daaki_smtp/connection/

helpers.rs

//! Private helpers: validation, MAIL FROM / RCPT TO building, EHLO,
//! pipelining, error handling, and internal implementation methods.
//!
//! RFC 5321 (SMTP), RFC 1870 (SIZE), RFC 6152 (8BITMIME), RFC 6531 (SMTPUTF8),
//! RFC 3030 (CHUNKING/BINARYMIME), RFC 3461 (DSN), RFC 4954 (AUTH params),
//! RFC 8689 (REQUIRETLS), RFC 4865 (FUTURERELEASE), RFC 2852 (DELIVERBY),
//! RFC 6758 (MT-PRIORITY).

#[allow(clippy::wildcard_imports)]
use super::*;

impl SmtpConnection {
    // -----------------------------------------------------------------------
    // Private helpers
    // -----------------------------------------------------------------------

    /// Validate that an encoded command line does not exceed the 512-octet
    /// limit (RFC 5321 Section 4.5.3.1.4).
    ///
    /// `line_len` is the number of bytes in the command line including the
    /// terminating CRLF. `cmd_name` is used in the error message.
    ///
    /// For MAIL FROM, use [`validate_mail_from_line_length`] instead —
    /// ESMTP extensions increase the limit beyond 512.
    pub(super) fn validate_command_line_length(
        line_len: usize,
        cmd_name: &str,
    ) -> Result<(), Error> {
        if line_len > Self::SMTP_MAX_COMMAND_LINE {
            return Err(Error::Protocol(format!(
                "{cmd_name} command line exceeds {}-octet limit ({line_len} octets) \
                 (RFC 5321 Section 4.5.3.1.4)",
                Self::SMTP_MAX_COMMAND_LINE
            )));
        }
        Ok(())
    }

    /// Validate that a MAIL FROM command line does not exceed the
    /// ESMTP-extended limit (RFC 5321 Section 4.5.3.1.4).
    ///
    /// ESMTP extensions increase the MAIL FROM limit beyond the base
    /// 512 octets: RFC 1870 Section 4 (+26 for SIZE), RFC 6152
    /// Section 7 (+17 for BODY=), RFC 6531 Section 3.4 (+10 for
    /// SMTPUTF8), RFC 4865 Section 5 (+34 for HOLDFOR/HOLDUNTIL),
    /// and RFC 4954 Section 3 (+500 for AUTH=).
    pub(super) fn validate_mail_from_line_length(line_len: usize) -> Result<(), Error> {
        if line_len > Self::SMTP_MAX_MAIL_FROM_LINE {
            return Err(Error::Protocol(format!(
                "MAIL FROM command line exceeds {}-octet limit ({line_len} octets) \
                 (RFC 5321 Section 4.5.3.1.4 / RFC 1870 Section 4 / \
                 RFC 6152 Section 7 / RFC 6531 Section 3.4 / \
                 RFC 4865 Section 5 / RFC 4954 Section 3)",
                Self::SMTP_MAX_MAIL_FROM_LINE
            )));
        }
        Ok(())
    }

    /// Validate that a RCPT TO command line does not exceed the applicable
    /// line-length limit.
    ///
    /// RFC 5321 Section 4.5.3.1.4: base limit is 512 octets.
    /// RFC 3461 Section 5: when DSN parameters (NOTIFY, ORCPT) are present,
    /// the limit increases by 500 octets to 1012 octets.
    pub(super) fn validate_rcpt_to_line_length(
        line_len: usize,
        has_dsn_params: bool,
    ) -> Result<(), Error> {
        let limit = if has_dsn_params {
            Self::SMTP_MAX_RCPT_TO_DSN_LINE
        } else {
            Self::SMTP_MAX_COMMAND_LINE
        };
        if line_len > limit {
            return Err(Error::Protocol(format!(
                "RCPT TO command line exceeds {limit}-octet limit ({line_len} octets) \
                 (RFC 5321 Section 4.5.3.1.4{})",
                if has_dsn_params {
                    " / RFC 3461 Section 5"
                } else {
                    ""
                }
            )));
        }
        Ok(())
    }

    /// Validate that a recipient address is non-empty.
    ///
    /// RFC 5321 Section 4.1.1.3: `Forward-path = Path = "<" Mailbox ">"`.
    /// Validate sender and recipient addresses for a send operation.
    ///
    /// Shared by `send_with_params`, `send_bdat`, `send_lmtp`, and `send_lmtp_bdat`.
    /// Since the addresses are already validated by the [`ReversePath`] and
    /// [`ForwardPath`] constructors, this only checks that at least one
    /// recipient is present (RFC 5321 Section 3.3).
    ///
    /// RFC 5321 Section 3.3.
    pub(super) fn validate_send_addresses(
        _from: &ReversePath,
        recipients: &[ForwardPath],
    ) -> Result<(), Error> {
        // RFC 5321 Section 3.3: at least one RCPT TO is required.
        if recipients.is_empty() {
            return Err(Error::Protocol(
                "at least one recipient is required (RFC 5321 Section 3.3)".into(),
            ));
        }
        Ok(())
    }

    /// Validate that a string parameter does not contain CR or LF bytes
    /// that could cause SMTP command injection.
    ///
    /// RFC 5321 Section 4.1.2: SMTP command arguments follow the `mailbox`
    /// and `Domain` grammars, which prohibit bare CR and LF.
    pub(super) fn validate_no_crlf(value: &str, param_name: &str) -> Result<(), Error> {
        if value.bytes().any(|b| b == b'\r' || b == b'\n') {
            return Err(Error::Protocol(format!(
                "{param_name} must not contain CR or LF (RFC 5321 Section 4.1.2)"
            )));
        }
        Ok(())
    }

    /// Validate a general SMTP `String` argument as printable US-ASCII.
    ///
    /// RFC 5321 Sections 4.1.1.6-4.1.1.7 use `String` for VRFY/EXPN
    /// arguments. This helper enforces the transport-safety constraints:
    /// no ASCII control characters and no non-ASCII bytes.
    pub(super) fn validate_ascii_string(value: &str, param_name: &str) -> Result<(), Error> {
        for &b in value.as_bytes() {
            if b < 0x20 || b == 0x7F {
                return Err(Error::Protocol(format!(
                    "{param_name} contains control character (byte 0x{b:02X}); \
                     only printable US-ASCII is permitted \
                     (RFC 5321 Section 4.1.2)"
                )));
            }
            if b > 0x7F {
                return Err(Error::Protocol(format!(
                    "{param_name} contains non-ASCII characters; \
                     only printable US-ASCII is permitted \
                     (RFC 5321 Section 4.1.2)"
                )));
            }
        }
        Ok(())
    }

    /// Validate a VRFY/EXPN `String` argument when RFC 6531 `SMTPUTF8`
    /// is in use.
    ///
    /// RFC 6531 Section 3.7.4.2 allows non-ASCII UTF-8 in VRFY/EXPN
    /// arguments when the `SMTPUTF8` parameter is sent, but SMTP command
    /// arguments still must not contain ASCII control characters
    /// (RFC 5321 Section 4.1.2).
    pub(super) fn validate_utf8_string(value: &str, param_name: &str) -> Result<(), Error> {
        for &b in value.as_bytes() {
            if b < 0x20 || b == 0x7F {
                return Err(Error::Protocol(format!(
                    "{param_name} contains control character (byte 0x{b:02X}); \
                     SMTPUTF8 does not permit ASCII control characters in VRFY/EXPN arguments \
                     (RFC 5321 Section 4.1.2 / RFC 6531 Section 3.7.4.2)"
                )));
            }
        }
        Ok(())
    }

    /// Validate message data for the DATA path.
    ///
    /// Delegates to shared validators for NUL bytes, bare CR/LF, and
    /// line length. The DATA path adds CRLF before the terminating dot,
    /// so trailing-segment length includes +2 for the implicit CRLF.
    ///
    /// # Checks
    /// 1. **RFC 5321 Section 4.5.2** — no NUL bytes (0x00).
    /// 2. **RFC 5321 Section 2.3.8** — no bare CR or bare LF.
    /// 3. **RFC 5321 Section 4.5.3.1.6** — text lines ≤ 1000 octets
    ///    (including CRLF, not counting the transparency dot).
    pub(super) fn validate_data_message(data: &[u8]) -> Result<(), Error> {
        Self::validate_no_nul_bytes_in_data(data)?;
        Self::validate_no_bare_crlf(data)?;
        // DATA adds CRLF before the terminating dot (RFC 5321 Section
        // 4.1.1.4), so the trailing segment's effective length is +2.
        // RFC 5321 Section 4.5.3.1.6: the 1000-octet limit explicitly
        // excludes "the leading dot duplicated for transparency", so
        // dot-stuffing overhead is not counted against the limit.
        Self::validate_text_line_lengths(data, true)?;
        Ok(())
    }

