0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\"\r\n",
                            "\r\n",
                            "--0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\r\n",
@@ -660,11 +662,11 @@ mod test {
                              .body(String::from("int main() { return 0; }")));
 
         assert_eq!(String::from_utf8(part.formatted()).unwrap(),
-                   concat!("Content-Type: multipart/mixed; \r\n",
+                   concat!("Content-Type: multipart/mixed;\r\n",
                            " boundary=\"0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\"\r\n",
                            "\r\n",
                            "--0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\r\n",
-                           "Content-Type: multipart/related; \r\n",
+                           "Content-Type: multipart/related;\r\n",
                            " boundary=\"0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\"\r\n",
                            "\r\n",
                            "--0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1\r\n",

src/message/mod.rs

@@ -232,6 +232,7 @@ trait EmailFormat {
 pub struct MessageBuilder {
     headers: Headers,
     envelope: Option<Envelope>,
+    drop_bcc: bool,
 }
 
 impl MessageBuilder {
@@ -240,24 +241,26 @@ impl MessageBuilder {
         Self {
             headers: Headers::new(),
             envelope: None,
+            drop_bcc: true,
         }
     }
 
-    /// Set custom header to message
-    pub fn header<H: Header>(mut self, header: H) -> Self {
-        self.headers.set(header);
-        self
+    /// Set or add mailbox to `From` header
+    ///
+    /// Defined in [RFC5322](https://tools.ietf.org/html/rfc5322#section-3.6.2).
+    ///
+    /// Shortcut for `self.mailbox(header::From(mbox))`.
+    pub fn from(self, mbox: Mailbox) -> Self {
+        self.mailbox(header::From::from(Mailboxes::from(mbox)))
     }
 
-    /// Add mailbox to header
-    pub fn mailbox<H: Header + MailboxesHeader>(self, header: H) -> Self {
-        match self.headers.get::<H>() {
-            Some(mut header_) => {
-                header_.join_mailboxes(header);
-                self.header(header_)
-            }
-            None => self.header(header),
-        }
+    /// Set `Sender` header. Should be used when providing several `From` mailboxes.
+    ///
+    /// Defined in [RFC5322](https://tools.ietf.org/html/rfc5322#section-3.6.2).
+    ///
+    /// Shortcut for `self.header(header::Sender(mbox))`.
+    pub fn sender(self, mbox: Mailbox) -> Self {
+        self.header(header::Sender::from(mbox))
     }
 
     /// Add `Date` header to message
@@ -275,41 +278,6 @@ impl MessageBuilder {
         self.date(SystemTime::now())
     }
 
-    /// Set `Subject` header to message
-    ///
-    /// Shortcut for `self.header(header::Subject(subject.into()))`.
-    pub fn subject<S: Into<String>>(self, subject: S) -> Self {
-        let s: String = subject.into();
-        self.header(header::Subject::from(s))
-    }
-
-    /// Set `MIME-Version` header to 1.0
-    ///
-    /// Shortcut for `self.header(header::MIME_VERSION_1_0)`.
-    ///
-    /// Not exposed as it is set by body methods
-    fn mime_1_0(self) -> Self {
-        self.header(header::MIME_VERSION_1_0)
-    }
-
-    /// Set `Sender` header. Should be used when providing several `From` mailboxes.
-    ///
-    /// Defined in [RFC5322](https://tools.ietf.org/html/rfc5322#section-3.6.2).
-    ///
-    /// Shortcut for `self.header(header::Sender(mbox))`.
-    pub fn sender(self, mbox: Mailbox) -> Self {
-        self.header(header::Sender::from(mbox))
-    }
-
-    /// Set or add mailbox to `From` header
-    ///
-    /// Defined in [RFC5322](https://tools.ietf.org/html/rfc5322#section-3.6.2).
-    ///
-    /// Shortcut for `self.mailbox(header::From(mbox))`.
-    pub fn from(self, mbox: Mailbox) -> Self {
-        self.mailbox(header::From::from(Mailboxes::from(mbox)))
-    }
-
     /// Set or add mailbox to `ReplyTo` header
     ///
     /// Defined in [RFC5322](https://tools.ietf.org/html/rfc5322#section-3.6.2).
@@ -352,6 +320,14 @@ impl MessageBuilder {
         self.header(header::References::from(id))
     }
 
