ci(email): gate multi-recipient send, and a gate that did not work

Two new gates, and one of them was broken when I first wrote it.

B1 gate: the send path must call email_send::parse_recipients, must NOT
contain a single-Mailbox parse of the whole To field, and must add every
accepted recipient. Three checks rather than one, because each failure
mode is separately reachable.

B5 gate: spawn_send_email must keep the SEND_IN_FLIGHT swap.

THE B5 GATE DID NOT WORK AS FIRST WRITTEN. It grepped the whole file for
`SEND_IN_FLIGHT.swap(true`, and the unit TESTS for the guard contain that
same string -- so deleting the guard from production code left the gate
green. I found it by negative-testing, which is the only reason I know.
Now scoped to the text before `#[cfg(test)]`.

That is worth recording rather than quietly fixing: a gate whose own test
fixtures satisfy it is indistinguishable from a gate that works, and the
only way to tell them apart is to break the thing on purpose.

Negative tests, all confirmed firing:
  remove the list parse                     -> fires
  reintroduce `let to_mbox: Mailbox = ..`   -> fires
  delete the in-flight guard                -> fires (after the fix)
and all 10 gates pass on the clean tree.

Test floor 60 -> 95 (actual 99).

Bulk page: builds through EmailSendRequest, so a partly-invalid list
reports what was dropped instead of refusing everything, and requires a
second tap before sending. The prompt quotes the recipient count and any
duplicates or rejections, so the user knows what they are confirming.
Editing the message after arming re-prompts rather than sending the old
confirmation.

.forgejo/workflows/email.yml

@@ -158,6 +158,62 @@ jobs:
           fi
           echo "OK"
 
+      # B1. The recipient field is labelled "To (comma-separated)" and the
+      # worker did `to.parse()` into a single lettre Mailbox, so ANY list
+      # failed with "Invalid to: ...". The tab named "Bulk" could reach
+      # exactly one person -- the crate's headline feature did not work.
+      #
+      # The send path must go through email_send::parse_recipients, and must
+      # add every accepted recipient rather than one.
+      - name: Multi-recipient send must not regress to a single mailbox
+        run: |
+          set -euo pipefail
+          bad=0
+          if ! grep -q 'email_send::parse_recipients' \
+                 crates/nigig-core/src/email_worker.rs; then
+            echo "ERROR: send_email_impl no longer parses the recipient list."
+            bad=1
+          fi
+          # The old shape, in non-comment code.
+          if grep -nE 'let[[:space:]]+to_mbox[[:space:]]*:[[:space:]]*Mailbox' \
+               crates/nigig-core/src/email_worker.rs \
+             | grep -vE '^[^:]*:[0-9]*:[[:space:]]*(//|///|/\*|\*)'; then
+            echo
+            echo "ERROR: a single-Mailbox parse of the whole To field is back."
+            echo "Mailbox::parse accepts ONE address; a comma-separated list"
+            echo "fails outright. Use email_send::parse_recipients."
+            bad=1
+          fi
+          if ! grep -q 'for r in &parsed.accepted' \
+                 crates/nigig-core/src/email_worker.rs; then
+            echo "ERROR: the builder no longer adds every recipient."
+            bad=1
+          fi
+          [ "$bad" -eq 0 ] || exit 1
+          echo "OK"
+
+      # B5. Both spawn_* functions used to fire unconditionally, so a double
+      # tap sent the message twice -- irreversible, to a real person. The
+      # guard is an AtomicBool swap, the same control robius-sms uses.
+      - name: A second concurrent send must be refused
+        run: |
+          set -euo pipefail
+          # Look only at PRODUCTION code. The unit tests for this guard
+          # also contain `SEND_IN_FLIGHT.swap(true`, so grepping the whole
+          # file passes even when spawn_send_email has lost the guard --
+          # which is exactly the regression this gate exists to catch. I
+          # found that by negative-testing: deleting the guard left the
+          # gate green.
+          prod=$(sed -n '1,/^#\[cfg(test)\]/p' \
+                   crates/nigig-core/src/email_worker.rs)
+          if ! echo "$prod" | grep -q 'SEND_IN_FLIGHT.swap(true'; then
+            echo "ERROR: the in-flight guard is gone from spawn_send_email."
+            echo "Without the swap, a double tap sends the message twice --"
+            echo "irreversible, to a real recipient."
+            exit 1
+          fi
+          echo "OK"
+
       # B3. `port.parse().unwrap_or(587)` silently rewrote a typo'd port,
       # and because the port selects the transport (465 implicit TLS vs
       # 587 STARTTLS) that silently changed the security posture too.
@@ -276,7 +332,7 @@ jobs:
       - name: The email domain test suite must not shrink
         run: |
           set -euo pipefail
-          FLOOR=60
+          FLOOR=95
           out="$(cargo test --locked -p nigig-core --lib -- email_ secret:: 2>&1)"
           echo "$out" | grep -E '^test result:' || true
           n=$(echo "$out" | grep -E '^test result:' \

REVIEWS/NIGIG_EMAIL_ASSESSMENT_AND_PLAN.md

@@ -532,6 +532,11 @@ snapshot. Commits are on `main`.
 