    /// Validate that message data contains no NUL bytes (DATA path).
    ///
    /// RFC 5321 Section 4.5.2: "In the absence of a server-offered
    /// SMTP extension explicitly permitting it, a sending SMTP system
    /// MUST NOT send a message that contains octets with a value of
    /// 0x00."
    pub(super) fn validate_no_nul_bytes_in_data(data: &[u8]) -> Result<(), Error> {
        if data.contains(&0x00) {
            return Err(Error::Protocol(
                "message data contains NUL byte (0x00); \
                 SMTP DATA must not contain NUL octets \
                 (RFC 5321 Section 4.5.2)"
                    .into(),
            ));
        }
        Ok(())
    }

    /// Validate that message data uses CRLF line endings with no bare
    /// CR or bare LF.
    ///
    /// RFC 5321 Section 2.3.8: SMTP uses CRLF as the line ending; a
    /// bare CR (`\r` not followed by `\n`) or bare LF (`\n` not
    /// preceded by `\r`) violates the protocol and can cause
    /// interoperability failures.
    ///
    /// Shared by both the DATA and BDAT (without BINARYMIME) paths.
    /// RFC 3030 Section 3: "The CHUNKING service extension does not
    /// modify in any way the requirements for the content of the
    /// message."
    pub(super) fn validate_no_bare_crlf(data: &[u8]) -> Result<(), Error> {
        for i in 0..data.len() {
            if data[i] == b'\r' && data.get(i + 1) != Some(&b'\n') {
                return Err(Error::Protocol(
                    "message data contains bare CR (\\r not followed by \\n); \
                     SMTP requires CRLF line endings (RFC 5321 Section 2.3.8)"
                        .into(),
                ));
            }
            if data[i] == b'\n' && (i == 0 || data[i - 1] != b'\r') {
                return Err(Error::Protocol(
                    "message data contains bare LF (\\n not preceded by \\r); \
                     SMTP requires CRLF line endings (RFC 5321 Section 2.3.8)"
                        .into(),
                ));
            }
        }
        Ok(())
    }

    /// Validate that no text line exceeds 1000 octets (including CRLF).
    ///
    /// RFC 5321 Section 4.5.3.1.6: "The maximum total length of a text
    /// line including the `<CRLF>` is 1000 octets (not counting the
    /// leading dot duplicated for transparency)."
    ///
    /// `trailing_crlf_padding`: when `true`, the trailing segment
    /// (data not ending with CRLF) has +2 added to its effective
    /// length because the DATA path adds CRLF before the terminating
    /// dot (RFC 5321 Section 4.1.1.4). For BDAT, pass `false` since
    /// no implicit CRLF is appended.
    ///
    /// Shared by both the DATA and BDAT (without BINARYMIME) paths.
    pub(super) fn validate_text_line_lengths(
        data: &[u8],
        trailing_crlf_padding: bool,
    ) -> Result<(), Error> {
        let mut line_start: usize = 0;

        for i in 0..data.len() {
            // RFC 5321 Section 4.5.3.1.6: check line length at each CRLF.
            if data[i] == b'\n' && i > 0 && data[i - 1] == b'\r' {
                let line_len = i + 1 - line_start; // includes CRLF
                if line_len > Self::SMTP_MAX_TEXT_LINE {
                    return Err(Error::Protocol(format!(
                        "message text line exceeds {}-octet limit ({line_len} octets) \
                         (RFC 5321 Section 4.5.3.1.6)",
                        Self::SMTP_MAX_TEXT_LINE
                    )));
                }
                line_start = i + 1;
            }
        }

        // Check the trailing segment (data not ending with CRLF).
        let remaining = data.len() - line_start;
        if remaining > 0 {
            let effective_len = if trailing_crlf_padding {
                // DATA adds CRLF before the terminating dot.
                remaining + 2
            } else {
                remaining
            };
            if effective_len > Self::SMTP_MAX_TEXT_LINE {
                return Err(Error::Protocol(format!(
                    "message text line exceeds {}-octet limit ({effective_len} octets) \
                     (RFC 5321 Section 4.5.3.1.6)",
                    Self::SMTP_MAX_TEXT_LINE
                )));
            }
        }

        Ok(())
    }

    /// RFC 5321 Section 4.5.3.1.6: "The maximum total length of a text
    /// line including the `<CRLF>` is 1000 octets (not counting the
    /// leading dot duplicated for transparency)."
    pub(super) const SMTP_MAX_TEXT_LINE: usize = 1000;

    /// Compute the message size for the RFC 1870 SIZE parameter.
    ///
    /// RFC 1870 Section 5: "The message size is defined as the number
    /// of octets, including CR-LF pairs, but not the SMTP DATA
    /// command's terminating dot or doubled quoting dots."
    /// The SIZE parameter uses the raw message size — dot-stuffing
    /// overhead is SMTP transfer encoding and is excluded.
    ///
    /// RFC 1870 Section 3: SIZE includes "the terminating CRLF of the
    /// last line." When the message does not already end with CRLF, the
    /// sender adds one before the terminating dot (RFC 5321 Section
    /// 4.1.1.4), and this implicit CRLF must be counted.
    pub(super) fn data_message_size(message: &[u8]) -> usize {
        // RFC 1870 Section 5: "The message size is defined as the number
        // of octets, including CR-LF pairs, but not the SMTP DATA
        // command's terminating dot or doubled quoting dots."
        // The SIZE parameter uses the raw message size — dot-stuffing
        // overhead is SMTP transfer encoding and is excluded.
        if message.ends_with(b"\r\n") {
            message.len()
        } else {
            // RFC 1870 Section 3 / RFC 5321 Section 4.1.1.4: the DATA
            // path adds an implicit CRLF before the terminating dot when
            // the message does not already end with CRLF. This implicit
            // CRLF terminates the last line of the message and is part
            // of the message content, so it is included in the size.
            message.len() + 2
        }
    }

    /// Send the MAIL FROM command to the server and check for success.
    ///
    /// RFC 5321 Section 4.1.1.2: Encodes the command with optional ESMTP
    /// parameters, validates command-line length (Section 4.5.3.1.4),
    /// sends it, and verifies the server's response.
    pub(super) async fn send_mail_from(
        inner: &mut SmtpInner,
        from: &ReversePath,
        message: &[u8],
        message_size: usize,
        params: Option<&crate::types::MailFromParams>,
    ) -> Result<(), Error> {
        let mut buf = BytesMut::new();
        let is_8bit = Self::message_contains_8bit(message);
        Self::encode_mail_from_cmd(
            &inner.capabilities,
            &mut buf,
            from,
            message_size,
            params,
            is_8bit,
        )?;
        // RFC 5321 Section 4.5.3.1.4 / RFC 1870 Section 4 / RFC 6152
        // Section 7 / RFC 6531 Section 3.4: MAIL FROM has an extended
        // command line limit to accommodate ESMTP parameters.
        Self::validate_mail_from_line_length(buf.len())?;
        inner.write_all(&buf).await?;
        let resp = inner.read_response().await?;
        if !resp.is_success() {
            return Err(Self::response_to_error(resp));
        }
        Ok(())
    }

    /// Send RCPT TO for each recipient and collect results.
    ///
    /// RFC 5321 Section 4.1.1.3: sends a RCPT TO command for each recipient,
    /// tracking which were accepted and which were rejected. If all recipients
    /// are rejected, resets the transaction (RSET) and returns
    /// [`Error::AllRecipientsFailed`].
    ///
    /// When `rcpt_params` is `Some`, each recipient is paired by index with
    /// its corresponding [`RcptToParams`] and encoded via
    /// [`encode_rcpt_to_full`](crate::codec::encode::encode_rcpt_to_full)
    /// to include DSN parameters (NOTIFY, ORCPT per RFC 3461 Sections 4.1–4.2).
    /// When `None`, the plain [`encode_rcpt_to`](crate::codec::encode::encode_rcpt_to)
    /// is used.
    ///
    /// Returns the list of accepted recipient addresses and the list of
    /// rejected recipients with their server responses (RFC 5321 Section 3.3).
    pub(super) async fn send_rcpt_to_batch(
        inner: &mut SmtpInner,
        recipients: &[ForwardPath],
        rcpt_params: Option<&[crate::types::RcptToParams]>,
    ) -> Result<(Vec<ForwardPath>, Vec<crate::types::RejectedRecipient>), Error> {
        let mut buf = BytesMut::new();
        let mut accepted = Vec::new();
        let mut rejected = Vec::new();
        for (i, fp) in recipients.iter().enumerate() {
            buf.clear();
            if let Some(params) = rcpt_params {
                // RFC 3461 Sections 4.1–4.2: encode with DSN parameters.
                encode::encode_rcpt_to_full(&mut buf, fp, &params[i])?;
            } else {
                encode::encode_rcpt_to(&mut buf, fp)?;
            }
            // RFC 5321 Section 4.5.3.1.4 / RFC 3461 Section 5: validate
            // command line length, using the extended 1012-octet limit when
            // DSN parameters are present for this recipient.
            let has_dsn = rcpt_params.is_some_and(|rp| !rp[i].is_empty());
            Self::validate_rcpt_to_line_length(buf.len(), has_dsn)?;
            inner.write_all(&buf).await?;
            let resp = inner.read_response().await?;
            if resp.is_success() {
                accepted.push(fp.clone());
            } else {
                tracing::debug!(
                    recipient = fp.as_str(),
                    code = resp.code,
                    "RCPT TO rejected"
                );
                rejected.push(crate::types::RejectedRecipient {
                    recipient: fp.clone(),
                    response: resp,
                });
            }
        }

        if accepted.is_empty() {
            // RFC 5321 Section 3.3: abort the mail transaction opened by
            // MAIL FROM so the connection is left in a clean state.
            inner.rset_best_effort().await;
            return Err(Error::AllRecipientsFailed {
                count: recipients.len(),
                // Extract just the responses for the error variant.
                responses: rejected.into_iter().map(|r| r.response).collect(),
            });
        }

