@rapidmx/web-client 0.4.0 → 0.5.0

package/apps/shared/components/mail/compose/ComposeWindow.tsx

@@ -25,26 +25,29 @@ import {
     createDraft,
     deleteMessage,
     getMailbox,
+    getMessage,
     listFolders,
     listMailboxes,
     sendMessage,
     setMessageRequestReceipt,
-    setMessageScheduledSendTime,
     uploadAttachment,
 } from "@rapidmx/react-shared/mail/mailApi.js";
 import { listMailSignatures } from "@rapidmx/react-shared/mail/mailSignaturesApi.js";
+import { peekMailboxWritability, useMailboxWritability } from "../writableMailboxes.js";
 import { decideMessageEncryption, resolveRecipientEncryption, RecipientEncryptionStatus } from "@rapidmx/react-shared/crypto/composeSecurity.js";
-import { getUnlockedKeys } from "@rapidmx/react-shared/crypto/keySession.js";
+import { getUnlockedKeys, subscribeKeySession } from "@rapidmx/react-shared/crypto/keySession.js";
 import { EncryptionPolicy, findActivePublicKey, getEncryptionPolicy, lookupKeys } from "@rapidmx/react-shared/crypto/keyvaultApi.js";
 import { useUnlockPrompt } from "../../layout/UnlockPromptProvider.js";
 import { fromBase64 } from "@rapidmx/react-shared/crypto/encoding.js";
 import { ProtectedHeaders, applyBaselineOuterHeaders, assembleOutboundMime, buildEncryptedMessage, buildSignedOnlyMessage } from "@rapidmx/react-shared/crypto/smimeMessage.js";
 import useIsMobile from "@rapidmx/react-shared/util/useIsMobile.js";
 import type { ComposeSession } from "./ComposeContext.js";
+import { isSigningOut, registerComposeFlush } from "./composeFlushRegistry.js";
 import RichTextEditor from "./RichTextEditor.js";
 import ScheduleSendPicker from "./ScheduleSendPicker.js";
 import Alert from "@rapidmx/react-shared/components/feedback/Alert.js";
 import Button from "@rapidmx/react-shared/components/buttons/Button.js";
+import Modal from "@rapidmx/react-shared/components/overlays/Modal.js";
 
 export interface ComposeWindowProps {
     session: ComposeSession;
@@ -53,6 +56,77 @@ export interface ComposeWindowProps {
     /** The signed-in user - identifies their own ("primary") mailbox, the default From when the session
      * doesn't name a mailbox. */
     userUid?: string;
+    /** The caller holds a trusted (admin) role - every mailbox is writable, so no per-mailbox access checks. */
+    trusted?: boolean;
+    /** How long (ms) after the last edit the draft is autosaved. Defaults to `DEFAULT_AUTOSAVE_DELAY_MS`;
+     * only overridden by tests. */
+    autosaveDelayMs?: number;
+    /** Backoff (ms) between automatic retries of a failed mailbox/encryption-policy load, one entry per retry.
+     * Defaults to `DEFAULT_CRYPTO_RETRY_DELAYS_MS`; only overridden by tests. */
+    cryptoRetryDelaysMs?: number[];
+}
+
+/** Debounce between the last edit and the draft autosave. */
+export const DEFAULT_AUTOSAVE_DELAY_MS = 2000;
+
+/** Automatic retries of a failed mailbox/encryption-policy load; after the last one only "Retry" tries again. */
+export const DEFAULT_CRYPTO_RETRY_DELAYS_MS = [1000, 2000, 4000, 8000];
+
+/** Signed/encrypted bodies are built client-side from the editor's HTML verbatim, so an inline image
+ * (an uploaded attachment previewed via its content URL, or a `cid:` reference) would never be carried -
+ * only `assembleDraft()`'s server-side plaintext path rewrites those into real MIME parts. */
+const INLINE_IMAGE_PATTERN = /<img\b[^>]*\bsrc\s*=\s*["']?(?:cid:|[^"'\s>]*\/mail\/attachments\/[^"'\s>]+\/content)/i;
+
+const KEYS_LOCKED_SIGN_MESSAGE =
+    "This message can't be signed right now - your signing key is locked or your mailbox details couldn't be loaded. Unlock and send again, or send it without signing.";
+const KEYS_LOCKED_ENCRYPT_MESSAGE =
+    "This message can't be encrypted right now - your encryption key is locked. Unlock and send again, or send it without encryption.";
+const POLICY_UNAVAILABLE_MESSAGE =
+    "Your encryption settings couldn't be loaded, so this message can't be encrypted right now. Try again, or send it without encryption.";
+const BCC_ENCRYPTED_MESSAGE = "Bcc recipients can't be used with encrypted messages. Remove Bcc recipients or turn off encryption.";
+const LOOKUP_UNAVAILABLE_MESSAGE =
+    "Your recipients' encryption keys couldn't be checked, so this message might go out unencrypted when it should be encrypted. Try again, or send it without encryption.";
+/** Thrown by `deleteDraft()` when the server copy is no longer this window's draft (sent or scheduled elsewhere). */
+const NO_LONGER_A_DRAFT_MESSAGE = "This message was already sent or scheduled from another window, so it wasn't deleted.";
+
+/** The server refuses signed/encrypted mail whose From display name differs from its own safe form, which drops a
+ * name containing `@` (or a look-alike) or a line break. */
+const UNSAFE_DISPLAY_NAME_PATTERN = /[@＠﹫\r\n]/;
+
+/** Whether `fresh` (a re-read of a draft) is still an unsent draft in `folderUid`: never delete a message another
+ * window has since sent, scheduled, or started sending. */
+function isStillDraft(fresh: Message, folderUid: string): boolean {
+    return fresh.folderUid === folderUid && !fresh.scheduledSendTime && !fresh.scheduledSendLeaseExpiresAt && !fresh.scheduledSendRelayedAt;
+}
+
+/** Any tier of `policy` auto-encrypts - only then can a message with recipients still to be added turn out encrypted
+ * without the user asking. */
+function policyCanAutoEncrypt(policy: EncryptionPolicy): boolean {
+    return [policy.encryptSameOrg, policy.encryptFederated, policy.encryptExternal].includes("automatic");
+}
+
+const SAVE_STATUS_LABEL = { idle: "", saving: "Saving…", saved: "Draft saved", error: "Couldn't save draft" } as const;
+
+const DISCARD_TITLE = "Discard this draft?";
+const ENCRYPTED_CLOSE_MESSAGE = "Encrypted messages aren't saved as drafts, so closing this window discards what you've written.";
+const CHECKING_CLOSE_MESSAGE =
+    "This message may be encrypted, and that's still being checked, so it can't be saved as a draft yet. Keep editing and close again in a moment, or discard it.";
+const CRYPTO_UNAVAILABLE_MESSAGE =
+    "Your encryption settings couldn't be checked, so this draft isn't being saved - it might be a message that must be encrypted.";
+const NO_RECIPIENTS_CLOSE_MESSAGE =
+    "This message may be encrypted once its recipients are known, so it isn't saved as a draft until you add them. Add a recipient and close again, or discard it.";
+
+/** The confirmation shown before a Close/Discard throws content away (or when a Close couldn't save it). */
+interface ClosePrompt {
+    title: string;
+    message: string;
+    /** Also offer "Retry" for loading the encryption settings. */
+    retry?: boolean;
+}
+
+interface SecurityBlock {
+    message: string;
+    overrideLabel: string;
 }
 