+    /// Set `Subject` header to message
+    ///
+    /// Shortcut for `self.header(header::Subject(subject.into()))`.
+    pub fn subject<S: Into<String>>(self, subject: S) -> Self {
+        let s: String = subject.into();
+        self.header(header::Subject::from(s))
+    }
+
     /// Set [Message-ID
     /// header](https://tools.ietf.org/html/rfc5322#section-3.6.4)
     ///
@@ -385,12 +361,43 @@ impl MessageBuilder {
         self.header(header::UserAgent::from(id))
     }
 
+    /// Set custom header to message
+    pub fn header<H: Header>(mut self, header: H) -> Self {
+        self.headers.set(header);
+        self
+    }
+
+    /// Add mailbox to header
+    pub fn mailbox<H: Header + MailboxesHeader>(self, header: H) -> Self {
+        match self.headers.get::<H>() {
+            Some(mut header_) => {
+                header_.join_mailboxes(header);
+                self.header(header_)
+            }
+            None => self.header(header),
+        }
+    }
+
     /// Force specific envelope (by default it is derived from headers)
     pub fn envelope(mut self, envelope: Envelope) -> Self {
         self.envelope = Some(envelope);
         self
     }
 
+    /// Keep the `Bcc` header
+    ///
+    /// By default the `Bcc` header is removed from the email after
+    /// using it to generate the message envelope. In some cases though,
+    /// like when saving the email as an `.eml`, or sending through
+    /// some transports (like the Gmail API) that don't take a separate
+    /// envelope value, it becomes necessary to keep the `Bcc` header.
+    ///
+    /// Calling this method overrides the default behaviour.
+    pub fn keep_bcc(mut self) -> Self {
+        self.drop_bcc = false;
+        self
+    }
+
     // TODO: High-level methods for attachments and embedded files
 
     /// Create message from body
@@ -423,8 +430,10 @@ impl MessageBuilder {
             None => Envelope::try_from(&res.headers)?,
         };
 
-        // Remove `Bcc` headers now the envelope is set
-        res.headers.remove::<header::Bcc>();
+        if res.drop_bcc {
+            // Remove `Bcc` headers now the envelope is set
+            res.headers.remove::<header::Bcc>();
+        }
 
         Ok(Message {
             headers: res.headers,
@@ -455,6 +464,15 @@ impl MessageBuilder {
     pub fn singlepart(self, part: SinglePart) -> Result<Message, EmailError> {
         self.mime_1_0().build(MessageBody::Mime(Part::Single(part)))
     }
+
+    /// Set `MIME-Version` header to 1.0
+    ///
+    /// Shortcut for `self.header(header::MIME_VERSION_1_0)`.
+    ///
+    /// Not exposed as it is set by body methods
+    fn mime_1_0(self) -> Self {
+        self.header(header::MIME_VERSION_1_0)
+    }
 }
 
 /// Email message which can be formatted
@@ -550,7 +568,7 @@ impl Message {
     /// JcaBbL6ZSBIMA3AdaIjtvNRiomueHqh0GspTgOeCE2585TSFnw6vEOJ8RlR4A0Mw
     /// I45fbR4l+3D/30WMfZlM6bzZbwPXEnr2s1mirmuQpjumY9wLhK25
     /// -----END RSA PRIVATE KEY-----";
-    /// let signing_key = DkimSigningKey::new(key.to_string(), DkimSigningAlgorithm::Rsa).unwrap();
+    /// let signing_key = DkimSigningKey::new(key, DkimSigningAlgorithm::Rsa).unwrap();
     /// message.sign(&DkimConfig::default_config(
     ///     "dkimtest".to_string(),
     ///     "example.org".to_string(),
@@ -598,6 +616,8 @@ fn make_message_id() -> String {
 mod test {
     use std::time::{Duration, SystemTime};
 
+    use pretty_assertions::assert_eq;
+
     use super::{header, mailbox::Mailbox, make_message_id, Message, MultiPart, SinglePart};
 
     #[test]
@@ -626,7 +646,7 @@ mod test {
     }
 
     #[test]
-    fn email_message() {
+    fn email_message_no_bcc() {
         // Tue, 15 Nov 1994 08:12:31 GMT
         let date = SystemTime::UNIX_EPOCH + Duration::from_secs(784887151);
 