        Ok((accepted, rejected))
    }

    /// Validate all prerequisites for the DATA send path and return message size
    /// (RFC 5321 Section 3.3, RFC 3030 Section 2, RFC 1870 Section 3).
    ///
    /// Shared by `send_with_params` and `send_lmtp`. Checks:
    /// - BODY=BINARYMIME is rejected (incompatible with DATA, RFC 3030 Section 2)
    /// - ESMTP params are valid for server capabilities (RFC 5321 Section 2.2.1)
    /// - Message size within server limit (RFC 1870 Sections 3–4)
    /// - DATA message format: CRLF line endings, line length (RFC 5321 Section 2.3.8)
    /// - 7-bit content when required (RFC 1652 Section 1 / RFC 6152 Section 3)
    pub(super) fn validate_data_prerequisites(
        capabilities: &ServerCapabilities,
        message: &[u8],
        params: Option<&crate::types::MailFromParams>,
        is_tls: bool,
    ) -> Result<usize, Error> {
        // RFC 3030 Section 2: "BINARYMIME cannot be used with the DATA
        // command." The DATA path applies dot-stuffing which corrupts
        // binary content.
        if let Some(p) = params {
            if p.body == Some(crate::types::BodyType::BinaryMime) {
                return Err(Error::Protocol(
                    "BODY=BINARYMIME cannot be used with DATA; use BDAT/CHUNKING \
                     instead (RFC 3030 Section 2)"
                        .into(),
                ));
            }
        }
        // RFC 5321 Section 2.2.1: validate ESMTP params against capabilities.
        Self::validate_params(capabilities, params, is_tls)?;
        // RFC 1870 Section 3: SIZE uses the original message size (excluding
        // dot-stuffing overhead, which is protocol overhead per RFC 5321 Section 4.5.2).
        let message_size = Self::data_message_size(message);
        // RFC 1870 Section 4: check message size against server limit.
        Self::check_size_limit(capabilities, message_size)?;
        // RFC 5321 Section 2.3.8: DATA requires CRLF line endings.
        Self::validate_data_message(message)?;
        // RFC 1652 Section 1 / RFC 5321 Section 2.3.1: without 8BITMIME,
        // SMTP is limited to 7-bit content.
        // RFC 6152 Section 3: BODY=7BIT declares content is all 7-bit;
        // enforce this regardless of server capabilities.
        if Self::is_body_declared_7bit(params) || !capabilities.supports_8bitmime() {
            Self::validate_7bit_content(message)?;
        }
        Ok(message_size)
    }

    /// Validate all prerequisites for the BDAT send path
    /// (RFC 3030 Section 3, RFC 1870 Section 4).
    ///
    /// Shared by `send_bdat` and `send_lmtp_bdat`. Checks:
    /// - CHUNKING extension is available (RFC 3030 Section 3)
    /// - ESMTP params are valid for server capabilities (RFC 5321 Section 2.2.1)
    /// - Message size within server limit (RFC 1870 Section 4)
    /// - NUL byte and 7-bit content restrictions (RFC 5321 Section 4.5.2)
    pub(super) fn validate_bdat_prerequisites(
        capabilities: &ServerCapabilities,
        message: &[u8],
        params: Option<&crate::types::MailFromParams>,
        is_tls: bool,
    ) -> Result<(), Error> {
        // RFC 3030 Section 3: CHUNKING extension required.
        if !capabilities.supports_chunking() {
            return Err(Error::Protocol(
                "server does not support CHUNKING (RFC 3030)".into(),
            ));
        }
        // RFC 5321 Section 2.2.1: validate ESMTP params against capabilities.
        // Note: BODY=BINARYMIME is valid with BDAT (RFC 3030 Section 2).
        Self::validate_params(capabilities, params, is_tls)?;
        // RFC 1870 Section 4: check message size against server limit.
        Self::check_size_limit(capabilities, message.len())?;
        // BDAT does not require CRLF line endings or enforce line length limits
        // (RFC 3030 Section 3). However, NUL and 7-bit content restrictions
        // still apply without BINARYMIME/8BITMIME.
        Self::validate_bdat_content(capabilities, message, params)?;
        Ok(())
    }

    /// Validate message content for BDAT/CHUNKING paths.
    ///
    /// RFC 3030 Section 3: "The CHUNKING service extension does not
    /// modify in any way the requirements for the content of the
    /// message." Without BINARYMIME, all standard SMTP content
    /// requirements apply:
    ///
    /// - **RFC 5321 Section 4.5.2** — no NUL bytes.
    /// - **RFC 5321 Section 2.3.8** — no bare CR or bare LF.
    /// - **RFC 5321 Section 4.5.3.1.6** — text lines ≤ 1000 octets
    ///   (including CRLF).
    /// - **RFC 1652 Section 1** — 7-bit content unless 8BITMIME.
    /// - **RFC 6152 Section 3** — BODY=7BIT forces 7-bit.
    ///
    /// RFC 3030 Section 4 allows arbitrary octets for BINARYMIME payloads,
    /// but RFC 3030 Section 2 still requires canonical CRLF line endings for
    /// top-level `text/*` MIME entities.
    pub(super) fn validate_bdat_content(
        capabilities: &ServerCapabilities,
        message: &[u8],
        params: Option<&crate::types::MailFromParams>,
    ) -> Result<(), Error> {
        let is_binary = params.is_some_and(|p| p.body == Some(crate::types::BodyType::BinaryMime));
        if is_binary {
            // RFC 3030 Section 2: a BINARYMIME message is still expected to be
            // canonical MIME. In particular, top-level text/* content MUST use
            // CRLF line endings even though non-text bodies may carry arbitrary
            // octets.
            if Self::binarymime_requires_canonical_text_lines(message) {
                Self::validate_no_bare_crlf(message)?;
            }
            return Ok(());
        }

        Self::validate_no_nul_bytes(message)?;
        // RFC 3030 Section 3: content requirements are unchanged
        // without BINARYMIME — enforce CRLF and line length.
        Self::validate_no_bare_crlf(message)?;
        // BDAT does not append CRLF before a terminator (no dot
        // terminator), so trailing_crlf_padding is false.
        Self::validate_text_line_lengths(message, false)?;
        if Self::is_body_declared_7bit(params) || !capabilities.supports_8bitmime() {
            Self::validate_7bit_content(message)?;
        }
        Ok(())
    }

    /// Returns `true` when a BINARYMIME payload still needs canonical line
    /// validation because its top-level MIME type contains line-oriented
    /// message syntax.
    ///
    /// RFC 3030 Section 2 says the MIME message itself must be properly
    /// formed and specifically calls out `text/*` as requiring
    /// CRLF-terminated lines. The same canonical requirement applies to the
    /// textual structure of `multipart/*` and `message/*` entities, which
    /// carry MIME boundaries, nested headers, and other RFC 5322-style line
    /// syntax. When `Content-Type` is missing or malformed, MIME defaults to
    /// `text/plain` (RFC 2045 Section 5.2), so the conservative choice is to
    /// keep canonical line validation enabled.
    pub(super) fn binarymime_requires_canonical_text_lines(message: &[u8]) -> bool {
        match Self::top_level_mime_type(message) {
            Some(mime_type) => {
                mime_type.starts_with("text/")
                    || mime_type.starts_with("multipart/")
                    || mime_type.starts_with("message/")
            }
            None => true,
        }
    }

    /// Extract the top-level MIME media type from the RFC 5322 header block.
    ///
    /// Returns the normalized `type/subtype` token without parameters, or
    /// `None` when no usable `Content-Type` field is present.
    ///
    /// RFC 2045 Section 5.1 defines `Content-Type`; RFC 2045 Section 5.2
    /// defaults a missing field to `text/plain`.
    pub(super) fn top_level_mime_type(message: &[u8]) -> Option<String> {
        let header_len = Self::header_block_len(message);
        if header_len == 0 {
            return None;
        }

        let content_type = Self::header_field_value(&message[..header_len], "content-type")?;
        let raw_type = content_type
            .split(';')
            .next()
            .unwrap_or_default()
            .trim()
            .to_ascii_lowercase();
        let slash = raw_type.find('/')?;
        let type_part = raw_type[..slash].trim();
        let subtype_part = raw_type[slash + 1..].trim();
        if type_part.is_empty() || subtype_part.is_empty() {
            return None;
        }
        Some(format!("{type_part}/{subtype_part}"))
    }