 const FIELD_ROW = "flex items-center gap-2 px-3 py-1.5 border-b border-border";
@@ -83,14 +157,25 @@ function parseAddresses(value: string): ComposeRecipientInput[] {
         .map((address) => ({ address }));
 }
 
-function HeaderButton({ label, onClick, icon: Icon }: { label: string; onClick: () => void; icon: React.ComponentType<{ size?: number }> }) {
+function HeaderButton({
+    label,
+    onClick,
+    icon: Icon,
+    disabled,
+}: {
+    label: string;
+    onClick: () => void;
+    icon: React.ComponentType<{ size?: number }>;
+    disabled?: boolean;
+}) {
     return (
         <button
             type="button"
             aria-label={label}
             title={label}
             onClick={onClick}
-            className="w-6 h-6 flex items-center justify-center rounded-sm text-white/80 hover:bg-white/15 hover:text-white"
+            disabled={disabled}
+            className="w-6 h-6 flex items-center justify-center rounded-sm text-white/80 hover:bg-white/15 hover:text-white disabled:opacity-40 disabled:cursor-not-allowed"
         >
             <Icon size={14} />
         </button>
@@ -111,7 +196,15 @@ function HeaderButton({ label, onClick, icon: Icon }: { label: string; onClick:
  * see `ComposeContext.tsx`'s own doc comment for how that interacts with several sessions being open at
  * once.
  */
-export default function ComposeWindow({ session, onClose, onToggleMinimize, userUid }: ComposeWindowProps) {
+export default function ComposeWindow({
+    session,
+    onClose,
+    onToggleMinimize,
+    userUid,
+    trusted,
+    autosaveDelayMs = DEFAULT_AUTOSAVE_DELAY_MS,
+    cryptoRetryDelaysMs = DEFAULT_CRYPTO_RETRY_DELAYS_MS,
+}: ComposeWindowProps) {
     const { id, initialTo, initialCc, initialSubject, initialQuotedHtml, signatureContext, suppressSigning, minimized } = session;
     // The sending ("From") mailbox. A reply/forward session names the original message's mailbox; a fresh
     // compose leaves it unset and defaults to the caller's own mailbox once `listMailboxes()` resolves.
@@ -132,6 +225,8 @@ export default function ComposeWindow({ session, onClose, onToggleMinimize, user
     const [draftsFolderUid, setDraftsFolderUid] = useState<string | undefined>();
     const [folderError, setFolderError] = useState<string | null>(null);
     const [draft, setDraft] = useState<Message | null>(null);
+    // Drafts replaced by a From switch, awaiting deletion until their replacement has actually been created.
+    const supersededDraftsRef = useRef<Message[]>([]);
     const [draftError, setDraftError] = useState<string | null>(null);
     const [expanded, setExpanded] = useState(false);
     const [manualSize, setManualSize] = useState<Size | null>(null);
@@ -163,13 +258,58 @@ export default function ComposeWindow({ session, onClose, onToggleMinimize, user
     // just because the user re-focuses the field. Only ever grows via `checkRecipientDiscovery()` below;
     // never cleared, so switching focus between To/Cc/Bcc repeatedly doesn't re-trigger lookups.
     const [recipientStatuses, setRecipientStatuses] = useState<Record<string, RecipientEncryptionStatus>>({});
+    // Addresses whose lookup is on the wire (so the blur handlers and the prefilled-recipient effect don't
+    // look one up twice), and a counter bumped by a From switch so a lookup for the previous sender is dropped.
+    const lookupsInFlightRef = useRef(new Set<string>());
+    const discoveryGenerationRef = useRef(0);
+    // A failed lookup stores no status (it would read as "no key" and let a message that must be encrypted autosave
+    // or send as plaintext): it's retried with the same backoff as the mailbox/policy load, and once those retries
+    // run out the address is "exhausted" - shown as a check that couldn't be done, with Retry.
+    const lookupFailuresRef = useRef(new Map<string, number>());
+    const lookupRetryTimersRef = useRef(new Set<ReturnType<typeof setTimeout>>());
+    const [lookupRetryToken, setLookupRetryToken] = useState(0);
+    const [exhaustedLookups, setExhaustedLookups] = useState<Record<string, true>>({});
+    // A send refused because signing/encryption was wanted but can't happen right now (keys locked, the
+    // encryption policy/mailbox couldn't be loaded, or Bcc recipients on an encrypted message) - never a
+    // silent downgrade to plaintext; the user has to explicitly pick the override.
+    const [securityBlock, setSecurityBlock] = useState<SecurityBlock | null>(null);
+    // The schedule time of the send that got blocked (undefined for an immediate send), so the banners'
+    // override buttons replay the same kind of send the user originally asked for.
+    const [blockedScheduleIso, setBlockedScheduleIso] = useState<string | undefined>();
+    // Which crypto toggles were ever shown during this compose session (per sending mailbox). Keys that
+    // lock after that point must block the send rather than quietly dropping the signature/encryption.
+    const offeredCryptoRef = useRef({ sign: false, encrypt: false });
+
+    // Draft autosave / discard bookkeeping.
+    const [seededHtml, setSeededHtml] = useState<string | undefined>();
+    const [saveStatus, setSaveStatus] = useState<"idle" | "saving" | "saved" | "error">("idle");
+    const [closePrompt, setClosePrompt] = useState<ClosePrompt | null>(null);
+    /** A Close (saving) or Discard (deleting) is on the wire - the window closes once it succeeds. */
+    const [closing, setClosing] = useState(false);
+    const [discardError, setDiscardError] = useState<string | null>(null);
+    /** Why the last save failed, cleared by the next successful one. */
+    const saveErrorRef = useRef<string | null>(null);
+    /** `<draftUid>:<content key>` of the last successful save. */
+    const lastSavedRef = useRef<string | null>(null);
+    /** An edit is waiting on the autosave debounce - flushed if the window unmounts first. */
+    const pendingSaveRef = useRef(false);
+    /** Mirrors `sending` for the page-leave/sign-out flushes, which run outside React's render cycle. */
+    const sendingRef = useRef(false);
+    /** The latest save request, if any - each save is chained after the one before it. Always settles (never
+     * rejects), to the saved message, or `undefined` when that save failed. */
+    const saveInFlightRef = useRef<Promise<Message | undefined>>(Promise.resolve(undefined));
+    /** Set once the window has been sent/closed/discarded - nothing more gets autosaved after that. */
+    const finishedRef = useRef(false);
 