@@ -650,10 +670,48 @@ mod test {
         assert_eq!(
             String::from_utf8(email.formatted()).unwrap(),
             concat!(
-                "Date: Tue, 15 Nov 1994 08:12:31 -0000\r\n",
+                "Date: Tue, 15 Nov 1994 08:12:31 +0000\r\n",
                 "From: =?utf-8?b?0JrQsNC4?= <kayo@example.com>\r\n",
                 "To: \"Pony O.P.\" <pony@domain.tld>\r\n",
-                "Subject: =?utf-8?b?0Y/So9CwINC10Lsg0LHQtdC705nQvSE=?=\r\n",
+                "Subject: =?utf-8?b?0Y/So9CwINC10Lsg0LHQtdC705nQvQ==?=!\r\n",
+                "Content-Transfer-Encoding: 7bit\r\n",
+                "\r\n",
+                "Happy new year!"
+            )
+        );
+    }
+
+    #[test]
+    fn email_message_keep_bcc() {
+        // Tue, 15 Nov 1994 08:12:31 GMT
+        let date = SystemTime::UNIX_EPOCH + Duration::from_secs(784887151);
+
+        let email = Message::builder()
+            .date(date)
+            .bcc("hidden@example.com".parse().unwrap())
+            .keep_bcc()
+            .header(header::From(
+                vec![Mailbox::new(
+                    Some("Каи".into()),
+                    "kayo@example.com".parse().unwrap(),
+                )]
+                .into(),
+            ))
+            .header(header::To(
+                vec!["Pony O.P. <pony@domain.tld>".parse().unwrap()].into(),
+            ))
+            .header(header::Subject::from(String::from("яңа ел белән!")))
+            .body(String::from("Happy new year!"))
+            .unwrap();
+
+        assert_eq!(
+            String::from_utf8(email.formatted()).unwrap(),
+            concat!(
+                "Date: Tue, 15 Nov 1994 08:12:31 +0000\r\n",
+                "Bcc: hidden@example.com\r\n",
+                "From: =?utf-8?b?0JrQsNC4?= <kayo@example.com>\r\n",
+                "To: \"Pony O.P.\" <pony@domain.tld>\r\n",
+                "Subject: =?utf-8?b?0Y/So9CwINC10Lsg0LHQtdC705nQvQ==?=!\r\n",
                 "Content-Transfer-Encoding: 7bit\r\n",
                 "\r\n",
                 "Happy new year!"

src/transport/smtp/async_transport.rs

@@ -198,6 +198,9 @@ where
 {
     fn clone(&self) -> Self {
         Self {
+            #[cfg(feature = "pool")]
+            inner: Arc::clone(&self.inner),
+            #[cfg(not(feature = "pool"))]
             inner: self.inner.clone(),
         }
     }

src/transport/smtp/authentication.rs

@@ -98,12 +98,12 @@ impl Mechanism {
                 let decoded_challenge = challenge
                     .ok_or_else(|| error::client("This mechanism does expect a challenge"))?;
 
-                if vec!["User Name", "Username:", "Username"].contains(&decoded_challenge) {
-                    return Ok(credentials.authentication_identity.to_string());
+                if ["User Name", "Username:", "Username"].contains(&decoded_challenge) {
+                    return Ok(credentials.authentication_identity.clone());
                 }
 
-                if vec!["Password", "Password:"].contains(&decoded_challenge) {
-                    return Ok(credentials.secret.to_string());
+                if ["Password", "Password:"].contains(&decoded_challenge) {
+                    return Ok(credentials.secret.clone());
                 }
 
                 Err(error::client("Unrecognized challenge"))

src/transport/smtp/client/async_connection.rs

@@ -1,4 +1,4 @@
-use std::{fmt::Display, time::Duration};
+use std::{fmt::Display, net::IpAddr, time::Duration};
 
 use futures_util::io::{AsyncBufReadExt, AsyncWriteExt, BufReader};
 
@@ -8,7 +8,7 @@ use super::{AsyncNetworkStream, ClientCodec, TlsParameters};
 use crate::{
     transport::smtp::{
         authentication::{Credentials, Mechanism},
-        commands::*,
+        commands::{Auth, Data, Ehlo, Mail, Noop, Quit, Rcpt, Starttls},
         error,
         error::Error,
         extension::{ClientId, Extension, MailBodyParameter, MailParameter, ServerInfo},
@@ -41,6 +41,7 @@ pub struct AsyncSmtpConnection {
 }
 
 impl AsyncSmtpConnection {
+    /// Get information about the server
     pub fn server_info(&self) -> &ServerInfo {
         &self.server_info
     }
@@ -54,8 +55,11 @@ impl AsyncSmtpConnection {
         timeout: Option<Duration>,
         hello_name: &ClientId,
         tls_parameters: Option<TlsParameters>,
+        local_address: Option<IpAddr>,
     ) -> Result<AsyncSmtpConnection, Error> {
-        let stream = AsyncNetworkStream::connect_tokio1(server, timeout, tls_parameters).await?;
+        let stream =
+            AsyncNetworkStream::connect_tokio1(server, timeout, tls_parameters, local_address)
+                .await?;
         Self::connect_impl(stream, hello_name).await
     }
 