    /// Extract a case-insensitive RFC 5322 header field value from a header block.
    ///
    /// Continuation lines are unfolded by joining them with a single space
    /// (RFC 5322 Section 2.2.3).
    pub(super) fn header_field_value(header_block: &[u8], target_name: &str) -> Option<String> {
        let mut current_name: Option<String> = None;
        let mut current_value = String::new();

        for raw_line in header_block.split(|&byte| byte == b'\n') {
            let line = raw_line.strip_suffix(b"\r").unwrap_or(raw_line);
            if line.is_empty() {
                break;
            }

            if matches!(line.first(), Some(b' ' | b'\t')) {
                if current_name.as_deref() == Some(target_name) {
                    if !current_value.is_empty() {
                        current_value.push(' ');
                    }
                    current_value.push_str(String::from_utf8_lossy(line).trim());
                }
                continue;
            }

            if current_name.as_deref() == Some(target_name) {
                return Some(current_value);
            }

            let colon = line.iter().position(|&byte| byte == b':')?;
            current_name = Some(String::from_utf8_lossy(&line[..colon]).to_ascii_lowercase());
            current_value.clear();
            current_value.push_str(String::from_utf8_lossy(&line[colon + 1..]).trim());
        }

        (current_name.as_deref() == Some(target_name)).then_some(current_value)
    }

    /// Check if MAIL FROM params declare BODY=7BIT.
    ///
    /// RFC 6152 Section 3: BODY=7BIT declares content is all 7-bit;
    /// the library must enforce this regardless of server capabilities.
    pub(super) fn is_body_declared_7bit(params: Option<&crate::types::MailFromParams>) -> bool {
        params.is_some_and(|p| p.body == Some(crate::types::BodyType::SevenBit))
    }

    /// Validate that message data does not contain NUL bytes.
    ///
    /// RFC 5321 Section 4.5.2: "In the absence of a server-offered SMTP
    /// extension explicitly permitting it, a sending SMTP system MUST NOT
    /// send a message that contains octets with a value of 0x00."
    ///
    /// The BINARYMIME extension (RFC 3030 Section 4) permits NUL bytes;
    /// CHUNKING alone does not.
    pub(super) fn validate_no_nul_bytes(data: &[u8]) -> Result<(), Error> {
        if data.contains(&0x00) {
            return Err(Error::Protocol(
                "message data contains NUL byte (0x00); \
                 SMTP MUST NOT send NUL octets without BINARYMIME \
                 (RFC 5321 Section 4.5.2 / RFC 3030 Section 4)"
                    .into(),
            ));
        }
        Ok(())
    }

    /// Validate that message data contains only 7-bit content.
    ///
    /// RFC 1652 Section 1: "In the absence of [the 8BITMIME] extension,
    /// an SMTP client MUST NOT transmit 8-bit data in the mail body."
    ///
    /// RFC 5321 Section 2.3.1: without 8BITMIME, SMTP is limited to the
    /// transmission of 7-bit US-ASCII content.
    ///
    /// This check applies on non-BINARYMIME send paths whenever the server
    /// does NOT advertise 8BITMIME.
    pub(super) fn validate_7bit_content(data: &[u8]) -> Result<(), Error> {
        for &b in data {
            if b > 0x7F {
                return Err(Error::Protocol(
                    "message contains 8-bit content (bytes > 0x7F) but the server \
                     does not advertise 8BITMIME; use BODY=8BITMIME with a server \
                     that supports it, or encode the message as 7-bit \
                     (RFC 1652 Section 1 / RFC 5321 Section 2.3.1)"
                        .into(),
                ));
            }
        }
        Ok(())
    }

    /// Encode a MAIL FROM command into `buf`, merging caller-supplied
    /// [`MailFromParams`] with the SIZE parameter derived from the server's
    /// advertised capabilities (RFC 1870 Section 3).
    ///
    /// When `params` is `None`, the basic `MAIL FROM:<addr>` form is used
    /// with an optional SIZE parameter. When `params` is `Some`, the
    /// extended form is used, including BODY= (RFC 1652) and SMTPUTF8
    /// (RFC 6531) parameters if set by the caller.
    ///
    /// RFC 6152 Section 3: when the message contains 8-bit data
    /// (`message_is_8bit` is true) and the server supports 8BITMIME,
    /// `BODY=8BITMIME` is automatically included in MAIL FROM — even
    /// when the caller did not supply explicit [`MailFromParams`].
    pub(super) fn encode_mail_from_cmd(
        capabilities: &ServerCapabilities,
        buf: &mut BytesMut,
        from: &ReversePath,
        message_len: usize,
        params: Option<&crate::types::MailFromParams>,
        message_is_8bit: bool,
    ) -> Result<(), Error> {
        if let Some(p) = params {
            // Merge caller params with auto-SIZE.
            let mut merged = p.clone();
            if capabilities.supports_size() && merged.size.is_none() {
                merged.size = Some(message_len as u64);
            }
            // RFC 6531 Section 3.4: "If the SMTPUTF8 MAIL FROM parameter
            // is used, the BODY parameter (RFC 6152) MUST also be used,
            // with a value of '8BITMIME'." Auto-add BODY=8BITMIME when
            // SMTPUTF8 is set and the caller hasn't set a BODY parameter.
            //
            // RFC 6152 Section 3: also auto-declare BODY=8BITMIME when
            // the message contains 8-bit content and the server advertises
            // 8BITMIME.
            if merged.body.is_none()
                && (merged.smtputf8 || (message_is_8bit && capabilities.supports_8bitmime()))
            {
                merged.body = Some(crate::types::BodyType::EightBitMime);
            }
            // RFC 5321 Section 4.5.2: 7-bit is the default encoding.
            // Silently omit the redundant BODY=7BIT parameter when the
            // server does not advertise 8BITMIME or BINARYMIME, since
            // the BODY keyword is an ESMTP extension (RFC 6152 Section 3).
            if merged.body == Some(crate::types::BodyType::SevenBit)
                && !capabilities.supports_8bit_or_binary()
            {
                merged.body = None;
            }
            encode::encode_mail_from_full(buf, from, &merged)?;
        } else if message_is_8bit && capabilities.supports_8bitmime() {
            // RFC 6152 Section 3: "When a client SMTP transmits a message
            // body consisting of 8bit data to a server SMTP, it must also
            // transmit a BODY=8BITMIME parameter on the MAIL FROM command."
            let auto_params = crate::types::MailFromParams {
                size: if capabilities.supports_size() {
                    Some(message_len as u64)
                } else {
                    None
                },
                body: Some(crate::types::BodyType::EightBitMime),
                smtputf8: false,
                ..Default::default()
            };
            encode::encode_mail_from_full(buf, from, &auto_params)?;
        } else {
            let size = if capabilities.supports_size() {
                Some(message_len as u64)
            } else {
                None
            };
            encode::encode_mail_from(buf, from, size)?;
        }
        Ok(())
    }

    /// Check whether message data contains any 8-bit octets (bytes > 0x7F).
    ///
    /// Used to auto-detect 8-bit content for the BODY=8BITMIME declaration
    /// per RFC 6152 Section 3.
    pub(super) fn message_contains_8bit(data: &[u8]) -> bool {
        data.iter().any(|&b| b > 0x7F)
    }

    /// Check whether the RFC 5322 header block contains UTF-8 octets that
    /// require the SMTPUTF8 extension.
    ///
    /// RFC 6531 Section 3.1 item 4 requires the SMTPUTF8 MAIL FROM parameter
    /// when the message being sent is internationalized. RFC 6532 Sections 3.2
    /// and 3.6 permit UTF-8 directly in header fields, so any non-ASCII octet
    /// before the blank-line header/body separator means the message needs
    /// SMTPUTF8 support.
    pub(super) fn message_headers_require_smtputf8(data: &[u8]) -> bool {
        let header_end = Self::header_block_len(data);
        data[..header_end].iter().any(|&b| b > 0x7F)
    }