 **Phase 0 is complete.** All seven items done; 0.7 was fixed upstream.
 
+**Phase B is complete** (B6 partial by necessity). B1 was the live
+Critical: the field labelled "To (comma-separated)" was parsed by
+`Mailbox::parse`, which accepts ONE address, so every list failed and the
+tab named "Bulk" could reach exactly one person. Domain tests **72 → 99**.
+
 **Phase A is complete.** All six items done. The headline fix is A1/S2:
 `SmtpConfig` derived `Serialize` over a plaintext password and the whole
 struct was `serde_json`-encoded and POSTed on wasm. It now holds a
@@ -658,12 +663,12 @@ Negative tests: remove `#[serde(skip)]` → A1 gate fails. Set
 
 | ID | Task |
 |---|---|
-| B1 | **Multi-recipient send.** Parse the comma list into `Vec<Mailbox>`, report per-recipient success/failure. This is what "Bulk" claims to do. Reuse the SMS `recipient_csv.rs` normalisation approach for splitting/dedupe. |
+| ~~B1~~ | **DONE** — `email_send::parse_recipients`. Parse the comma list into `Vec<Mailbox>`, report per-recipient success/failure. This is what "Bulk" claims to do. Reuse the SMS `recipient_csv.rs` normalisation approach for splitting/dedupe. |
-| B2 | **`EmailSendRequest` domain type** in `nigig-core` with `validate()` — the seam that makes everything above testable. Mirrors `BulkSendRequest`. |
+| ~~B2~~ | **DONE** — `email_send.rs`. in `nigig-core` with `validate()` — the seam that makes everything above testable. Mirrors `BulkSendRequest`. |
-| B3 | **Move config assembly out of `handle_event`.** Read inputs on `.changed()` only, or read once at click time. Kills 10 allocations/event. |
+| ~~B3~~ | **DONE** (in Phase 0.3). Read inputs on `.changed()` only, or read once at click time. Kills 10 allocations/event. |
-| B4 | **Strict port parsing.** Empty → default *with a visible note*; invalid → refuse and say so. Never silently rewrite. |
+| ~~B4~~ | **DONE** — via `AccountDraft::validate`. Empty → default *with a visible note*; invalid → refuse and say so. Never silently rewrite. |
-| B5 | **In-flight guard + two-tap confirmation** before spending real sends (SMS A7/D5 pattern). |
+| ~~B5~~ | **DONE** — `SEND_IN_FLIGHT` + arm/confirm. before spending real sends (SMS A7/D5 pattern). |
-| B6 | **Timeout + cancel** on SMTP operations. No unbounded `"Testing..."`. |
+| ~~B6~~ | **PARTIAL** — 20s timeout + `abandon_send()`; true mid-transaction cancel is not possible, see note. on SMTP operations. No unbounded `"Testing..."`. |
 
 ---
 

crates/apps/nigig-email/src/email_frame/pages/bulk.rs

@@ -1,5 +1,6 @@
 use makepad_widgets::*;
 use nigig_core::email_account::AccountDraft;
+use nigig_core::email_send::EmailSendRequest;
 use nigig_core::email_worker::{spawn_send_email, spawn_smtp_test, EmailWorkerAction, SmtpConfig};
 
 script_mod! {
@@ -81,6 +82,11 @@ pub struct EmailBulkPage {
     view: View,
     #[rust]
     smtp_config: SmtpConfig,
+    /// B5: (body, recipient count) the user has been prompted about. A
+    /// second tap with the same pair confirms; anything else re-prompts, so
+    /// editing the message after arming cannot send the old confirmation.
+    #[rust]
+    pending_send: Option<(String, usize)>,
 }
 
 impl Widget for EmailBulkPage {
@@ -131,8 +137,50 @@ impl Widget for EmailBulkPage {
                 let subject = self.text_input(cx, ids!(subject_input)).text();
                 let message = self.text_input(cx, ids!(message_input)).text();
                 let config = self.smtp_config.clone();
-                self.label(cx, ids!(send_status)).set_text(cx, "Sending...");
+
-                spawn_send_email(config, to, subject, message);
+                // B1/B2: build through EmailSendRequest so the recipient
+                // list is actually parsed. This field is labelled
+                // "To (comma-separated)" and used to be handed to a single
+                // Mailbox parse, so any list failed outright.
+                match EmailSendRequest::build(&config, &to, &subject, &message) {
+                    Err(e) => {
+                        self.label(cx, ids!(send_status)).set_text(cx, &e.message());
+                        self.pending_send = None;
+                        self.view.redraw(cx);
+                    }
+                    Ok((req, list)) => {
+                        // B5: require a second tap before spending money.
+                        // Email is billed by nobody but it is irreversible
+                        // and goes to real people; the SMS crate requires
+                        // the same confirmation for the same reason.
+                        let n = req.recipient_count();
+                        let armed = self
+                            .pending_send
+                            .as_ref()
+                            .is_some_and(|(b, c)| b == &message && *c == n);
+
+                        if !armed {
+                            self.pending_send = Some((message.clone(), n));
+                            let mut prompt = format!(
+                                "Send to {} recipient{}? This cannot be undone. \
+                                 Tap Send again to confirm.",
+                                n,
+                                if n == 1 { "" } else { "s" }
+                            );
+                            if list.duplicates > 0 || !list.rejected.is_empty() {
+                                prompt.push_str(&format!(" ({})", list.summary()));
+                            }
+                            self.label(cx, ids!(send_status)).set_text(cx, &prompt);
+                            self.view.redraw(cx);
+                        } else {
+                            self.pending_send = None;
+                            self.label(cx, ids!(send_status))
+                                .set_text(cx, &format!("Sending to {n} recipient(s)…"));
+                            self.view.redraw(cx);
+                            spawn_send_email(config, to, subject, message);
+                        }
+                    }
+                }
             }
 
             for action in actions {

crates/nigig-core/src/email_account.rs

@@ -485,6 +485,55 @@ mod tests {
         assert_eq!(failed.account(), Some(&account));
     }
 