src/transport/smtp/client/async_net.rs

@@ -1,6 +1,6 @@
 use std::{
     io, mem,
-    net::SocketAddr,
+    net::{IpAddr, SocketAddr},
     pin::Pin,
     task::{Context, Poll},
     time::Duration,
@@ -19,7 +19,10 @@ use futures_rustls::client::TlsStream as AsyncStd1RustlsTlsStream;
 #[cfg(feature = "tokio1")]
 use tokio1_crate::io::{AsyncRead as _, AsyncWrite as _, ReadBuf as Tokio1ReadBuf};
 #[cfg(feature = "tokio1")]
-use tokio1_crate::net::{TcpStream as Tokio1TcpStream, ToSocketAddrs as Tokio1ToSocketAddrs};
+use tokio1_crate::net::{
+    TcpSocket as Tokio1TcpSocket, TcpStream as Tokio1TcpStream,
+    ToSocketAddrs as Tokio1ToSocketAddrs,
+};
 #[cfg(feature = "tokio1-native-tls")]
 use tokio1_native_tls_crate::TlsStream as Tokio1TlsStream;
 #[cfg(feature = "tokio1-rustls-tls")]
@@ -33,6 +36,8 @@ use tokio1_rustls::client::TlsStream as Tokio1RustlsTlsStream;
 ))]
 use super::InnerTlsParameters;
 use super::TlsParameters;
+#[cfg(feature = "tokio1")]
+use crate::transport::smtp::client::net::resolved_address_filter;
 use crate::transport::smtp::{error, Error};
 
 /// A network stream
@@ -109,44 +114,59 @@ impl AsyncNetworkStream {
         server: T,
         timeout: Option<Duration>,
         tls_parameters: Option<TlsParameters>,
+        local_addr: Option<IpAddr>,
     ) -> Result<AsyncNetworkStream, Error> {
-        async fn try_connect_timeout<T: Tokio1ToSocketAddrs>(
+        async fn try_connect<T: Tokio1ToSocketAddrs>(
             server: T,
-            timeout: Duration,
+            timeout: Option<Duration>,
+            local_addr: Option<IpAddr>,
         ) -> Result<Tokio1TcpStream, Error> {
             let addrs = tokio1_crate::net::lookup_host(server)
                 .await
-                .map_err(error::connection)?;
+                .map_err(error::connection)?
+                .filter(|resolved_addr| resolved_address_filter(resolved_addr, local_addr));
 
             let mut last_err = None;
 
             for addr in addrs {
-                let connect_future = Tokio1TcpStream::connect(&addr);
-                match tokio1_crate::time::timeout(timeout, connect_future).await {
-                    Ok(Ok(stream)) => return Ok(stream),
-                    Ok(Err(err)) => last_err = Some(err),
-                    Err(_) => {
-                        last_err = Some(io::Error::new(
-                            io::ErrorKind::TimedOut,
-                            "connection timed out",
-                        ))
+                let socket = match addr.ip() {
+                    IpAddr::V4(_) => Tokio1TcpSocket::new_v4(),
+                    IpAddr::V6(_) => Tokio1TcpSocket::new_v6(),
+                }
+                .map_err(error::connection)?;
+                if let Some(local_addr) = local_addr {
+                    socket
+                        .bind(SocketAddr::new(local_addr, 0))
+                        .map_err(error::connection)?;
+                }
+
+                let connect_future = socket.connect(addr);
+                if let Some(timeout) = timeout {
+                    match tokio1_crate::time::timeout(timeout, connect_future).await {
+                        Ok(Ok(stream)) => return Ok(stream),
+                        Ok(Err(err)) => last_err = Some(err),
+                        Err(_) => {
+                            last_err = Some(io::Error::new(
+                                io::ErrorKind::TimedOut,
+                                "connection timed out",
+                            ))
+                        }
+                    }
+                } else {
+                    match connect_future.await {
+                        Ok(stream) => return Ok(stream),
+                        Err(err) => last_err = Some(err),
                     }
                 }
             }
 
             Err(match last_err {
                 Some(last_err) => error::connection(last_err),
-                None => error::connection("could not resolve to any address"),
+                None => error::connection("could not resolve to any supported address"),
             })
         }
 