    /// Determine the length of the leading RFC 5322 header block, if present.
    ///
    /// RFC 5322 Section 2.2: header fields are a sequence of field-name lines
    /// optionally followed by folded continuation lines. Raw BDAT payloads and
    /// malformed messages may omit headers entirely; in those cases this
    /// returns 0 so body octets are not mistaken for header data.
    pub(super) fn header_block_len(data: &[u8]) -> usize {
        let mut offset = 0usize;
        let mut saw_header = false;
        let mut saw_complete_line = false;

        while offset < data.len() {
            let line_end = data[offset..]
                .iter()
                .position(|&byte| byte == b'\n')
                .map_or(data.len(), |idx| offset + idx);
            let line = if line_end > offset && data[line_end.saturating_sub(1)] == b'\r' {
                &data[offset..line_end - 1]
            } else {
                &data[offset..line_end]
            };

            if line.is_empty() {
                return if saw_header { offset } else { 0 };
            }

            let is_continuation = matches!(line.first(), Some(b' ' | b'\t'));
            if is_continuation {
                if !saw_header {
                    return 0;
                }
            } else if Self::looks_like_header_field_line(line) {
                saw_header = true;
            } else {
                return if saw_header { offset } else { 0 };
            }

            if line_end == data.len() {
                // RFC 5322 Section 2.2 models header fields as lines. If the
                // entire payload is a single unterminated header-looking line,
                // treat it conservatively as body data so raw payloads such as
                // `Note: café` are not reclassified as SMTPUTF8 headers.
                return if saw_header && saw_complete_line {
                    data.len()
                } else {
                    0
                };
            }
            saw_complete_line = true;
            offset = line_end + 1;
        }

        if saw_header {
            data.len()
        } else {
            0
        }
    }

    /// Check whether a line begins with a syntactically valid RFC 5322 field name.
    ///
    /// RFC 5322 Section 3.6: `field = field-name ":" unstructured`.
    /// RFC 5322 Section 3.6.8: `field-name = 1*ftext`.
    pub(super) fn looks_like_header_field_line(line: &[u8]) -> bool {
        let Some(colon_idx) = line.iter().position(|&byte| byte == b':') else {
            return false;
        };
        colon_idx > 0
            && line[..colon_idx]
                .iter()
                .all(|&byte| (33..=57).contains(&byte) || (59..=126).contains(&byte))
    }

    /// Check whether a send operation requires the SMTPUTF8 extension.
    ///
    /// RFC 6531 Section 3.1 item 4 requires SMTPUTF8 when the message being
    /// sent is internationalized. RFC 6531 Section 3.3 extends SMTP mailbox
    /// syntax to UTF-8 for MAIL FROM and RCPT TO only when SMTPUTF8 is active.
    pub(super) fn send_requires_smtputf8(
        from: &ReversePath,
        recipients: &[ForwardPath],
        message: &[u8],
    ) -> bool {
        from.requires_smtputf8()
            || recipients.iter().any(ForwardPath::requires_smtputf8)
            || Self::message_headers_require_smtputf8(message)
    }

    /// Merge caller-supplied MAIL FROM parameters with SMTPUTF8 inferred
    /// from the envelope and raw message.
    ///
    /// RFC 6531 Section 3.1 item 4: SMTPUTF8 is required for
    /// internationalized messages.
    /// RFC 6531 Section 3.3: non-ASCII envelope addresses require SMTPUTF8.
    /// RFC 6531 Section 3.4: the MAIL FROM parameter must be present when
    /// SMTPUTF8 is required and supported.
    pub(super) fn effective_mail_from_params(
        capabilities: &ServerCapabilities,
        from: &ReversePath,
        recipients: &[ForwardPath],
        message: &[u8],
        params: Option<&crate::types::MailFromParams>,
    ) -> Result<crate::types::MailFromParams, Error> {
        let mut effective = params.cloned().unwrap_or_default();
        if Self::send_requires_smtputf8(from, recipients, message) {
            if !capabilities.supports_smtputf8() {
                return Err(Error::SmtpUtf8Required);
            }
            effective.smtputf8 = true;
        }
        Ok(effective)
    }

    /// Check message size against the server's advertised SIZE limit.
    ///
    /// RFC 1870 Section 4: the client SHOULD NOT send a message larger
    /// than the server's declared fixed maximum message size.
    pub(super) fn check_size_limit(
        capabilities: &ServerCapabilities,
        message_len: usize,
    ) -> Result<(), Error> {
        if let Some(limit) = capabilities.size_limit() {
            if message_len as u64 > limit {
                return Err(Error::Protocol(format!(
                    "message size ({message_len} bytes) exceeds server SIZE limit \
                     ({limit} bytes) (RFC 1870 Section 4)"
                )));
            }
        }
        Ok(())
    }

    /// Validate that the server advertises support for each ESMTP
    /// extension the caller is requesting via [`MailFromParams`].
    ///
    /// RFC 5321 Section 2.2.1: "An SMTP client MUST NOT use SMTP
    /// service extensions that have not been offered by the server."
    pub(super) fn validate_params(
        capabilities: &ServerCapabilities,
        params: Option<&crate::types::MailFromParams>,
        is_tls: bool,
    ) -> Result<(), Error> {
        let Some(p) = params else { return Ok(()) };
        Self::validate_extension_caps(capabilities, p, is_tls)?;
        Self::validate_smtputf8_body(p)?;
        Self::validate_body_type(capabilities, p)
    }

    /// RFC 5321 Section 2.2.1: "An SMTP client MUST NOT use SMTP service
    /// extensions that have not been offered by the server."
    #[allow(clippy::too_many_lines)]
    pub(super) fn validate_extension_caps(
        capabilities: &ServerCapabilities,
        p: &crate::types::MailFromParams,
        is_tls: bool,
    ) -> Result<(), Error> {
        if p.size.is_some() && !capabilities.supports_size() {
            return Err(Error::Protocol(
                "SIZE parameter requires server SIZE support \
                 (RFC 1870 Section 3 / RFC 5321 Section 2.2.1)"
                    .into(),
            ));
        }
        if p.smtputf8 && !capabilities.supports_smtputf8() {
            return Err(Error::Protocol(
                "SMTPUTF8 parameter requires server SMTPUTF8 support \
                 (RFC 6531 Section 3.4)"
                    .into(),
            ));
        }
        if p.smtputf8 && !capabilities.supports_8bitmime() {
            return Err(Error::Protocol(
                "SMTPUTF8 requires server 8BITMIME support; \
                 the server advertises SMTPUTF8 but not 8BITMIME \
                 (RFC 6531 Section 3.4 / Section 3.2)"
                    .into(),
            ));
        }
        if p.requiretls && !capabilities.supports_requiretls() {
            return Err(Error::Protocol(
                "REQUIRETLS parameter requires server REQUIRETLS support \
                 (RFC 8689 Section 3 / RFC 5321 Section 2.2.1)"
                    .into(),
            ));
        }
        // RFC 8689 Section 3: "the SMTP session used to send a given
        // message MUST itself be TLS-protected."
        if p.requiretls && !is_tls {
            return Err(Error::Protocol(
                "REQUIRETLS requires a TLS-protected session; \
                 the current connection is not encrypted \
                 (RFC 8689 Section 3)"
                    .into(),
            ));
        }
        if (p.ret.is_some() || p.envid.is_some()) && !capabilities.supports_dsn() {
            return Err(Error::Protocol(
                "DSN parameters (RET/ENVID) require server DSN support \
                 (RFC 3461 Section 4 / RFC 5321 Section 2.2.1)"
                    .into(),
            ));
        }
        if p.auth.is_some() && !capabilities.supports_auth_extension() {
            return Err(Error::Protocol(
                "AUTH parameter requires server AUTH support \
                 (RFC 4954 Section 5 / RFC 5321 Section 2.2.1)"
                    .into(),
            ));
        }
        // SmtpAuthParam::Mailbox contains a validated Mailbox newtype that
        // cannot be empty by construction (RFC 5321 Section 4.1.2).
        if (p.hold_for.is_some() || p.hold_until.is_some())
            && !capabilities.supports_future_release()
        {
            return Err(Error::Protocol(
                "HOLDFOR/HOLDUNTIL parameters require server FUTURERELEASE support \
                 (RFC 4865 Section 5 / RFC 5321 Section 2.2.1)"
                    .into(),
            ));
        }
        // RFC 4865 Section 5: HOLDFOR and HOLDUNTIL are mutually exclusive.
        // A MAIL FROM command MUST contain at most one of these parameters.
        if p.hold_for.is_some() && p.hold_until.is_some() {
            return Err(Error::Protocol(
                "HOLDFOR and HOLDUNTIL are mutually exclusive; \
                 only one may be specified per MAIL FROM command \
                 (RFC 4865 Section 5)"
                    .into(),
            ));
        }
        // RFC 4865 Section 4: "the value MUST be less than or equal to the
        // [server-advertised] maximum hold interval."
        if let Some(hold_for) = p.hold_for {
            validate_hold_for_seconds(hold_for)?;
            if let Some(max_interval) = capabilities.future_release_max_interval() {
                if hold_for > max_interval {
                    return Err(Error::Protocol(format!(
                        "HOLDFOR value {hold_for}s exceeds server maximum \
                         {max_interval}s (RFC 4865 Section 4)"
                    )));
                }
            }
        }
        // RFC 4865 Section 4: "the client MUST NOT set a hold-until time
        // that is later than the [server-advertised] max-datetime."
        // Both values are RFC 3339 datetime strings.  We parse them to
        // UTC epoch seconds for correct chronological comparison across
        // timezone offsets.
        if let Some(ref hold_until) = p.hold_until {
            validate_hold_until_datetime(hold_until)?;
            if let Some(max_datetime) = capabilities.future_release_max_datetime() {
                let hold_key = parse_rfc3339_to_utc_key(hold_until).ok_or_else(|| {
                    Error::Protocol(format!(
                        "HOLDUNTIL must be a valid RFC 3339 date-time: {hold_until} \
                         (RFC 4865 Section 5 / RFC 3339 Section 5.6)"
                    ))
                })?;
                let exceeds = match parse_rfc3339_to_utc_key(max_datetime) {
                    Some(max_key) => hold_key > max_key,
                    // Postel's law: if the server advertises a malformed
                    // max-datetime, ignore that malformed bound rather than
                    // reject a valid client parameter.
                    None => false,
                };
                if exceeds {
                    return Err(Error::Protocol(format!(
                        "HOLDUNTIL value {hold_until} exceeds server maximum \
                         {max_datetime} (RFC 4865 Section 4)"
                    )));
                }
            }
        }
        if p.deliver_by.is_some() && !capabilities.supports_deliver_by() {
            return Err(Error::Protocol(
                "BY parameter requires server DELIVERBY support \
                 (RFC 2852 Section 3 / RFC 5321 Section 2.2.1)"
                    .into(),
            ));
        }
        // RFC 2852 Section 2: the EHLO DELIVERBY parameter is the minimum
        // deliver-by time the server will accept for by-mode Return.
        if let Some(ref db) = p.deliver_by {
            validate_deliver_by_value(db)?;
            if db.mode == crate::types::DeliverByMode::Return && db.seconds > 0 {
                if let Some(min_secs) = capabilities.deliver_by_min() {
                    #[allow(clippy::cast_sign_loss)]
                    let secs = db.seconds as u64;
                    if secs < min_secs {
                        return Err(Error::Protocol(format!(
                            "DELIVERBY value {}s is below server minimum \
                             {min_secs}s (RFC 2852 Section 2)",
                            db.seconds
                        )));
                    }
                }
            }
        }
        Self::validate_future_release_deliver_by_relation(p)?;
        if p.mt_priority.is_some() && !capabilities.supports_mt_priority() {
            return Err(Error::Protocol(
                "MT-PRIORITY parameter requires server MT-PRIORITY support \
                 (RFC 6758 Section 4 / RFC 5321 Section 2.2.1)"
                    .into(),
            ));
        }
        // RFC 6758 Section 4: priority values range from -9 to 9 (the full
        // STANAG 4406 range).  Values outside this range are invalid.
        if let Some(v) = p.mt_priority {
            if !(-9..=9).contains(&v) {
                return Err(Error::Protocol(format!(
                    "MT-PRIORITY value {v} is outside the valid range -9..=9 \
                     (RFC 6758 Section 4)"
                )));
            }
        }
        Ok(())
    }