-    // Best-effort, same as the signature-list fetch below: a mailbox with no keys enrolled yet (or a
-    // failed fetch) just means sign/encrypt stay unavailable for this compose session, never a blocking
-    // error - encryption is optional and gradual by design (see `KeyEnrollmentGate`'s own doc comment).
+    // A mailbox with no keys enrolled yet just means sign/encrypt stay unavailable for this compose session -
+    // encryption is optional and gradual by design (see `KeyEnrollmentGate`'s own doc comment).
     // `cryptoContextReady` (below) gates Send/Send-later until both calls have settled either way, so a
     // send that happens to race this fetch can't silently skip encryption the spec says should apply.
+    // A failed load is retried with backoff (`cryptoRetryDelaysMs`), then on demand ("Retry"): until both have
+    // loaded, whether this message must be encrypted is unknown, so it isn't autosaved (see `autosaveSuppressed`).
     const [cryptoContextReady, setCryptoContextReady] = useState(false);
+    const [cryptoLoadFailed, setCryptoLoadFailed] = useState(false);
+    const [cryptoRetryToken, setCryptoRetryToken] = useState(0);
 
     useEffect(() => {
         let cancelled = false;
@@ -179,7 +319,10 @@ export default function ComposeWindow({ session, onClose, onToggleMinimize, user
                     return;
                 }
                 setMailboxes(result);
-                setFromMailboxUid((current) => current ?? (result.find((mb) => mb.ownerUserUid === userUid) ?? result[0])?.uid);
+                // Never default to a mailbox already known to be view-only (see the effect below for one
+                // that turns out to be).
+                const candidates = result.filter((mb) => peekMailboxWritability(mb, userUid, trusted) !== false);
+                setFromMailboxUid((current) => current ?? (candidates.find((mb) => mb.ownerUserUid === userUid) ?? candidates[0])?.uid);
             })
             .catch((err) => {
                 // Only fatal when there's no mailbox to fall back on - a session that already names one just
@@ -191,7 +334,6 @@ export default function ComposeWindow({ session, onClose, onToggleMinimize, user
         return () => {
             cancelled = true;
         };
-        // eslint-disable-next-line react-hooks/exhaustive-deps
     }, []);
 