-        let tcp_stream = match timeout {
-            Some(t) => try_connect_timeout(server, t).await?,
-            None => Tokio1TcpStream::connect(server)
-                .await
-                .map_err(error::connection)?,
-        };
-
+        let tcp_stream = try_connect(server, timeout, local_addr).await?;
         let mut stream = AsyncNetworkStream::new(InnerAsyncNetworkStream::Tokio1Tcp(tcp_stream));
         if let Some(tls_parameters) = tls_parameters {
             stream.upgrade_tls(tls_parameters).await?;
@@ -160,6 +180,9 @@ 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
+        // Whilst we can create a AsyncStd1TcpStream from an existing socket, it needs to first have
+        // connected which is a blocking operation.
         async fn try_connect_timeout<T: AsyncStd1ToSocketAddrs>(
             server: T,
             timeout: Duration,

src/transport/smtp/client/connection.rs

@@ -1,7 +1,7 @@
 use std::{
     fmt::Display,
     io::{self, BufRead, BufReader, Write},
-    net::ToSocketAddrs,
+    net::{IpAddr, ToSocketAddrs},
     time::Duration,
 };
 
@@ -12,7 +12,7 @@ use crate::{
     address::Envelope,
     transport::smtp::{
         authentication::{Credentials, Mechanism},
-        commands::*,
+        commands::{Auth, Data, Ehlo, Mail, Noop, Quit, Rcpt, Starttls},
         error,
         error::Error,
         extension::{ClientId, Extension, MailBodyParameter, MailParameter, ServerInfo},
@@ -44,6 +44,7 @@ pub struct SmtpConnection {
 }
 
 impl SmtpConnection {
+    /// Get information about the server
     pub fn server_info(&self) -> &ServerInfo {
         &self.server_info
     }
@@ -58,8 +59,9 @@ impl SmtpConnection {
         timeout: Option<Duration>,
         hello_name: &ClientId,
         tls_parameters: Option<&TlsParameters>,
+        local_address: Option<IpAddr>,
     ) -> Result<SmtpConnection, Error> {
-        let stream = NetworkStream::connect(server, timeout, tls_parameters)?;
+        let stream = NetworkStream::connect(server, timeout, tls_parameters, local_address)?;
         let stream = BufReader::new(stream);
         let mut conn = SmtpConnection {
             stream,

src/transport/smtp/client/mod.rs

@@ -12,7 +12,7 @@
 //! };
 //!
 //! let hello = ClientId::Domain("my_hostname".to_string());
-//! let mut client = SmtpConnection::connect(&("localhost", SMTP_PORT), None, &hello, None)?;
+//! let mut client = SmtpConnection::connect(&("localhost", SMTP_PORT), None, &hello, None, None)?;
 //! client.command(Mail::new(Some("user@example.com".parse()?), vec![]))?;
 //! client.command(Rcpt::new("user@example.org".parse()?, vec![]))?;
 //! client.command(Data)?;

src/transport/smtp/client/net.rs

@@ -1,7 +1,8 @@
 use std::{
     io::{self, Read, Write},
     mem,
-    net::{Ipv4Addr, Shutdown, SocketAddr, SocketAddrV4, TcpStream, ToSocketAddrs},
+    net::{IpAddr, Ipv4Addr, Shutdown, SocketAddr, SocketAddrV4, TcpStream, ToSocketAddrs},
+    sync::Arc,
     time::Duration,
 };
 
@@ -9,6 +10,7 @@ use std::{
 use native_tls::TlsStream;
 #[cfg(feature = "rustls-tls")]
 use rustls::{ClientConnection, ServerName, StreamOwned};
+use socket2::{Domain, Protocol, Type};
 
 #[cfg(any(feature = "native-tls", feature = "rustls-tls"))]
 use super::InnerTlsParameters;
@@ -83,19 +85,39 @@ impl NetworkStream {
         server: T,
         timeout: Option<Duration>,
         tls_parameters: Option<&TlsParameters>,
+        local_addr: Option<IpAddr>,
     ) -> Result<NetworkStream, Error> {
-        fn try_connect_timeout<T: ToSocketAddrs>(
+        fn try_connect<T: ToSocketAddrs>(
             server: T,
-            timeout: Duration,
+            timeout: Option<Duration>,
+            local_addr: Option<IpAddr>,
         ) -> Result<TcpStream, Error> {
-            let addrs = server.to_socket_addrs().map_err(error::connection)?;
+            let addrs = server
+                .to_socket_addrs()
+                .map_err(error::connection)?
+                .filter(|resolved_addr| resolved_address_filter(resolved_addr, local_addr));
 