    /// RFC 4865 Section 5.2.1: the future release time MAY NOT be farther
    /// in the future than the DELIVERBY deadline.
    pub(super) fn validate_future_release_deliver_by_relation(
        p: &crate::types::MailFromParams,
    ) -> Result<(), Error> {
        let Some(deliver_by) = p.deliver_by else {
            return Ok(());
        };

        if let Some(hold_for) = p.hold_for {
            match u64::try_from(deliver_by.seconds) {
                Ok(by_seconds) if hold_for <= by_seconds => {}
                _ => {
                    return Err(Error::Protocol(format!(
                        "HOLDFOR value {hold_for}s exceeds DELIVERBY deadline {}s \
                         (RFC 4865 Section 5.2.1)",
                        deliver_by.seconds
                    )));
                }
            }
        }

        if let Some(ref hold_until) = p.hold_until {
            let hold_key = parse_rfc3339_to_utc_key(hold_until).ok_or_else(|| {
                Error::Protocol(format!(
                    "HOLDUNTIL must be a valid RFC 3339 date-time: {hold_until} \
                     (RFC 4865 Section 5 / RFC 3339 Section 5.6)"
                ))
            })?;
            let now = SystemTime::now().duration_since(UNIX_EPOCH).map_err(|_| {
                Error::Protocol(
                    "system clock is before the Unix epoch; cannot validate HOLDUNTIL against DELIVERBY \
                     (RFC 4865 Section 5.2.1)"
                        .into(),
                )
            })?;
            let now_secs = i64::try_from(now.as_secs()).map_err(|_| {
                Error::Protocol(
                    "system clock exceeds supported range for DELIVERBY comparison \
                     (RFC 4865 Section 5.2.1)"
                        .into(),
                )
            })?;
            let deadline_secs = now_secs.checked_add(deliver_by.seconds).ok_or_else(|| {
                Error::Protocol(
                    "DELIVERBY deadline overflow during FUTURERELEASE validation \
                     (RFC 4865 Section 5.2.1)"
                        .into(),
                )
            })?;
            let deadline_key = (deadline_secs, now.subsec_nanos());
            if hold_key > deadline_key {
                return Err(Error::Protocol(format!(
                    "HOLDUNTIL value {hold_until} exceeds DELIVERBY deadline {}s \
                     (RFC 4865 Section 5.2.1)",
                    deliver_by.seconds
                )));
            }
        }

        Ok(())
    }

    /// RFC 6531 Section 3.6: SMTPUTF8 requires 8-bit-capable BODY type.
    ///
    /// BODY=7BIT is incompatible with SMTPUTF8 because internationalized
    /// headers contain non-ASCII octets. Both BODY=8BITMIME (RFC 6152)
    /// and BODY=BINARYMIME (RFC 3030) are valid:
    ///
    /// > The SMTPUTF8 extension MAY be used as follows:
    /// > - with the BODY=8BITMIME parameter [RFC6152], or
    /// > - with the BODY=BINARYMIME parameter, if the SMTP server
    /// >   advertises BINARYMIME [RFC3030].
    pub(super) fn validate_smtputf8_body(p: &crate::types::MailFromParams) -> Result<(), Error> {
        if p.smtputf8 && p.body == Some(crate::types::BodyType::SevenBit) {
            return Err(Error::Protocol(
                "BODY=7BIT cannot be used with SMTPUTF8; \
                 RFC 6531 Section 3.6 requires BODY=8BITMIME or \
                 BODY=BINARYMIME when SMTPUTF8 is used"
                    .into(),
            ));
        }
        Ok(())
    }

    /// RFC 6152 Section 3 / RFC 3030 Section 2: BODY type capability checks.
    ///
    /// BODY=7BIT is always accepted regardless of server capabilities
    /// because 7-bit is the default encoding (RFC 5321 Section 4.5.2).
    /// When the server does not advertise 8BITMIME, the encoder silently
    /// omits the redundant `BODY=7BIT` parameter.
    pub(super) fn validate_body_type(
        capabilities: &ServerCapabilities,
        p: &crate::types::MailFromParams,
    ) -> Result<(), Error> {
        // Explicit SevenBit arm kept for RFC-citation documentation;
        // its body matches the wildcard intentionally.
        #[allow(clippy::match_same_arms)]
        match p.body {
            // RFC 5321 Section 4.5.2: 7-bit is the default transfer
            // encoding — BODY=7BIT is a no-op declaration that does not
            // require 8BITMIME.  The encoder silently omits it when the
            // server lacks 8BITMIME support.
            Some(crate::types::BodyType::SevenBit) => {}
            Some(crate::types::BodyType::EightBitMime) if !capabilities.supports_8bitmime() => {
                return Err(Error::Protocol(
                    "BODY=8BITMIME requires server 8BITMIME support \
                     (RFC 6152 Section 3)"
                        .into(),
                ));
            }
            Some(crate::types::BodyType::BinaryMime) if !capabilities.supports_binarymime() => {
                return Err(Error::Protocol(
                    "BODY=BINARYMIME requires server BINARYMIME support \
                     (RFC 3030 Section 2)"
                        .into(),
                ));
            }
            Some(crate::types::BodyType::BinaryMime) if !capabilities.supports_chunking() => {
                return Err(Error::Protocol(
                    "BODY=BINARYMIME requires server CHUNKING support \
                     (RFC 3030 Section 2)"
                        .into(),
                ));
            }
            _ => {}
        }
        Ok(())
    }

    /// Validates that DSN RCPT TO parameters (NOTIFY, ORCPT) are only
    /// used when the server advertises DSN support.
    ///
    /// RFC 5321 Section 2.2.1: "An SMTP client MUST NOT use SMTP service
    /// extensions that have not been offered by the server."
    /// RFC 3461 Sections 4.1–4.2: NOTIFY and ORCPT are DSN extensions.
    pub(super) fn validate_rcpt_params(
        capabilities: &ServerCapabilities,
        rcpt_params: &[crate::types::RcptToParams],
    ) -> Result<(), Error> {
        let has_dsn_params = rcpt_params.iter().any(|p| !p.is_empty());
        if has_dsn_params && !capabilities.supports_dsn() {
            return Err(Error::Protocol(
                "DSN RCPT TO parameters (NOTIFY/ORCPT) require server DSN support \
                 (RFC 3461 Sections 4.1–4.2 / RFC 5321 Section 2.2.1)"
                    .into(),
            ));
        }
        Ok(())
    }