+    /// Every error must have a message. A missing arm here means the user
+    /// sees nothing when that validation fires.
+    #[test]
+    fn every_error_variant_has_a_usable_message() {
+        let all = [
+            AccountError::AddressMissing,
+            AccountError::AddressMalformed,
+            AccountError::ServerMissing,
+            AccountError::ServerMalformed,
+            AccountError::PortInvalid,
+            AccountError::UsernameMissing,
+            AccountError::PasswordMissing,
+        ];
+        for e in &all {
+            let m = e.message();
+            assert!(!m.is_empty(), "{e:?} has no message");
+            // Every message should tell the user what to DO, so it ends in
+            // a full stop and is a sentence, not a token.
+            assert!(m.ends_with('.'), "{e:?} message is not a sentence: {m}");
+            assert!(m.len() > 10, "{e:?} message is too terse: {m}");
+        }
+        // And they must be distinct, or the form cannot say which field is
+        // wrong.
+        let msgs: std::collections::HashSet<&str> =
+            all.iter().map(|e| e.message()).collect();
+        assert_eq!(msgs.len(), all.len(), "two errors share a message");
+    }
+
+    /// A present-but-malformed address is a different path from a missing
+    /// one, and it is the one a typo actually takes.
+    #[test]
+    fn a_malformed_address_is_reported_as_malformed_not_missing() {
+        let draft = AccountDraft {
+            address: "not-an-email".into(),
+            ..good_draft()
+        };
+        let errors = draft.validate().unwrap_err();
+        assert!(errors.contains(&AccountError::AddressMalformed));
+        assert!(!errors.contains(&AccountError::AddressMissing));
+    }
+
+    /// SignedOut and Verifying have no account to show; the form must not
+    /// be handed a stale one.
+    #[test]
+    fn states_without_an_account_return_none() {
+        assert_eq!(SessionState::SignedOut.account(), None);
+        assert_eq!(SessionState::Verifying.account(), None);
+    }
+
     #[test]
     fn status_lines_are_never_empty_and_name_the_account() {
         let (account, _) = good_draft().validate().unwrap();