     useEffect(() => {
@@ -199,40 +341,52 @@ export default function ComposeWindow({ session, onClose, onToggleMinimize, user
             return;
         }
         let cancelled = false;
+        let timer: ReturnType<typeof setTimeout> | undefined;
+        // A retry only fetches what's still missing.
+        let mailboxLoaded = mailbox?.uid === mailboxUid;
+        let policyLoaded = !!encryptionPolicy;
+        let retries = 0;
         setCryptoContextReady(false);
-        let mailboxSettled = false;
-        let policySettled = false;
-        function checkReady() {
-            if (!cancelled && mailboxSettled && policySettled) {
-                setCryptoContextReady(true);
+        setCryptoLoadFailed(false);
+        async function load() {
+            await Promise.all([
+                mailboxLoaded ||
+                    getMailbox(mailboxUid!).then(
+                        (result) => {
+                            mailboxLoaded = true;
+                            if (!cancelled) {
+                                setMailbox(result);
+                            }
+                        },
+                        () => undefined,
+                    ),
+                policyLoaded ||
+                    getEncryptionPolicy().then(
+                        (result) => {
+                            policyLoaded = true;
+                            if (!cancelled) {
+                                setEncryptionPolicy(result);
+                            }
+                        },
+                        () => undefined,
+                    ),
+            ]);
+            if (cancelled) {
+                return;
+            }
+            const failed = !mailboxLoaded || !policyLoaded;
+            setCryptoContextReady(true);
+            setCryptoLoadFailed(failed);
+            if (failed && retries < cryptoRetryDelaysMs.length) {
+                timer = setTimeout(() => void load(), cryptoRetryDelaysMs[retries++]);
             }
         }
-        getMailbox(mailboxUid)
-            .then((result) => {
-                if (!cancelled) {
-                    setMailbox(result);
-                }
-            })
-            .catch(() => undefined)
-            .finally(() => {
-                mailboxSettled = true;
-                checkReady();
-            });
-        getEncryptionPolicy()
-            .then((result) => {
-                if (!cancelled) {
-                    setEncryptionPolicy(result);
-                }
-            })
-            .catch(() => undefined)
-            .finally(() => {
-                policySettled = true;
-                checkReady();
-            });
+        void load();
         return () => {
             cancelled = true;
+            clearTimeout(timer);
         };
-    }, [mailboxUid]);
+    }, [mailboxUid, cryptoRetryToken]);
 
     useEffect(() => {
         if (!mailboxUid) {
@@ -263,25 +417,74 @@ export default function ComposeWindow({ session, onClose, onToggleMinimize, user
      * without waiting for Send. Called from the To/Cc/Bcc fields' own `onBlur` - not on every keystroke,
      * and not the same lookup `assembleForSend()` performs again at send time (deliberately: this is a
      * best-effort UI hint, not something a stale value here should be trusted to skip at send time).
-     * A failed lookup or a mailbox/policy fetch that hasn't resolved yet just leaves that address with no
-     * indicator rather than surfacing an error over what's a cosmetic nicety.
+     * A mailbox/policy fetch that hasn't resolved yet just leaves that address with no indicator - the effect
+     * below runs it again for every current recipient once both have loaded. A failed lookup leaves it without
+     * a status too, and is retried after `cryptoRetryDelaysMs` (then only on blur, Close or Retry).
+     *
+     * The statuses also drive autosave: a recipient without one yet (lookup pending, failed or never run) or a
+     * decision that would auto-encrypt keeps the plaintext draft save off (see `autosaveSuppressed`).
      */
     function checkRecipientDiscovery(addresses: ComposeRecipientInput[]) {
         if (!mailbox || !encryptionPolicy) {
             return;
         }
         const ownPrefersMutual = mailbox.encryptPreference?.preferEncrypt === "mutual";
-        const unchecked = addresses.filter((r) => !(r.address in recipientStatuses));
+        const generation = discoveryGenerationRef.current;
+        const inFlight = lookupsInFlightRef.current;
+        const unchecked = addresses.filter((r) => !(r.address in recipientStatuses) && !inFlight.has(r.address));
         for (const recipient of unchecked) {
-            lookupKeys(mailbox.uid, recipient.address)
-                .catch(() => undefined)
-                .then((lookup) => {
-                    const status = resolveRecipientEncryption(mailbox.primarySmtpAddress, ownPrefersMutual, encryptionPolicy, recipient.address, lookup);
+            inFlight.add(recipient.address);
+            void lookupKeys(mailbox.uid, recipient.address)
+                .then(
+                    (lookup) => ({ lookup }),
+                    () => null,
+                )
+                .then((result) => {
+                    inFlight.delete(recipient.address);
+                    if (generation !== discoveryGenerationRef.current) {
+                        return;
+                    }
+                    if (!result) {
+                        noteLookupFailed(recipient.address);
+                        return;
+                    }
+                    lookupFailuresRef.current.delete(recipient.address);
+                    const status = resolveRecipientEncryption(mailbox.primarySmtpAddress, ownPrefersMutual, encryptionPolicy, recipient.address, result.lookup);
                     setRecipientStatuses((prev) => ({ ...prev, [recipient.address]: status }));
                 });
         }
     }
 