    /// Send EHLO or LHLO on a bare [`SmtpInner`], and parse capabilities.
    ///
    /// Used during both initial connection setup (before the mutex is
    /// constructed) and at runtime (with the guard dereferenced).
    ///
    /// SMTP uses EHLO (RFC 5321 Section 4.1.1.1). If EHLO is rejected,
    /// falls back to HELO (RFC 5321 Section 4.1.4).
    /// LMTP uses LHLO (RFC 2033 Section 4.1) with no HELO fallback.
    pub(super) async fn ehlo_on_inner(
        inner: &mut SmtpInner,
        protocol: Protocol,
    ) -> Result<(), Error> {
        // RFC 5321 Section 4.1.4: if we previously fell back to HELO
        // (server doesn't support ESMTP), continue using HELO for the
        // remainder of the session.  LMTP always uses LHLO.
        if inner.helo_mode && protocol == Protocol::Smtp {
            // RFC 5321 Section 4.1.1.1 publishes `helo = "HELO" SP Domain`
            // but also says that clients without a meaningful domain name
            // SHOULD send an address-literal. The domain is pre-validated
            // by the DomainOrLiteral type.
            let mut buf = BytesMut::new();
            encode::encode_helo(&mut buf, &inner.ehlo_domain)?;
            Self::validate_command_line_length(buf.len(), "HELO")?;
            inner.write_all(&buf).await?;
            let resp = inner.read_response().await?;
            if resp.code != 250 {
                if resp.is_success() {
                    return Err(Error::Protocol(format!(
                        "HELO response must be 250, got {} \
                         (RFC 5321 Section 4.1.1.1)",
                        resp.code
                    )));
                }
                return Err(Self::response_to_error(resp));
            }
            let greeting_name = resp
                .lines
                .first()
                .map(|l| match l.find(' ') {
                    Some(pos) => l[..pos].to_owned(),
                    None => l.clone(),
                })
                .unwrap_or_default();
            inner.capabilities = ServerCapabilities {
                greeting_name,
                ..Default::default()
            };
            return Ok(());
        }

        // The ehlo_domain is pre-validated by the DomainOrLiteral type.
        // RFC 5321 Section 4.1.1.1: the EHLO argument is a Domain or
        // address-literal. RFC 6531 (SMTPUTF8) does NOT extend this grammar.
        let mut buf = BytesMut::new();

        match protocol {
            Protocol::Smtp => encode::encode_ehlo(&mut buf, &inner.ehlo_domain)?,
            Protocol::Lmtp => encode::encode_lhlo(&mut buf, &inner.ehlo_domain)?,
        }
        // RFC 5321 Section 4.5.3.1.4: validate command line length.
        let cmd_name = match protocol {
            Protocol::Smtp => "EHLO",
            Protocol::Lmtp => "LHLO",
        };
        Self::validate_command_line_length(buf.len(), cmd_name)?;
        inner.write_all(&buf).await?;
        let resp = inner.read_response().await?;
        if resp.code == 250 {
            inner.capabilities = Self::parse_capabilities(&resp);
            return Ok(());
        }

        // RFC 5321 Section 4.1.1.1: EHLO success response MUST use
        // reply code 250. A non-250 2xx response does not conform to the
        // ehlo-ok-rsp grammar and must not be used to parse capabilities.
        if resp.is_success() {
            return Err(Error::Protocol(format!(
                "EHLO response must be 250, got {} \
                 (RFC 5321 Section 4.1.1.1)",
                resp.code
            )));
        }

        // RFC 5321 Section 4.1.4: EHLO rejection codes that warrant HELO fallback.
        // 500 = command not recognized (server doesn't speak ESMTP)
        // 501 = syntax error in parameters (server may not understand EHLO format)
        // 502 = command not implemented (server explicitly lacks ESMTP)
        // 504 = command parameter not implemented
        //
        // 550 is deliberately excluded — it indicates a policy rejection
        // of the client identity, not lack of ESMTP support. HELO fallback
        // would be futile and potentially mask the real issue.
        //
        // Other 5xx codes (e.g., 521 "does not accept mail" per RFC 7504,
        // or 554 "transaction failed") indicate problems unrelated to ESMTP
        // support where HELO won't help.
        //
        // Transient (4xx) errors like 421 ("service not available, closing
        // transmission channel") indicate a server-level problem, NOT that
        // the server doesn't support ESMTP. HELO fallback would be futile
        // in that case.
        //
        // LMTP has no HELO fallback (RFC 2033 Section 4.3: HELO is not
        // valid in LMTP).
        let helo_fallback_codes = [500, 501, 502, 504];
        if protocol == Protocol::Lmtp || !helo_fallback_codes.contains(&resp.code) {
            return Err(Self::response_to_error(resp));
        }

        tracing::debug!(
            code = resp.code,
            "EHLO rejected with 5xx, falling back to HELO (RFC 5321 Section 4.1.4)"
        );

        buf.clear();
        encode::encode_helo(&mut buf, &inner.ehlo_domain)?;
        // RFC 5321 Section 4.5.3.1.4: validate command line length.
        Self::validate_command_line_length(buf.len(), "HELO")?;
        inner.write_all(&buf).await?;
        let resp = inner.read_response().await?;
        // RFC 5321 Section 4.1.1.1: helo-ok-rsp = "250" SP Domain
        // [ SP helo-greet ] CRLF — only code 250 is valid for HELO success.
        if resp.code != 250 {
            if resp.is_success() {
                // Non-250 2xx — protocol violation, same treatment as EHLO.
                return Err(Error::Protocol(format!(
                    "HELO response must be 250, got {} \
                     (RFC 5321 Section 4.1.1.1)",
                    resp.code
                )));
            }
            return Err(Self::response_to_error(resp));
        }
        // HELO does not advertise extensions — use empty capabilities,
        // but preserve the server's greeting domain from the HELO response
        // (RFC 5321 Section 4.1.1.1: helo-ok-rsp = "250" SP Domain [ SP helo-greet ] CRLF).
        let greeting_name = resp
            .lines
            .first()
            .map(|l| match l.find(' ') {
                Some(pos) => l[..pos].to_owned(),
                None => l.clone(),
            })
            .unwrap_or_default();
        inner.capabilities = ServerCapabilities {
            greeting_name,
            ..Default::default()
        };
        // RFC 5321 Section 4.1.4: remember that this server doesn't
        // support ESMTP so subsequent rehlo calls use HELO too.
        inner.helo_mode = true;
        Ok(())
    }

    /// Parse EHLO/LHLO response lines into `ServerCapabilities`.
    ///
    /// Delegates to [`decode::parse_ehlo_capabilities`] which handles
    /// case-insensitive keyword matching (RFC 5321 Section 2.4) and
    /// preserves original mechanism names in `AuthMechanism::Other`
    /// (RFC 4954 Section 3).
    pub(super) fn parse_capabilities(response: &SmtpResponse) -> ServerCapabilities {
        decode::parse_ehlo_capabilities(response)
    }

    /// RFC 5321 Section 4.5.3.1.4: maximum total length of a command
    /// line including the command word and the `<CRLF>` is 512 octets.
    pub(super) const SMTP_MAX_COMMAND_LINE: usize = 512;

    /// Maximum total length of a MAIL FROM command line including
    /// ESMTP extension parameters (RFC 5321 Section 4.5.3.1.4).
    ///
    /// ESMTP extensions increase the base 512-octet limit:
    /// - RFC 1870 Section 4: +26 for the SIZE keyword and value
    /// - RFC 6152 Section 7: +17 for the BODY= parameter
    /// - RFC 6531 Section 3.4: +10 for the SMTPUTF8 keyword
    /// - RFC 8689 Section 3: +11 for the REQUIRETLS keyword
    /// - RFC 3461 Section 4.3/4.4: +109 for RET= and ENVID= params
    /// - RFC 4865 Section 5: +34 for HOLDFOR/HOLDUNTIL
    /// - RFC 2852 Section 4: +17 for BY= parameter
    /// - RFC 6758 Section 4: +16 for MT-PRIORITY= parameter
    /// - RFC 4954 Section 3: +500 for AUTH= submitter identity
    pub(super) const SMTP_MAX_MAIL_FROM_LINE: usize =
        512 + 26 + 17 + 10 + 11 + 109 + 34 + 17 + 16 + 500;

    /// RFC 3461 Section 5: maximum total length of a RCPT TO command
    /// line when DSN parameters (NOTIFY, ORCPT) are present.
    ///
    /// RFC 3461 Section 5 increases the RCPT TO line limit by 500 octets
    /// beyond the base 512-octet limit (RFC 5321 Section 4.5.3.1.4),
    /// yielding a maximum of 1012 octets.
    pub(super) const SMTP_MAX_RCPT_TO_DSN_LINE: usize = 1012;