crates/nigig-core/src/email_send.rs

@@ -0,0 +1,625 @@
+//! Recipient parsing and send-request validation.
+//!
+//! Phase B1/B2. The bulk page's recipient field is labelled
+//! `"To (comma-separated)"`, and the worker did:
+//!
+//! ```ignore
+//! let to_mbox: Mailbox = to.parse()?;   // ONE address
+//! ```
+//!
+//! `Mailbox` parses a single address, so any comma-separated list failed
+//! with `Invalid to: ...` -- the user got an error for doing exactly what
+//! the placeholder told them to do. The tab is named "Bulk" and could send
+//! to exactly one person.
+//!
+//! This module is the seam that fixes it, and it lives here rather than in
+//! the widget for the same reason `BulkSendRequest::validate` lives in
+//! `robius-sms`: recipient splitting is where the bugs are, none of it
+//! needs a network, and CI runs on a host with no SMTP server.
+//!
+//! Deliberately mirrors the SMS crate's `recipient_csv` approach --
+//! normalise, dedupe, skip bad rows with a reason rather than failing the
+//! whole input -- because the failure modes are the same and consistency
+//! between the two features is worth more than novelty.
+
+use crate::email_worker::{SmtpConfig, MAX_BODY_BYTES, MAX_SUBJECT_BYTES};
+
+/// One accepted recipient.
+#[derive(Clone, Debug, PartialEq, Eq)]
+pub struct Recipient {
+    /// The address, trimmed. Case is preserved: the local part is
+    /// technically case-sensitive per RFC 5321, even though virtually no
+    /// provider treats it that way.
+    pub address: String,
+    /// Display name if the input used `Name <addr>` form, else empty.
+    pub name: String,
+}
+
+impl Recipient {
+    /// Render back to something `lettre::Mailbox` can parse.
+    pub fn to_mailbox_string(&self) -> String {
+        if self.name.trim().is_empty() {
+            self.address.clone()
+        } else {
+            format!("{} <{}>", self.name.trim(), self.address)
+        }
+    }
+}
+
+/// Outcome of parsing a recipient field.
+#[derive(Clone, Debug, Default, PartialEq, Eq)]
+pub struct RecipientList {
+    pub accepted: Vec<Recipient>,
+    /// `(input_fragment, reason)` per rejected entry, so the UI can say
+    /// which one is wrong instead of just refusing.
+    pub rejected: Vec<(String, String)>,
+    /// Entries dropped because the address already appeared.
+    pub duplicates: usize,
+}
+
+impl RecipientList {
+    pub fn is_empty(&self) -> bool {
+        self.accepted.is_empty()
+    }
+
+    pub fn len(&self) -> usize {
+        self.accepted.len()
+    }
+
+    /// Addresses only, ready to hand to a transport.
+    pub fn addresses(&self) -> Vec<String> {
+        self.accepted.iter().map(|r| r.address.clone()).collect()
+    }
+
+    /// One-line summary for a status label.
+    pub fn summary(&self) -> String {
+        let mut s = format!(
+            "{} recipient{}",
+            self.accepted.len(),
+            if self.accepted.len() == 1 { "" } else { "s" }
+        );
+        if self.duplicates > 0 {
+            s.push_str(&format!(", {} duplicate(s) removed", self.duplicates));
+        }
+        if !self.rejected.is_empty() {
+            s.push_str(&format!(", {} rejected", self.rejected.len()));
+        }
+        s
+    }
+}
+
+/// Upper bound on recipients in one send.
+///
+/// Not a protocol limit. Providers cap RCPT TO per message -- commonly
+/// around 100 for consumer accounts -- and exceeding it fails the whole
+/// message rather than the excess. Refusing locally with a clear number is
+/// better than a provider error nobody can decode.
+pub const MAX_RECIPIENTS: usize = 100;
+
+/// Split a recipient field into addresses.
+///
+/// Accepts commas, semicolons and newlines as separators, because a user
+/// pasting from a spreadsheet or a mail client will produce any of them.
+///
+/// Handles `Display Name <addr@example.com>` including a quoted name that
+/// itself contains a comma -- `"Doe, Jane" <jane@x.com>` -- which a naive
+/// `split(',')` breaks in half. That form is common in pasted headers.
+pub fn parse_recipients(input: &str) -> RecipientList {
+    let mut out = RecipientList::default();
+    let mut seen: std::collections::HashSet<String> = std::collections::HashSet::new();
+
+    for raw in split_entries(input) {
+        let entry = raw.trim();
+        if entry.is_empty() {
+            continue;
+        }
+
+        let (name, address) = split_name_and_address(entry);
+
+        if !is_plausible_address(&address) {
+            out.rejected
+                .push((entry.to_string(), "not a valid email address".to_string()));
+            continue;
+        }
+
+        // Dedupe case-insensitively on the domain and, pragmatically, on
+        // the whole address: sending one person two copies of the same
+        // message is a bug that costs money and looks like spam.
+        let key = address.to_ascii_lowercase();
+        if !seen.insert(key) {
+            out.duplicates += 1;
+            continue;
+        }
+
+        out.accepted.push(Recipient { address, name });
+    }
+
+    out
+}
+
+/// Split on commas, semicolons and newlines, respecting double quotes and
+/// angle brackets.
+fn split_entries(input: &str) -> Vec<String> {
+    let mut parts = Vec::new();
+    let mut cur = String::new();
+    let mut in_quotes = false;
+    let mut in_angle = false;
+
+    for c in input.chars() {
+        match c {
+            '"' => {
+                in_quotes = !in_quotes;
+                cur.push(c);
+            }
+            '<' if !in_quotes => {
+                in_angle = true;
+                cur.push(c);
+            }
+            '>' if !in_quotes => {
+                in_angle = false;
+                cur.push(c);
+            }
+            ',' | ';' | '\n' | '\r' if !in_quotes && !in_angle => {
+                parts.push(std::mem::take(&mut cur));
+            }
+            _ => cur.push(c),
+        }
+    }
+    parts.push(cur);
+    parts
+}
+
+/// Pull `Name <addr>` apart. Returns `(name, address)`.
+fn split_name_and_address(entry: &str) -> (String, String) {
+    if let (Some(open), Some(close)) = (entry.rfind('<'), entry.rfind('>')) {
+        if open < close {
+            let addr = entry[open + 1..close].trim().to_string();
+            let name = entry[..open].trim().trim_matches('"').trim().to_string();
+            return (name, addr);
+        }
+    }
+    (String::new(), entry.trim().to_string())
+}
+
+/// Minimal address plausibility check.
+///
+/// Deliberately not an RFC 5322 grammar: that permits quoted local parts
+/// and comments no consumer provider accepts, and a strict implementation
+/// rejects addresses that work in practice. This checks what is always a
+/// mistake -- and rejecting here is cheap, because the real authority is
+/// the relay.
+pub fn is_plausible_address(s: &str) -> bool {
+    let s = s.trim();
+    if s.is_empty() || s.chars().any(char::is_whitespace) {
+        return false;
+    }
+    // Control characters would be a header-injection attempt. lettre
+    // encodes headers so this is defence in depth, but the C1d proxy
+    // backend does NOT go through lettre (see THREAT_MODEL T-E4), so the
+    // check belongs here rather than in the transport.
+    if s.chars().any(|c| c.is_control()) {
+        return false;
+    }
+    let mut it = s.split('@');
+    let (Some(local), Some(domain), None) = (it.next(), it.next(), it.next()) else {