+    /** Schedules the next automatic retry of a failed lookup, or marks the address exhausted once they've run out. */
+    function noteLookupFailed(address: string) {
+        const failures = (lookupFailuresRef.current.get(address) ?? 0) + 1;
+        lookupFailuresRef.current.set(address, failures);
+        if (failures > cryptoRetryDelaysMs.length) {
+            setExhaustedLookups((prev) => ({ ...prev, [address]: true }));
+            return;
+        }
+        const timer = setTimeout(() => {
+            lookupRetryTimersRef.current.delete(timer);
+            setLookupRetryToken((n) => n + 1);
+        }, cryptoRetryDelaysMs[failures - 1]);
+        lookupRetryTimersRef.current.add(timer);
+    }
+
+    useEffect(
+        () => () => {
+            for (const timer of lookupRetryTimersRef.current) {
+                clearTimeout(timer);
+            }
+        },
+        [],
+    );
+
+    // Prefilled recipients (a reply's To/Cc) are never blurred, and a blur before the mailbox/policy loaded
+    // was ignored - look every current recipient up as soon as both are available (and again on a lookup retry).
+    useEffect(() => {
+        checkRecipientDiscovery([...parseAddresses(to), ...parseAddresses(cc), ...parseAddresses(bcc)]);
+    }, [mailbox, encryptionPolicy, lookupRetryToken]);
+
     // Resolves the mailbox's default signature (if any) for `signatureContext` and seeds `html` with it
     // plus any quoted original message, before `RichTextEditor` ever mounts (gated by `contentReady`
     // below) — `RichTextEditor`'s own doc comment is explicit that `value` only seeds its *initial*
@@ -302,9 +505,14 @@ export default function ComposeWindow({ session, onClose, onToggleMinimize, user
                     signatureContext === "new" ? s.isDefaultForNewMessages : s.isDefaultForReplyForward,
                 );
                 const signatureHtml = signature?.contentHtml ? `${signature.contentHtml}<p></p>` : "";
-                setHtml(`${signatureHtml}${initialQuotedHtml ?? ""}`);
+                const seeded = `${signatureHtml}${initialQuotedHtml ?? ""}`;
+                setHtml(seeded);
+                setSeededHtml(seeded);
+            })
+            .catch(() => {
+                setHtml(initialQuotedHtml ?? "");
+                setSeededHtml(initialQuotedHtml ?? "");
             })
-            .catch(() => setHtml(initialQuotedHtml ?? ""))
             .finally(() => setContentReady(true));
     }, [mailboxUid, signatureContext, initialQuotedHtml]);
 
@@ -321,6 +529,11 @@ export default function ComposeWindow({ session, onClose, onToggleMinimize, user
                     return;
                 }
                 setDraft(created);
+                // Only now that the replacement exists is it safe to discard the draft(s) a From switch
+                // superseded - if creating this one had failed, the earlier draft is still there.
+                for (const superseded of supersededDraftsRef.current.splice(0)) {
+                    void deleteSupersededDraft(superseded);
+                }
             })
             .catch((err) => {
                 if (!cancelled) {
@@ -332,15 +545,72 @@ export default function ComposeWindow({ session, onClose, onToggleMinimize, user
         };
     }, [mailboxUid, draftsFolderUid, draft]);
 
-    /** Switches the sending mailbox: discards the current (unsent, upload-free) draft and resets the
-     * per-mailbox state, so the effects above start a fresh draft and crypto context in the new mailbox.
-     * Recipients, subject, and body are kept. */
+    // Drafts a From switch superseded are otherwise only deleted once their replacement exists - closing the
+    // window (or sending, which closes it) first would orphan them.
+    useEffect(
+        () => () => {
+            for (const superseded of supersededDraftsRef.current.splice(0)) {
+                void deleteSupersededDraft(superseded);
+            }
+        },
+        [],
+    );
+
+    /**
+     * Deletes a draft a From switch replaced. An autosave of it may still be on the wire - it bumps the
+     * draft's version (see `saveDraftNow()`, which keeps `superseded.version` current while it's queued), so
+     * the delete waits for it and uses its version; a delete that still fails (e.g. another save of it landed
+     * meanwhile) is retried once with the version the server currently holds - unless it's no longer a draft
+     * (another window sent or scheduled it), which is left alone.
+     * Best-effort, never rejects.
+     */
+    async function deleteSupersededDraft(superseded: Message): Promise<void> {
+        const saved = await saveInFlightRef.current;
+        // Once it's out of `supersededDraftsRef` a landing save can't update `superseded.version` any more.
+        const version = saved?.uid === superseded.uid ? saved.version : superseded.version;
+        try {
+            await deleteMessage(superseded.uid, version);
+        } catch {
+            try {
+                const fresh = await getMessage(superseded.uid);
+                if (isStillDraft(fresh, superseded.folderUid)) {
+                    await deleteMessage(fresh.uid, fresh.version);
+                }
+            } catch {
+                // Already gone, or the server is unreachable - nothing more to do from here.
+            }
+        }
+    }
+
+    // The From picker lists every mailbox straight away and drops view-only ones as each check answers - only
+    // mailboxes the caller can create a draft in are worth offering.
+    const writability = useMailboxWritability(mailboxes, userUid, trusted);
+    const fromOptions = mailboxes.filter((mb) => mb.uid === mailboxUid || writability[mb.uid] !== false);
+
+    // The sender turned out to be view-only (e.g. a reply to a message in a mailbox shared read-only, or a
+    // first-listed shared mailbox): switch to one the caller can actually send from, preferring their own.
+    const fromIsViewOnly = !!mailboxUid && writability[mailboxUid] === false;
+    useEffect(() => {
+        if (!fromIsViewOnly || hasUploads) {
+            return;
+        }
+        const ordered = [...mailboxes.filter((mb) => mb.ownerUserUid === userUid), ...mailboxes.filter((mb) => mb.ownerUserUid !== userUid)];
+        const alternative = ordered.find((mb) => writability[mb.uid] === true) ?? ordered.find((mb) => writability[mb.uid] === undefined);
+        if (alternative) {
+            handleFromChange(alternative.uid);
+        }
+    }, [fromIsViewOnly, writability]);
+
+    /** Switches the sending mailbox: supersedes the current (unsent, upload-free) draft and resets the
+     * per-mailbox state, so the effects above start a fresh draft and crypto context in the new mailbox -
+     * the old draft is deleted only once the new one has been created. Recipients, subject, and body are
+     * kept. */
     function handleFromChange(nextMailboxUid: string) {
         if (nextMailboxUid === mailboxUid || hasUploads) {
             return;
         }
         if (draft) {
-            void deleteMessage(draft.uid, draft.version).catch(() => undefined);
+            supersededDraftsRef.current.push(draft);
         }
         setDraft(null);
         setDraftsFolderUid(undefined);
@@ -348,8 +618,14 @@ export default function ComposeWindow({ session, onClose, onToggleMinimize, user
         setFolderError(null);
         setMailbox(null);
         setRecipientStatuses({});
+        discoveryGenerationRef.current += 1;
+        lookupsInFlightRef.current = new Set();
+        lookupFailuresRef.current = new Map();
+        setExhaustedLookups({});
         setEncryptRequested(false);
         setEncryptionBlocked(null);
+        setSecurityBlock(null);
+        offeredCryptoRef.current = { sign: false, encrypt: false };
         setFromMailboxUid(nextMailboxUid);
     }
 