    /// RFC 5321 Section 4.5.3.1.3: maximum total length of a
    /// reverse-path or forward-path including the punctuation
    /// and element separators (i.e., the `<` and `>` delimiters).
    ///
    /// Path-length validation is now performed by [`ReversePath::new`]
    /// and [`ForwardPath::new`] at construction time. This constant is
    /// retained for use in test assertions.
    #[cfg(test)]
    pub(super) const SMTP_MAX_PATH_LENGTH: usize = 256;

    /// Maximum reply line length the client will accept, including the
    /// 3-digit reply code and the terminating CRLF.
    ///
    /// RFC 5321 Section 4.5.3.1.5 specifies a 512-octet limit for
    /// compliant servers. However, per Postel's law ("be liberal in
    /// what you accept"), we use a permissive 8192-octet limit to
    /// tolerate non-conformant servers (e.g., Exchange, Postfix) that
    /// sometimes exceed the RFC limit in practice.
    pub(super) const SMTP_MAX_REPLY_LINE: usize = 8192;

    /// RFC 4954 Section 12: maximum length of an `auth-response` line
    /// (the base64-encoded SASL data sent during a two-step AUTH
    /// exchange), excluding the terminating CRLF.
    pub(super) const SMTP_MAX_AUTH_RESPONSE: usize = 12288;

    /// Maximum response buffer size (64 KiB).
    ///
    /// RFC 5321 Section 4.5.3.1.5 specifies reply lines should be at
    /// most 512 octets. We allow a generous 64 KiB to accommodate
    /// multi-line EHLO responses with many extensions, while still
    /// protecting against a malicious server exhausting memory.
    pub(super) const MAX_RESPONSE_BUFFER: usize = 64 * 1024;

    /// Try to parse a complete SMTP response from the buffer.
    ///
    /// Returns `None` if the buffer does not yet contain a complete response.
    /// On success, returns the parsed [`SmtpResponse`] together with the
    /// number of bytes consumed from `buf`, so the caller can advance past
    /// the response in a single step — eliminating the desynchronization
    /// risk of computing the byte length separately.
    ///
    /// Parses multi-line responses per RFC 5321 Section 4.2.
    pub(super) fn try_parse_response(buf: &[u8]) -> Result<Option<(SmtpResponse, usize)>, Error> {
        let mut lines = Vec::new();
        let mut code: Option<u16> = None;
        let mut first_enhanced: Option<EnhancedStatusCode> = None;
        let mut pos = 0;

        loop {
            // Find the next line ending: CRLF (RFC 5321 Section 2.3.8) or
            // bare LF (Postel's law — tolerate non-conformant servers that
            // omit CR, e.g., misconfigured Postfix, custom implementations).
            let (line_end_offset, terminator_len) = {
                let slice = &buf[pos..];
                // Find the earliest line terminator: CRLF (RFC 5321 Section 2.3.8)
                // or bare LF (Postel's law — tolerate non-conformant servers that
                // omit CR, e.g., misconfigured Postfix, custom implementations).
                // We must find the EARLIEST of the two to avoid merging two logical
                // response lines when bare LF precedes CRLF in the buffer.
                match slice.iter().position(|&b| b == b'\n') {
                    Some(lf_pos) if lf_pos > 0 && slice[lf_pos - 1] == b'\r' => {
                        // CRLF: the line content ends before the CR.
                        (lf_pos - 1, 2)
                    }
                    Some(lf_pos) => {
                        // Bare LF — tolerate per Postel's law (RFC 1122 Section 1.2.2).
                        (lf_pos, 1)
                    }
                    None => return Ok(None), // Incomplete — need more data.
                }
            };

            let line = &buf[pos..pos + line_end_offset];
            let line_total_len = line_end_offset + terminator_len; // line content + terminator

            // RFC 5321 Section 4.5.3.1.5: reply line should not exceed
            // 512 octets. We enforce a permissive limit of 8192 octets
            // per Postel's law to tolerate non-conformant servers.
            if line_total_len > Self::SMTP_MAX_REPLY_LINE {
                return Err(Error::Parse(format!(
                    "reply line exceeds {}-octet limit ({} octets) \
                     (RFC 5321 Section 4.5.3.1.5, relaxed per Postel's law)",
                    Self::SMTP_MAX_REPLY_LINE,
                    line_total_len
                )));
            }

            if line.len() < 3 {
                return Err(Error::Parse("response line too short".into()));
            }

            // Parse 3-digit reply code.
            let code_str = std::str::from_utf8(&line[..3])
                .map_err(|_| Error::Parse("invalid reply code bytes".into()))?;
            let line_code: u16 = code_str
                .parse()
                .map_err(|_| Error::Parse(format!("invalid reply code: {code_str}")))?;

            // RFC 5321 Section 4.2: reply-code = %x32-35 %x30-35 %x30-39
            // Strict ABNF limits the second digit to 0-5, but per Postel's
            // law we accept 0-9 to tolerate non-conformant servers.  The
            // first digit is still restricted to 2-5 (valid reply classes).
            let d0 = line[0];
            if !(b'2'..=b'5').contains(&d0) {
                return Err(Error::Parse(format!(
                    "reply code {line_code} outside valid range \
                     (RFC 5321 Section 4.2: first digit must be 2-5)"
                )));
            }

            // RFC 5321 Section 4.2: In a multi-line reply, every line MUST
            // use the same reply code.  A mismatch is a server protocol
            // violation, not a client-side parse failure.
            if let Some(c) = code {
                if c != line_code {
                    return Err(Error::Protocol(format!(
                        "reply code changed mid-response: {c} vs {line_code} \
                         (RFC 5321 Section 4.2)"
                    )));
                }
            }
            code = Some(line_code);

            // RFC 5321 Section 4.2: Reply-line separator must be '-'
            // (continuation), SP (final line with text), or absent
            // (code-only final line). Any other byte is invalid.
            let is_final = if line.len() == 3 {
                true // Just the code, no separator.
            } else {
                match line[3] {
                    b'-' => false,
                    b' ' => true,
                    other => {
                        return Err(Error::Parse(format!(
                            "invalid separator byte 0x{other:02X} at position 3 \
                             (RFC 5321 Section 4.2: expected '-' or SP)"
                        )));
                    }
                }
            };

            // Extract text after the separator.
            let raw_text = if line.len() > 4 {
                String::from_utf8_lossy(&line[4..]).into_owned()
            } else {
                String::new()
            };

            // Try to strip an enhanced status code from the start of the text
            // (RFC 2034 Section 3). Preserve only the first one found.
            // RFC 2034 Section 4: the enhanced code class MUST match the
            // reply code class — strip_enhanced_code validates this internally.
            let text = if let Some((esc, rest)) = decode::strip_enhanced_code(&raw_text, line_code)
            {
                if first_enhanced.is_none() {
                    first_enhanced = Some(esc);
                }
                rest.to_owned()
            } else {
                raw_text
            };
            lines.push(text);

            pos += line_end_offset + terminator_len; // Skip past line terminator.

            if is_final {
                let reply_code = code.ok_or_else(|| Error::Parse("empty response".into()))?;
                return Ok(Some((
                    SmtpResponse {
                        code: reply_code,
                        enhanced_code: first_enhanced,
                        lines,
                    },
                    pos,
                )));
            }
        }
    }

    /// Convert a non-success `SmtpResponse` into the appropriate `Error`.
    pub(super) fn response_to_error(resp: SmtpResponse) -> Error {
        let message = resp.text();
        let code = resp.code;
        if resp.is_permanent_error() {
            Error::Permanent {
                code,
                message,
                response: resp,
            }
        } else if resp.is_transient_error() {
            Error::Transient {
                code,
                message,
                response: resp,
            }
        } else {
            Error::Protocol(format!("unexpected response code {code}: {message}"))
        }
    }

    /// Create a default TLS configuration using the system root certificates.
    ///
    /// Installs the ring `CryptoProvider` if no provider has been set yet.
    pub(super) fn default_tls_config() -> Arc<rustls::ClientConfig> {
        // Install ring as the crypto provider (no-op if already installed).
        let _ = rustls::crypto::ring::default_provider().install_default();

        let root_store: rustls::RootCertStore =
            webpki_roots::TLS_SERVER_ROOTS.iter().cloned().collect();
        let config = rustls::ClientConfig::builder()
            .with_root_certificates(root_store)
            .with_no_client_auth();
        Arc::new(config)
    }

    /// Set the domain sent in EHLO/LHLO (RFC 5321 Section 4.1.1.1).
    ///
    /// The argument should be the client's FQDN or, when no FQDN is
    /// available, an address literal (RFC 5321 Section 4.1.4).
    ///
    /// Returns `Error::Protocol` if `domain` is empty or contains
    /// non-printable-ASCII bytes (RFC 5321 Section 4.1.1.1).
    ///
    /// This method acquires the internal mutex.
    pub async fn set_ehlo_domain(&self, domain: &str) -> Result<(), Error> {
        let domain = DomainOrLiteral::new(domain.to_owned())?;
        self.inner.lock().await.ehlo_domain = domain;
        Ok(())
    }
}