             let mut last_err = None;
 
             for addr in addrs {
-                match TcpStream::connect_timeout(&addr, timeout) {
-                    Ok(stream) => return Ok(stream),
-                    Err(err) => last_err = Some(err),
+                let socket = socket2::Socket::new(
+                    Domain::for_address(addr),
+                    Type::STREAM,
+                    Some(Protocol::TCP),
+                )
+                .map_err(error::connection)?;
+                bind_local_address(&socket, &addr, local_addr)?;
+
+                if let Some(timeout) = timeout {
+                    match socket.connect_timeout(&addr.into(), timeout) {
+                        Ok(_) => return Ok(socket.into()),
+                        Err(err) => last_err = Some(err),
+                    }
+                } else {
+                    match socket.connect(&addr.into()) {
+                        Ok(_) => return Ok(socket.into()),
+                        Err(err) => last_err = Some(err),
+                    }
                 }
             }
 
@@ -105,11 +127,7 @@ impl NetworkStream {
             })
         }
 
-        let tcp_stream = match timeout {
-            Some(t) => try_connect_timeout(server, t)?,
-            None => TcpStream::connect(server).map_err(error::connection)?,
-        };
-
+        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)?;
@@ -158,8 +176,8 @@ 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(connector.clone(), domain).map_err(error::connection)?;
+                let connection = ClientConnection::new(Arc::clone(connector), domain)
+                    .map_err(error::connection)?;
                 let stream = StreamOwned::new(connection, tcp_stream);
                 InnerNetworkStream::RustlsTls(stream)
             }
@@ -289,3 +307,47 @@ impl Write for NetworkStream {
         }
     }
 }
+
+/// If the local address is set, binds the socket to this address.
+/// If local address is not set, then destination address is required to determine to the default
+/// local address on some platforms.
+/// See: https://github.com/hyperium/hyper/blob/faf24c6ad8eee1c3d5ccc9a4d4835717b8e2903f/src/client/connect/http.rs#L560
+fn bind_local_address(
+    socket: &socket2::Socket,
+    dst_addr: &SocketAddr,
+    local_addr: Option<IpAddr>,
+) -> Result<(), Error> {
+    match local_addr {
+        Some(local_addr) => {
+            socket
+                .bind(&SocketAddr::new(local_addr, 0).into())
+                .map_err(error::connection)?;
+        }
+        _ => {
+            if cfg!(windows) {
+                // Windows requires a socket be bound before calling connect
+                let any: SocketAddr = match dst_addr {
+                    SocketAddr::V4(_) => ([0, 0, 0, 0], 0).into(),
+                    SocketAddr::V6(_) => ([0, 0, 0, 0, 0, 0, 0, 0], 0).into(),
+                };
+                socket.bind(&any.into()).map_err(error::connection)?;
+            }
+        }
+    }
+    Ok(())
+}
+
+/// When we have an iterator of resolved remote addresses, we must filter them to be the same
+/// protocol as the local address binding. If no local address is set, then all will be matched.
+pub(crate) fn resolved_address_filter(
+    resolved_addr: &SocketAddr,
+    local_addr: Option<IpAddr>,
+) -> bool {
+    match local_addr {
+        Some(local_addr) => match resolved_addr.ip() {
+            IpAddr::V4(_) => local_addr.is_ipv4(),
+            IpAddr::V6(_) => local_addr.is_ipv6(),
+        },
+        None => true,
+    }
+}

src/transport/smtp/client/tls.rs

@@ -219,6 +219,7 @@ impl TlsParameters {
         TlsParametersBuilder::new(domain).build()
     }
 
+    /// Creates a new `TlsParameters` builder
     pub fn builder(domain: String) -> TlsParametersBuilder {
         TlsParametersBuilder::new(domain)
     }

src/transport/smtp/commands.rs

@@ -13,7 +13,7 @@ use crate::{
 };
 
 /// EHLO command
-#[derive(PartialEq, Clone, Debug)]
+#[derive(PartialEq, Eq, Clone, Debug)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 pub struct Ehlo {
     client_id: ClientId,
@@ -33,7 +33,7 @@ impl Ehlo {
 }
 
 /// STARTTLS command
-#[derive(PartialEq, Clone, Debug, Copy)]
+#[derive(PartialEq, Eq, Clone, Debug, Copy)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 pub struct Starttls;
 