+        return false;
+    };
+    !local.is_empty()
+        && !domain.is_empty()
+        && domain.contains('.')
+        && !domain.starts_with('.')
+        && !domain.ends_with('.')
+        && !domain.contains("..")
+}
+
+/// A validated send, ready for a transport.
+///
+/// B2: the seam the widget could not provide. `EmailBulkPage` built its
+/// request inline in `handle_event`, so none of it was testable without a
+/// `Cx`, and the Compose page could not reuse any of it -- which is why
+/// Compose has no send button at all.
+#[derive(Clone, Debug, PartialEq, Eq)]
+pub struct EmailSendRequest {
+    pub recipients: Vec<Recipient>,
+    pub subject: String,
+    pub body: String,
+}
+
+/// Why a send was refused.
+#[derive(Clone, Debug, PartialEq, Eq)]
+pub enum SendError {
+    ConfigIncomplete,
+    NoRecipients,
+    /// Every supplied recipient was malformed. Carries the reasons.
+    AllRecipientsInvalid(Vec<(String, String)>),
+    TooManyRecipients {
+        count: usize,
+        max: usize,
+    },
+    SubjectTooLong {
+        bytes: usize,
+        max: usize,
+    },
+    BodyTooLarge {
+        bytes: usize,
+        max: usize,
+    },
+    EmptyBody,
+}
+
+impl SendError {
+    /// Message shown to the user. Says what to change.
+    pub fn message(&self) -> String {
+        match self {
+            SendError::ConfigIncomplete => {
+                "Missing account settings. Check the server, port, username, \
+                 password and from address."
+                    .into()
+            }
+            SendError::NoRecipients => "Add at least one recipient.".into(),
+            SendError::AllRecipientsInvalid(bad) => {
+                let shown: Vec<String> = bad
+                    .iter()
+                    .take(3)
+                    .map(|(entry, why)| format!("{entry} ({why})"))
+                    .collect();
+                let mut m = format!("No valid recipients: {}", shown.join("; "));
+                if bad.len() > 3 {
+                    m.push_str(&format!(" and {} more", bad.len() - 3));
+                }
+                m
+            }
+            SendError::TooManyRecipients { count, max } => format!(
+                "{count} recipients is more than most providers accept in one \
+                 message. The limit here is {max}; split the list."
+            ),
+            SendError::SubjectTooLong { bytes, max } => {
+                format!("Subject is too long ({bytes} bytes). The limit is {max}.")
+            }
+            SendError::BodyTooLarge { bytes, max } => format!(
+                "Message is too large ({} MB). The limit is {} MB.",
+                bytes / (1024 * 1024),
+                max / (1024 * 1024)
+            ),
+            SendError::EmptyBody => "Type a message before sending.".into(),
+        }
+    }
+}
+
+impl EmailSendRequest {
+    /// Build and validate a send from raw UI strings.
+    ///
+    /// Returns the request plus any non-fatal notes (rejected or duplicate
+    /// recipients), so a partially-bad list still sends to the good
+    /// addresses and the user is told what was dropped. Failing the whole
+    /// batch because one address had a typo is the behaviour that made the
+    /// directory CSV importer unusable.
+    pub fn build(
+        config: &SmtpConfig,
+        to: &str,
+        subject: &str,
+        body: &str,
+    ) -> Result<(Self, RecipientList), SendError> {
+        if config.is_incomplete() {
+            return Err(SendError::ConfigIncomplete);
+        }
+
+        let list = parse_recipients(to);
+
+        if list.accepted.is_empty() {
+            return Err(if list.rejected.is_empty() {
+                SendError::NoRecipients
+            } else {
+                SendError::AllRecipientsInvalid(list.rejected.clone())
+            });
+        }
+        if list.accepted.len() > MAX_RECIPIENTS {
+            return Err(SendError::TooManyRecipients {
+                count: list.accepted.len(),
+                max: MAX_RECIPIENTS,
+            });
+        }
+        if subject.len() > MAX_SUBJECT_BYTES {
+            return Err(SendError::SubjectTooLong {
+                bytes: subject.len(),
+                max: MAX_SUBJECT_BYTES,
+            });
+        }
+        if body.trim().is_empty() {
+            return Err(SendError::EmptyBody);
+        }
+        if body.len() > MAX_BODY_BYTES {
+            return Err(SendError::BodyTooLarge {
+                bytes: body.len(),
+                max: MAX_BODY_BYTES,
+            });
+        }
+
+        Ok((
+            Self {
+                recipients: list.accepted.clone(),
+                subject: subject.to_string(),
+                body: body.to_string(),
+            },
+            list,
+        ))
+    }
+
+    pub fn recipient_count(&self) -> usize {
+        self.recipients.len()
+    }
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+    use crate::secret::Secret;
+
+    fn cfg() -> SmtpConfig {
+        SmtpConfig {
+            server: "smtp.example.com".into(),
+            port: SmtpConfig::DEFAULT_PORT,
+            username: "jane@example.com".into(),
+            password: Secret::new("hunter2"),
+            from: "jane@example.com".into(),
+        }
+    }
+
+    // ---- B1: the bug this module exists to fix -------------------------
+
+    /// THE regression test. The UI says "comma-separated"; before this,
+    /// a comma-separated list failed to parse entirely.
+    #[test]
+    fn a_comma_separated_list_yields_every_recipient() {
+        let list = parse_recipients("a@x.com, b@y.com, c@z.com");
+        assert_eq!(list.len(), 3, "rejected: {:?}", list.rejected);
+        assert_eq!(list.addresses(), vec!["a@x.com", "b@y.com", "c@z.com"]);
+        assert!(list.rejected.is_empty());
+    }
+
+    #[test]
+    fn semicolons_and_newlines_also_separate() {
+        assert_eq!(parse_recipients("a@x.com; b@y.com").len(), 2);
+        assert_eq!(parse_recipients("a@x.com\nb@y.com").len(), 2);
+        assert_eq!(parse_recipients("a@x.com\r\nb@y.com").len(), 2);
+        // Mixed, because pasted input is never tidy.
+        assert_eq!(
+            parse_recipients("a@x.com, b@y.com; c@z.com\nd@w.com").len(),
+            4
+        );
+    }
+
+    #[test]
+    fn a_single_address_still_works() {
+        let list = parse_recipients("solo@example.com");
+        assert_eq!(list.len(), 1);
+        assert_eq!(list.accepted[0].address, "solo@example.com");
+    }
+
+    // ---- display-name forms -------------------------------------------
+
+    #[test]
+    fn display_name_form_is_understood() {
+        let list = parse_recipients("Jane Doe <jane@example.com>");
+        assert_eq!(list.len(), 1);
+        assert_eq!(list.accepted[0].address, "jane@example.com");
+        assert_eq!(list.accepted[0].name, "Jane Doe");
+    }
+
+    /// A quoted name containing a comma must not be split in half. This is
+    /// the common shape when pasting from a mail client's To: header.
+    #[test]
+    fn a_quoted_name_containing_a_comma_is_one_recipient() {
+        let list = parse_recipients("\"Doe, Jane\" <jane@example.com>, bob@x.com");
+        assert_eq!(list.len(), 2, "rejected: {:?}", list.rejected);
+        assert_eq!(list.accepted[0].address, "jane@example.com");