@@ -410,6 +686,7 @@ export default function ComposeWindow({ session, onClose, onToggleMinimize, user
         try {
             const attachment = await uploadAttachment(draft.uid, file);
             setHasUploads(true);
+            void refreshDraftVersion(draft.uid);
             return attachmentContentUrl(attachment.uid);
         } catch (err) {
             setAttachError(err instanceof ApiRequestError ? err.message : "Could not upload image.");
@@ -417,6 +694,18 @@ export default function ComposeWindow({ session, onClose, onToggleMinimize, user
         }
     }
 
+    /** Uploading an attachment bumps the draft's version server-side (it records `hasAttachments`), so a later
+     * Discard would otherwise send a stale `?version=`. Best-effort: Discard also retries with the server's
+     * current version. */
+    async function refreshDraftVersion(uid: string) {
+        try {
+            const fresh = await getMessage(uid);
+            setDraft((prev) => (prev?.uid === fresh.uid && fresh.version > prev.version ? { ...prev, version: fresh.version } : prev));
+        } catch {
+            // Discard's own retry covers a version this couldn't refresh.
+        }
+    }
+
     // The "Attach files" input is itself `disabled` until `draft` resolves (see its `disabled={!draft}`
     // below), so this can only ever fire once `draft` is set — no defensive null check needed, matching
     // this codebase's established pattern for the same class of "always non-null by the time it's
@@ -431,6 +720,7 @@ export default function ComposeWindow({ session, onClose, onToggleMinimize, user
                 const attachment = await uploadAttachment(draft!.uid, file);
                 setHasUploads(true);
                 setAttachments((prev) => [...prev, attachment]);
+                void refreshDraftVersion(draft!.uid);
             } catch (err) {
                 setAttachError(err instanceof ApiRequestError ? err.message : "Could not upload attachment.");
             }
@@ -440,19 +730,24 @@ export default function ComposeWindow({ session, onClose, onToggleMinimize, user
     /**
      * Builds this draft's final body — plaintext, signed-only, or signed+encrypted per
      * `specs/end-to-end_encryption.md` — then stores it via `assembleDraft()`/`assembleDraftRaw()`.
-     * Shared by `handleSend()`/`handleScheduleSend()` (and the "Send without encryption" conflict button
-     * rendered below, via `forcePlaintext`) so the sign/encrypt decision lives in exactly one place.
+     * Shared by immediate and scheduled sends (and the banners' override buttons rendered below, via
+     * `forcePlaintext`) so the sign/encrypt decision lives in exactly one place.
      *
-     * Returns `"blocked"` (never throws for this case) when encryption was requested but not every
-     * recipient can currently be encrypted to — the spec's "Multiple Recipients" all-or-nothing rule.
-     * Sets `encryptionBlocked` as a side effect so the window can render that prompt; callers must stop
-     * (not send) when they get this back.
+     * Returns `"blocked"` (never throws for this case) whenever the message can't go out the way the user
+     * asked for — never a silent downgrade to plaintext:
+     * encryption was requested (or auto-applies) but not every recipient can currently be encrypted to -
+     * the spec's "Multiple Recipients" all-or-nothing rule (sets `encryptionBlocked`); signing/encryption was
+     * on offer this session but the keys have since locked, or the mailbox/encryption policy needed to decide
+     * couldn't be loaded (sets `securityBlock`, and re-prompts the unlock dialog when the keys are merely
+     * locked); or the message would be encrypted but has Bcc recipients - every recipient's certificate goes
+     * into one shared envelope, which would disclose the Bcc list to every other recipient, and the send API
+     * has no per-recipient-copy submission to avoid that (sets `securityBlock`).
+     * Callers must stop (not send) when they get this back. `forcePlaintext` (the user's explicit choice
+     * from one of those banners) skips every one of these checks and never encrypts; signing still
+     * happens if it's currently possible.
      *
      * Discovery (`lookupKeys()`) and the resulting sign/encrypt decision only run at this, the final
-     * pre-send step — not live as recipients are typed. A compose-time recipient-entry indicator (key
-     * icons, live discovery as each address is entered) is Phase 4's "Discovery & contacts UI" work, not
-     * this pass; this still satisfies the spec's "MUST be called lazily at compose time, not on receipt"
-     * requirement, just without a live UI reflecting it before Send is clicked.
+     * pre-send step — `checkRecipientDiscovery()`'s on-blur badges are a best-effort hint only.
      */
     async function assembleForSend(
         toRecipients: ComposeRecipientInput[],
@@ -460,39 +755,93 @@ export default function ComposeWindow({ session, onClose, onToggleMinimize, user
         bccRecipients: ComposeRecipientInput[],
         forcePlaintext: boolean,
     ): Promise<Message | "blocked"> {
+        // Keys are read at the moment they're needed, and again after any await: they can lock (idle
+        // timeout, sign-out elsewhere) mid-send, and a destroyed `UnlockedKeys` object must count as locked.
         // Only reachable once a draft exists, which itself requires `mailboxUid` to have resolved.
-        const unlocked = getUnlockedKeys(mailboxUid!);
-        // `mailbox` is required to build protected headers (own From address) whenever signing or
-        // encrypting - not just guarded on the encryption branch below, since a signed-only message
-        // needs it too. A mailbox fetch failure just means no crypto for this send, never a crash.
-        const canSign = signEnabled && !!mailbox && !!unlocked?.signingPrivateKey && !!unlocked.signingCertDer;
-        const canEncryptSelf = !!unlocked?.encryptionPrivateKey && !!unlocked.encryptionCertDer;
+        function readKeys() {
+            const stored = getUnlockedKeys(mailboxUid!);
+            const unlocked = stored?.destroyed ? undefined : stored;
+            return {
+                unlocked,
+                // `mailbox` is required to build protected headers (own From address) whenever signing or
+                // encrypting - not just guarded on the encryption branch below, since a signed-only message
+                // needs it too.
+                canSign: signEnabled && !!mailbox && !!unlocked?.signingPrivateKey && !!unlocked.signingCertDer,
+                canEncryptSelf: !!unlocked?.encryptionPrivateKey && !!unlocked.encryptionCertDer,
+            };
+        }
+        let keys = readKeys();
         const allRecipients = [...toRecipients, ...ccRecipients, ...bccRecipients];
 