@@ -44,7 +44,7 @@ impl Display for Starttls {
 }
 
 /// MAIL command
-#[derive(PartialEq, Clone, Debug)]
+#[derive(PartialEq, Eq, Clone, Debug)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 pub struct Mail {
     sender: Option<Address>,
@@ -73,7 +73,7 @@ impl Mail {
 }
 
 /// RCPT command
-#[derive(PartialEq, Clone, Debug)]
+#[derive(PartialEq, Eq, Clone, Debug)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 pub struct Rcpt {
     recipient: Address,
@@ -101,7 +101,7 @@ impl Rcpt {
 }
 
 /// DATA command
-#[derive(PartialEq, Clone, Debug, Copy)]
+#[derive(PartialEq, Eq, Clone, Debug, Copy)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 pub struct Data;
 
@@ -112,7 +112,7 @@ impl Display for Data {
 }
 
 /// QUIT command
-#[derive(PartialEq, Clone, Debug, Copy)]
+#[derive(PartialEq, Eq, Clone, Debug, Copy)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 pub struct Quit;
 
@@ -123,7 +123,7 @@ impl Display for Quit {
 }
 
 /// NOOP command
-#[derive(PartialEq, Clone, Debug, Copy)]
+#[derive(PartialEq, Eq, Clone, Debug, Copy)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 pub struct Noop;
 
@@ -134,7 +134,7 @@ impl Display for Noop {
 }
 
 /// HELP command
-#[derive(PartialEq, Clone, Debug)]
+#[derive(PartialEq, Eq, Clone, Debug)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 pub struct Help {
     argument: Option<String>,
@@ -158,7 +158,7 @@ impl Help {
 }
 
 /// VRFY command
-#[derive(PartialEq, Clone, Debug)]
+#[derive(PartialEq, Eq, Clone, Debug)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 pub struct Vrfy {
     argument: String,
@@ -178,7 +178,7 @@ impl Vrfy {
 }
 
 /// EXPN command
-#[derive(PartialEq, Clone, Debug)]
+#[derive(PartialEq, Eq, Clone, Debug)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 pub struct Expn {
     argument: String,
@@ -198,7 +198,7 @@ impl Expn {
 }
 
 /// RSET command
-#[derive(PartialEq, Clone, Debug, Copy)]
+#[derive(PartialEq, Eq, Clone, Debug, Copy)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 pub struct Rset;
 
@@ -209,7 +209,7 @@ impl Display for Rset {
 }
 
 /// AUTH command
-#[derive(PartialEq, Clone, Debug)]
+#[derive(PartialEq, Eq, Clone, Debug)]
 #[cfg_attr(feature = "serde", derive(serde::Serialize, serde::Deserialize))]
 pub struct Auth {
     mechanism: Mechanism,

src/transport/smtp/pool/async_impl.rs

@@ -158,14 +158,14 @@ impl<E: Executor> Pool<E> {
                     #[cfg(feature = "tracing")]
                     tracing::debug!("reusing a pooled connection");
 
-                    return Ok(PooledConnection::wrap(conn, self.clone()));
+                    return Ok(PooledConnection::wrap(conn, Arc::clone(self)));
                 }
                 None => {
                     #[cfg(feature = "tracing")]
                     tracing::debug!("creating a new connection");
 
                     let conn = self.client.connection().await?;
-                    return Ok(PooledConnection::wrap(conn, self.clone()));
+                    return Ok(PooledConnection::wrap(conn, Arc::clone(self)));
                 }
             }
         }

src/transport/smtp/pool/sync_impl.rs

@@ -141,14 +141,14 @@ impl Pool {
                     #[cfg(feature = "tracing")]
                     tracing::debug!("reusing a pooled connection");
 
-                    return Ok(PooledConnection::wrap(conn, self.clone()));
+                    return Ok(PooledConnection::wrap(conn, Arc::clone(self)));
                 }
                 None => {
                     #[cfg(feature = "tracing")]
                     tracing::debug!("creating a new connection");
 
                     let conn = self.client.connection()?;
-                    return Ok(PooledConnection::wrap(conn, self.clone()));
+                    return Ok(PooledConnection::wrap(conn, Arc::clone(self)));
                 }
             }
         }

src/transport/smtp/transport.rs

@@ -221,6 +221,7 @@ impl SmtpClient {
             self.info.timeout,
             &self.info.hello_name,
             tls_parameters,
+            None,
         )?;
 