+        assert_eq!(list.accepted[0].name, "Doe, Jane");
+        assert_eq!(list.accepted[1].address, "bob@x.com");
+    }
+
+    #[test]
+    fn mailbox_round_trip_preserves_the_name() {
+        let list = parse_recipients("Jane <jane@x.com>, bob@y.com");
+        assert_eq!(list.accepted[0].to_mailbox_string(), "Jane <jane@x.com>");
+        assert_eq!(list.accepted[1].to_mailbox_string(), "bob@y.com");
+    }
+
+    // ---- dedupe --------------------------------------------------------
+
+    /// Two copies of the same marketing email is a money bug.
+    #[test]
+    fn duplicates_are_collapsed_case_insensitively() {
+        let list = parse_recipients("a@x.com, A@X.COM, a@x.com");
+        assert_eq!(list.len(), 1);
+        assert_eq!(list.duplicates, 2);
+    }
+
+    // ---- rejection: partial failure must not fail the batch ------------
+
+    /// One bad address must not lose the good ones.
+    #[test]
+    fn bad_entries_are_rejected_without_dropping_the_good_ones() {
+        let list = parse_recipients("good@x.com, not-an-email, also-good@y.com");
+        assert_eq!(list.len(), 2);
+        assert_eq!(list.rejected.len(), 1);
+        assert_eq!(list.rejected[0].0, "not-an-email");
+    }
+
+    #[test]
+    fn rejects_what_is_always_a_mistake() {
+        for bad in [
+            "no-at-sign",
+            "@example.com",
+            "jane@",
+            "jane@nodot",
+            "two@at@signs.com",
+            "jane@.example.com",
+            "jane@example.",
+            "jane@ex..ample.com",
+        ] {
+            let list = parse_recipients(bad);
+            assert!(list.is_empty(), "should reject {bad:?}");
+            assert_eq!(list.rejected.len(), 1, "for {bad:?}");
+        }
+    }
+
+    /// Header injection. lettre encodes headers, but the C1d proxy backend
+    /// will not go through lettre, so this belongs here.
+    #[test]
+    fn control_characters_are_rejected() {
+        assert!(!is_plausible_address("a@x.com\rBcc: victim@y.com"));
+        assert!(!is_plausible_address("a@x.com\nBcc: victim@y.com"));
+        assert!(!is_plausible_address("a@x.com\0"));
+    }
+
+    #[test]
+    fn empty_input_yields_nothing_without_panicking() {
+        for s in ["", "   ", ",,,", "; ;", "\n\n"] {
+            let list = parse_recipients(s);
+            assert!(list.is_empty(), "for {s:?}");
+            assert!(
+                list.rejected.is_empty(),
+                "separators are not entries: {s:?}"
+            );
+        }
+    }
+
+    #[test]
+    fn summary_names_duplicates_and_rejections() {
+        let list = parse_recipients("a@x.com, a@x.com, bad");
+        let s = list.summary();
+        assert!(s.contains("1 recipient"), "got: {s}");
+        assert!(s.contains("duplicate"), "got: {s}");
+        assert!(s.contains("rejected"), "got: {s}");
+    }
+
+    // ---- B2: EmailSendRequest -----------------------------------------
+
+    #[test]
+    fn a_valid_send_builds() {
+        let (req, list) =
+            EmailSendRequest::build(&cfg(), "a@x.com, b@y.com", "Hi", "Body").unwrap();
+        assert_eq!(req.recipient_count(), 2);
+        assert_eq!(req.subject, "Hi");
+        assert!(list.rejected.is_empty());
+    }
+
+    #[test]
+    fn an_incomplete_config_is_refused_first() {
+        let bad = SmtpConfig {
+            server: String::new(),
+            ..cfg()
+        };
+        assert_eq!(
+            EmailSendRequest::build(&bad, "", "", "").unwrap_err(),
+            SendError::ConfigIncomplete
+        );
+    }
+
+    #[test]
+    fn no_recipients_and_all_invalid_are_different_errors() {
+        assert_eq!(
+            EmailSendRequest::build(&cfg(), "   ", "s", "b").unwrap_err(),
+            SendError::NoRecipients
+        );
+        match EmailSendRequest::build(&cfg(), "nope, also-nope", "s", "b").unwrap_err() {
+            SendError::AllRecipientsInvalid(bad) => assert_eq!(bad.len(), 2),
+            other => panic!("expected AllRecipientsInvalid, got {other:?}"),
+        }
+    }
+
+    /// A partially-bad list must still send to the good addresses.
+    #[test]
+    fn a_partly_invalid_list_still_builds_and_reports() {
+        let (req, list) = EmailSendRequest::build(&cfg(), "good@x.com, bad", "s", "b").unwrap();
+        assert_eq!(req.recipient_count(), 1);
+        assert_eq!(list.rejected.len(), 1);
+    }
+
+    #[test]
+    fn too_many_recipients_is_refused_with_the_limit() {
+        let many: Vec<String> = (0..MAX_RECIPIENTS + 1)
+            .map(|i| format!("u{i}@example.com"))
+            .collect();
+        match EmailSendRequest::build(&cfg(), &many.join(","), "s", "b").unwrap_err() {
+            SendError::TooManyRecipients { count, max } => {
+                assert_eq!(count, MAX_RECIPIENTS + 1);
+                assert_eq!(max, MAX_RECIPIENTS);
+            }
+            other => panic!("expected TooManyRecipients, got {other:?}"),
+        }
+    }
+
+    #[test]
+    fn exactly_the_recipient_limit_is_allowed() {
+        let many: Vec<String> = (0..MAX_RECIPIENTS)
+            .map(|i| format!("u{i}@example.com"))
+            .collect();
+        assert!(EmailSendRequest::build(&cfg(), &many.join(","), "s", "b").is_ok());
+    }
+
+    #[test]
+    fn an_empty_body_is_refused() {
+        assert_eq!(
+            EmailSendRequest::build(&cfg(), "a@x.com", "s", "   ").unwrap_err(),
+            SendError::EmptyBody
+        );
+    }
+
+    #[test]
+    fn an_over_long_subject_is_refused() {
+        let s = "a".repeat(MAX_SUBJECT_BYTES + 1);
+        assert!(matches!(
+            EmailSendRequest::build(&cfg(), "a@x.com", &s, "b").unwrap_err(),
+            SendError::SubjectTooLong { .. }
+        ));
+    }
+
+    #[test]
+    fn an_over_large_body_is_refused() {
+        let b = "a".repeat(MAX_BODY_BYTES + 1);
+        assert!(matches!(
+            EmailSendRequest::build(&cfg(), "a@x.com", "s", &b).unwrap_err(),
+            SendError::BodyTooLarge { .. }
+        ));
+    }
+
+    /// Every error must produce actionable text, or the user is stuck.
+    #[test]
+    fn every_send_error_has_a_distinct_actionable_message() {
+        let all = [
+            SendError::ConfigIncomplete,
+            SendError::NoRecipients,
+            SendError::AllRecipientsInvalid(vec![("x".into(), "why".into())]),
+            SendError::TooManyRecipients {
+                count: 200,
+                max: 100,
+            },
+            SendError::SubjectTooLong {
+                bytes: 2000,
+                max: 998,
+            },
+            SendError::BodyTooLarge {
+                bytes: 99_000_000,
+                max: 5_242_880,
+            },
+            SendError::EmptyBody,
+        ];
+        let mut seen = std::collections::HashSet::new();
+        for e in &all {
+            let m = e.message();
+            assert!(m.len() > 10, "{e:?} message too terse: {m}");
+            assert!(seen.insert(m.clone()), "duplicate message for {e:?}");
+        }
+    }
+
+    #[test]
+    fn the_all_invalid_message_lists_examples_and_truncates() {
+        let bad: Vec<(String, String)> = (0..6)
+            .map(|i| (format!("bad{i}"), "nope".to_string()))
+            .collect();
+        let m = SendError::AllRecipientsInvalid(bad).message();
+        assert!(m.contains("bad0"));
+        assert!(m.contains("and 3 more"), "got: {m}");
+    }
+}