+        // The Sign toggle was shown (and is still checked), but signing can't actually happen any more.
+        const signingLost = () => !forcePlaintext && signEnabled && offeredCryptoRef.current.sign && !keys.canSign;
+        if (signingLost()) {
+            return blockSend(KEYS_LOCKED_SIGN_MESSAGE, "Send without signing or encryption", !keys.unlocked);
+        }
+
+        if (!forcePlaintext && !mailbox) {
+            // The mailbox's enrolled keys are what say whether this message could be encrypted at all - with keys
+            // that aren't unlocked in this session, a failed mailbox load would otherwise skip encryption silently.
+            return blockSend(POLICY_UNAVAILABLE_MESSAGE, "Send without encryption", false);
+        }
+
         let wantEncrypt = false;
         let recipientCertDers: Uint8Array[] = [];
-        if (!forcePlaintext && canEncryptSelf && mailbox && encryptionPolicy && allRecipients.length > 0) {
-            const ownPrefersMutual = mailbox.encryptPreference?.preferEncrypt === "mutual";
-            const lookups = await Promise.all(allRecipients.map((r) => lookupKeys(mailboxUid!, r.address).catch(() => undefined)));
+        // Entered whenever this message could be encrypted at all - including a mailbox with an enrolled
+        // encryption key that this session never unlocked: policy may still auto-encrypt, and that must block
+        // (and prompt to unlock) rather than quietly send plaintext.
+        if (!forcePlaintext && (keys.canEncryptSelf || offeredCryptoRef.current.encrypt || hasEnrolledEncryptionKey)) {
+            if (!encryptionPolicy) {
+                // Without it, there's no telling whether policy auto-encrypts this message.
+                return blockSend(POLICY_UNAVAILABLE_MESSAGE, "Send without encryption", false);
+            }
+            // Reachable only with `mailbox` loaded (checked above).
+            const ownPrefersMutual = mailbox!.encryptPreference?.preferEncrypt === "mutual";
+            const lookups = await Promise.all(
+                allRecipients.map((r) =>
+                    lookupKeys(mailboxUid!, r.address).then(
+                        (lookup) => ({ lookup }),
+                        () => null,
+                    ),
+                ),
+            );
+            keys = readKeys();
+            if (signingLost()) {
+                return blockSend(KEYS_LOCKED_SIGN_MESSAGE, "Send without signing or encryption", !keys.unlocked);
+            }
+            // A failed lookup isn't "no key": treating it as one could send plaintext that policy would encrypt.
+            if (lookups.some((result) => !result) && (encryptRequested || policyCanAutoEncrypt(encryptionPolicy))) {
+                return blockSend(LOOKUP_UNAVAILABLE_MESSAGE, "Send without encryption", false);
+            }
             const statuses = allRecipients.map((r, i) =>
-                resolveRecipientEncryption(mailbox.primarySmtpAddress, ownPrefersMutual, encryptionPolicy, r.address, lookups[i]),
+                resolveRecipientEncryption(mailbox!.primarySmtpAddress, ownPrefersMutual, encryptionPolicy, r.address, lookups[i]?.lookup),
             );
             const decision = decideMessageEncryption(statuses);
             wantEncrypt = encryptRequested || decision.autoEncrypt;
             if (wantEncrypt) {
+                if (!keys.canEncryptSelf) {
+                    return blockSend(KEYS_LOCKED_ENCRYPT_MESSAGE, "Send without encryption", !keys.unlocked);
+                }
                 if (!decision.canEncryptAll) {
                     setEncryptionBlocked(decision.blockedRecipients);
                     return "blocked";
                 }
-                recipientCertDers = [unlocked!.encryptionCertDer!, ...statuses.map((s) => fromBase64(s.encryptCert!.publicKey))];
+                if (bccRecipients.length > 0) {
+                    return blockSend(BCC_ENCRYPTED_MESSAGE, "Send without encryption", false);
+                }
+                recipientCertDers = [keys.unlocked!.encryptionCertDer!, ...statuses.map((s) => fromBase64(s.encryptCert!.publicKey))];
             }
         }
 