         #[cfg(any(feature = "native-tls", feature = "rustls-tls"))]

src/transport/smtp/util.rs

@@ -41,7 +41,7 @@ mod tests {
         ]
         .iter()
         {
-            assert_eq!(format!("{}", XText(input)), expect.to_string());
+            assert_eq!(format!("{}", XText(input)), (*expect).to_string());
         }
     }
 }

src/transport/stub/mod.rs

@@ -53,6 +53,8 @@ use futures_util::lock::Mutex as FuturesMutex;
 use crate::AsyncTransport;
 use crate::{address::Envelope, Transport};
 
+/// An error returned by the stub transport
+#[non_exhaustive]
 #[derive(Debug, Copy, Clone)]
 pub struct Error;
 

testdata/email_with_png.eml

@@ -1,10 +1,10 @@
-Date: Tue, 15 Nov 1994 08:12:31 -0000
+Date: Tue, 15 Nov 1994 08:12:31 +0000
 From: NoBody <nobody@domain.tld>
 Reply-To: Yuin <yuin@domain.tld>
 To: Hei <hei@domain.tld>
 Subject: Happy new year
 MIME-Version: 1.0
-Content-Type: multipart/related; 
+Content-Type: multipart/related;
  boundary="GUEEoEeTXtLcK2sMhmH1RfC1co13g4rtnRUFjQFA"
 
 --0oVZ2r6AoLAhLlb0gPNSKy6BEqdS2IfwxrcbUuo1

tests/transport_file.rs

@@ -43,7 +43,7 @@ mod sync {
                 "Reply-To: Yuin <yuin@domain.tld>\r\n",
                 "To: Hei <hei@domain.tld>\r\n",
                 "Subject: Happy new year\r\n",
-                "Date: Tue, 15 Nov 1994 08:12:31 -0000\r\n",
+                "Date: Tue, 15 Nov 1994 08:12:31 +0000\r\n",
                 "Content-Transfer-Encoding: 7bit\r\n",
                 "\r\n",
                 "Be happy!"
@@ -81,7 +81,7 @@ mod sync {
                 "Reply-To: Yuin <yuin@domain.tld>\r\n",
                 "To: Hei <hei@domain.tld>\r\n",
                 "Subject: Happy new year\r\n",
-                "Date: Tue, 15 Nov 1994 08:12:31 -0000\r\n",
+                "Date: Tue, 15 Nov 1994 08:12:31 +0000\r\n",
                 "Content-Transfer-Encoding: 7bit\r\n",
                 "\r\n",
                 "Be happy!"
@@ -141,7 +141,7 @@ mod tokio_1 {
                 "Reply-To: Yuin <yuin@domain.tld>\r\n",
                 "To: Hei <hei@domain.tld>\r\n",
                 "Subject: Happy new year\r\n",
-                "Date: Tue, 15 Nov 1994 08:12:31 -0000\r\n",
+                "Date: Tue, 15 Nov 1994 08:12:31 +0000\r\n",
                 "Content-Transfer-Encoding: 7bit\r\n",
                 "\r\n",
                 "Be happy!"
@@ -192,7 +192,7 @@ mod asyncstd_1 {
                 "Reply-To: Yuin <yuin@domain.tld>\r\n",
                 "To: Hei <hei@domain.tld>\r\n",
                 "Subject: Happy new year\r\n",
-                "Date: Tue, 15 Nov 1994 08:12:31 -0000\r\n",
+                "Date: Tue, 15 Nov 1994 08:12:31 +0000\r\n",
                 "Content-Transfer-Encoding: 7bit\r\n",
                 "\r\n",
                 "Be happy!"

tests/transport_stub.rs

@@ -18,7 +18,7 @@ mod sync {
         sender_ok.send(&email).unwrap();
         sender_ko.send(&email).unwrap_err();
 
-        let expected_messages = vec![(
+        let expected_messages = [(
             email.envelope().clone(),
             String::from_utf8(email.formatted()).unwrap(),
         )];
@@ -47,7 +47,7 @@ mod tokio_1 {
         sender_ok.send(email.clone()).await.unwrap();
         sender_ko.send(email.clone()).await.unwrap_err();
 
-        let expected_messages = vec![(
+        let expected_messages = [(
             email.envelope().clone(),
             String::from_utf8(email.formatted()).unwrap(),
         )];
@@ -75,7 +75,7 @@ mod asyncstd_1 {
         sender_ok.send(email.clone()).await.unwrap();
         sender_ko.send(email.clone()).await.unwrap_err();
 
-        let expected_messages = vec![(
+        let expected_messages = [(
             email.envelope().clone(),
             String::from_utf8(email.formatted()).unwrap(),
         )];