crates/nigig-core/src/email_store.rs

@@ -432,6 +432,13 @@ mod tests {
         assert_eq!(out, "hello world");
     }
 
+    /// An empty body must still yield a row, not vanish.
+    #[test]
+    fn an_empty_body_previews_as_empty_without_panicking() {
+        assert_eq!(preview_line("", PREVIEW_CHARS), "");
+        assert_eq!(preview_line("   \n\t  ", PREVIEW_CHARS), "");
+    }
+
     #[test]
     fn short_bodies_are_returned_whole_without_an_ellipsis() {
         let out = preview_line("short", PREVIEW_CHARS);

crates/nigig-core/src/email_worker.rs

@@ -175,17 +175,88 @@ pub fn validate_send(
     Ok(())
 }
 
+/// True while a send is in flight.
+///
+/// B5: both `spawn_*` functions used to fire unconditionally, so a double
+/// tap on "Send Email" sent the message TWICE -- billed, irreversible, to a
+/// human recipient. The SMS crate hit exactly this and fixed it with an
+/// `AtomicBool` swap plus two-tap confirmation; email has the same
+/// irreversibility and had neither control.
+///
+/// Lives here rather than in the widget so every entry point is covered:
+/// the Bulk page, the Compose page, and anything added later.
+static SEND_IN_FLIGHT: std::sync::atomic::AtomicBool = std::sync::atomic::AtomicBool::new(false);
+
+/// Is a send currently running?
+pub fn send_in_flight() -> bool {
+    SEND_IN_FLIGHT.load(std::sync::atomic::Ordering::Relaxed)
+}
+
+/// Abandon the in-flight send's RESULT.
+///
+/// B6, and the honest scope of it. `tokio::spawn` hands back a
+/// `JoinHandle` that we do not retain, and `lettre`'s async send is not
+/// cancel-safe mid-transaction anyway: once DATA has been accepted the
+/// message is delivered whether we wait for the reply or not.
+///
+/// So this does NOT stop delivery. It clears the guard so the UI is usable
+/// again, and sets a flag the completion handler checks so a stale result
+/// does not overwrite whatever the user did next. Combined with
+/// `SMTP_TIMEOUT_SECS` (20s, vs lettre's 60s-per-command default) the
+/// window is bounded.
+///
+/// Naming it `abandon_send` rather than `cancel_send` on purpose: a
+/// function called cancel that does not cancel is worse than no function.
+pub fn abandon_send() {
+    SEND_ABANDONED.store(true, std::sync::atomic::Ordering::Relaxed);
+    SEND_IN_FLIGHT.store(false, std::sync::atomic::Ordering::Relaxed);
+}
+
+/// Set by `abandon_send`, cleared when a send starts.
+static SEND_ABANDONED: std::sync::atomic::AtomicBool = std::sync::atomic::AtomicBool::new(false);
+
+/// Was the in-flight send abandoned by the user?
+pub fn send_abandoned() -> bool {
+    SEND_ABANDONED.load(std::sync::atomic::Ordering::Relaxed)
+}
+
+/// Shown when a second send is attempted while one is running.
+pub const SEND_ALREADY_RUNNING: &str = "A send is already in progress.";
+
 /// Spawn an async email send task. Posts `EmailWorkerAction::SendResult` on completion.
 ///
 /// A4: validates locally first. Everything checked here is cheap and
 /// certain; nothing here needs a server to know it is wrong.
 pub fn spawn_send_email(config: SmtpConfig, to: String, subject: String, body: String) {
-    if let Err(msg) = validate_send(&config, &to, &subject, &body) {
+    // B4: validate through EmailSendRequest, which parses the recipient
-        Cx::post_action(EmailWorkerAction::SendResult(Err(msg)));
+    // list properly and reports which entry is wrong -- rather than the old
+    // path, which failed the whole send on the first bad address.
+    if let Err(e) = crate::email_send::EmailSendRequest::build(&config, &to, &subject, &body) {
+        Cx::post_action(EmailWorkerAction::SendResult(Err(e.message())));
         return;
     }
+
+    // B5: refuse a second concurrent send. `swap` is the guard: if it was
+    // already true we did not acquire it and must not clear it on the way
+    // out.
+    if SEND_IN_FLIGHT.swap(true, std::sync::atomic::Ordering::Relaxed) {
+        Cx::post_action(EmailWorkerAction::SendResult(Err(
+            SEND_ALREADY_RUNNING.to_string()
+        )));
+        return;
+    }
+    SEND_ABANDONED.store(false, std::sync::atomic::Ordering::Relaxed);
+
     crate::platform::spawn(async move {
         let result = send_email_impl(&config, &to, &subject, &body).await;
+        // Release before posting, so a UI that immediately retries on
+        // failure is not told a send is still running.
+        SEND_IN_FLIGHT.store(false, std::sync::atomic::Ordering::Relaxed);
+        // B6: if the user walked away, do not overwrite whatever they are
+        // looking at now with a result they stopped caring about.
+        if SEND_ABANDONED.swap(false, std::sync::atomic::Ordering::Relaxed) {
+            return;
+        }
         Cx::post_action(EmailWorkerAction::SendResult(result));
     });
 }
@@ -221,11 +292,30 @@ async fn send_email_impl(
         .from
         .parse()
         .map_err(|e| format!("Invalid from: {e}"))?;
-    let to_mbox: Mailbox = to.parse().map_err(|e| format!("Invalid to: {e}"))?;
+    // B1: the field is labelled "To (comma-separated)" and this used to be
-    let email = Message::builder()
+    // `to.parse()` into a single Mailbox, so ANY list failed with
-        .from(from_mbox)
+    // "Invalid to: ...". The tab named "Bulk" could reach exactly one
-        .to(to_mbox)
+    // person. Parse the list, then add every recipient.
-        .subject(subject)
+    let parsed = crate::email_send::parse_recipients(to);
+    if parsed.accepted.is_empty() {
+        return Err(if parsed.rejected.is_empty() {
+            "Add at least one recipient.".to_string()
+        } else {
+            format!(
+                "No valid recipients. First problem: {} ({})",
+                parsed.rejected[0].0, parsed.rejected[0].1
+            )
+        });
+    }
+    let mut builder = Message::builder().from(from_mbox).subject(subject);
+    for r in &parsed.accepted {
+        let mbox: Mailbox = r
+            .to_mailbox_string()
+            .parse()
+            .map_err(|e| format!("Invalid recipient {}: {e}", r.address))?;
+        builder = builder.to(mbox);
+    }
+    let email = builder
         .body(body.to_owned())
         .map_err(|e| format!("Build error: {e}"))?;
     let creds = Credentials::new(config.username.clone(), config.password.expose().to_owned());
@@ -588,6 +678,65 @@ mod tests {
         assert_eq!(err, INCOMPLETE_CONFIG_MESSAGE);
     }
 
+    // ---- B5/B6: the send guard ----------------------------------------
+
+    /// The guard is process-global, so these tests must not run in
+    /// parallel with each other. `cargo test` runs tests in threads, so
+    /// they share one lock rather than one static each.
+    static GUARD_LOCK: std::sync::Mutex<()> = std::sync::Mutex::new(());
+
+    #[test]
+    fn the_send_guard_starts_clear_and_admits_one_holder() {
+        let _g = GUARD_LOCK.lock().unwrap_or_else(|e| e.into_inner());
+        SEND_IN_FLIGHT.store(false, std::sync::atomic::Ordering::Relaxed);
+
+        assert!(!send_in_flight(), "must start clear");
+        // First acquire succeeds: swap returns the PREVIOUS value.
+        assert!(!SEND_IN_FLIGHT.swap(true, std::sync::atomic::Ordering::Relaxed));
+        assert!(send_in_flight());
+        // Second acquire sees it already held -- this is what stops a
+        // double tap sending twice (B5).
+        assert!(SEND_IN_FLIGHT.swap(true, std::sync::atomic::Ordering::Relaxed));
+
+        SEND_IN_FLIGHT.store(false, std::sync::atomic::Ordering::Relaxed);
+    }
+
+    #[test]
+    fn abandoning_a_send_releases_the_guard_and_marks_it_stale() {
+        let _g = GUARD_LOCK.lock().unwrap_or_else(|e| e.into_inner());
+        SEND_IN_FLIGHT.store(true, std::sync::atomic::Ordering::Relaxed);
+        SEND_ABANDONED.store(false, std::sync::atomic::Ordering::Relaxed);
+
+        abandon_send();
+
+        assert!(!send_in_flight(), "UI must be usable again");
+        assert!(send_abandoned(), "the pending result must be marked stale");
+
+        SEND_ABANDONED.store(false, std::sync::atomic::Ordering::Relaxed);
+        SEND_IN_FLIGHT.store(false, std::sync::atomic::Ordering::Relaxed);
+    }
+
+    /// The abandon flag is consumed once, so the send AFTER an abandoned
+    /// one still reports its result.
+    #[test]
+    fn the_abandon_flag_is_consumed_not_sticky() {
+        let _g = GUARD_LOCK.lock().unwrap_or_else(|e| e.into_inner());
+        SEND_ABANDONED.store(true, std::sync::atomic::Ordering::Relaxed);
+
+        // This is the swap the completion handler performs.
+        assert!(SEND_ABANDONED.swap(false, std::sync::atomic::Ordering::Relaxed));
+        assert!(
+            !send_abandoned(),
+            "a second send must not be suppressed too"
+        );
+    }
+
+    #[test]
+    fn the_already_running_message_is_actionable() {
+        assert!(SEND_ALREADY_RUNNING.len() > 10);
+        assert!(SEND_ALREADY_RUNNING.ends_with('.'));
+    }
+
     // ---- A4 follow-up: the from/username mismatch warning -------------
 
     #[test]

crates/nigig-core/src/lib.rs

@@ -20,6 +20,7 @@ pub mod syncing;
 pub mod tile_service;
 pub mod email_account;
 pub mod secret;
+pub mod email_send;
 pub mod email_store;
 pub mod email_worker;