+        const { canSign } = keys;
         if ((wantEncrypt || canSign) && attachments.length > 0) {
             // Matches BaseMailComposeRoute.assembleRaw()'s own server-side rejection, surfaced here with a
             // clearer explanation than that route's generic 400 rather than via a round trip.
             throw new ApiRequestError("A signed or encrypted message cannot include file attachments yet - remove them before sending.", 400);
         }
+        if ((wantEncrypt || canSign) && INLINE_IMAGE_PATTERN.test(html)) {
+            throw new ApiRequestError("A signed or encrypted message cannot include inline images yet - remove them before sending.", 400);
+        }
 
         if (!wantEncrypt && !canSign) {
             // See the old compose page's identical note: `sanitize-html` is Node-oriented and the server-side
@@ -502,9 +851,10 @@ export default function ComposeWindow({ session, onClose, onToggleMinimize, user
         }
 
         const domain = mailbox!.primarySmtpAddress.split("@")[1] ?? "localhost";
+        const displayName = mailbox!.displayName && !UNSAFE_DISPLAY_NAME_PATTERN.test(mailbox!.displayName) ? mailbox!.displayName : "";
         const protectedHeaders: ProtectedHeaders = {
-            from: mailbox!.displayName
-                ? `"${mailbox!.displayName.replace(/"/g, '\\"')}" <${mailbox!.primarySmtpAddress}>`
+            from: displayName
+                ? `"${displayName.replace(/"/g, '\\"')}" <${mailbox!.primarySmtpAddress}>`
                 : mailbox!.primarySmtpAddress,
             to: toRecipients.map((r) => r.address).join(", "),
             cc: ccRecipients.length > 0 ? ccRecipients.map((r) => r.address).join(", ") : undefined,
@@ -513,7 +863,7 @@ export default function ComposeWindow({ session, onClose, onToggleMinimize, user
             messageId: `<${crypto.randomUUID()}@${domain}>`,
         };
         const bodyContentType = 'text/html; charset="utf-8"';
-        const signing = canSign ? { certDer: unlocked!.signingCertDer!, privateKey: unlocked!.signingPrivateKey! } : undefined;
+        const signing = canSign ? { certDer: keys.unlocked!.signingCertDer!, privateKey: keys.unlocked!.signingPrivateKey! } : undefined;
 
         const outerHeaders = wantEncrypt ? applyBaselineOuterHeaders(protectedHeaders) : protectedHeaders;
         const mimePart = wantEncrypt
@@ -523,9 +873,26 @@ export default function ComposeWindow({ session, onClose, onToggleMinimize, user
         return assembleDraftRaw(draft!.uid, { to: toRecipients, cc: ccRecipients, bcc: bccRecipients, subject: outerHeaders.subject, rawMime });
     }
 
-    // Same reasoning as `handleFilesSelected` above: the Send button is itself `disabled` until `draft`
-    // resolves, so this is never reachable with a null `draft`.
-    async function handleSend(forcePlaintext = false) {
+    /** Records why a send was refused (see `assembleForSend()`), re-prompting the unlock dialog when the
+     * cause is keys that are enrolled but locked. */
+    function blockSend(message: string, overrideLabel: string, keysLocked: boolean): "blocked" {
+        setSecurityBlock({ message, overrideLabel });
+        if (keysLocked && (hasEnrolledSigningKey || hasEnrolledEncryptionKey)) {
+            void handleUnlockForCrypto();
+        }
+        return "blocked";
+    }
+
+    /**
+     * Sends (or, given `scheduledSendTimeIso`, schedules) the draft. Same reasoning as `handleFilesSelected`
+     * above: Send and the "Send later" caret are both `disabled` until `draft` resolves, so this is never
+     * reachable with a null `draft`. A scheduled send assembles the draft first (same as an immediate send),
+     * then sets `scheduledSendTime` on the *freshly assembled* copy before calling `sendMessage()` — `send()`
+     * itself is what reads the field and defers relay into Outbox instead of sending immediately (see
+     * `mailApi.ts`'s own doc comment on `setMessageScheduledSendTime`). A blocked send remembers its schedule
+     * time so the banners' override buttons replay it as the same kind of send.
+     */
+    async function submit(forcePlaintext: boolean, scheduledSendTimeIso?: string) {
         const toRecipients = parseAddresses(to);
         if (toRecipients.length === 0) {
             setSendError("At least one recipient is required.");
@@ -533,63 +900,247 @@ export default function ComposeWindow({ session, onClose, onToggleMinimize, user
         }
 
         setSending(true);
+        sendingRef.current = true;
         setSendError(null);
+        setSecurityBlock(null);
+        setEncryptionBlocked(null);
+        pendingSaveRef.current = false;
         try {
+            // An autosave already on the wire must never land after (and overwrite) the send's own assembly.
+            await saveInFlightRef.current;
             const assembled = await assembleForSend(toRecipients, parseAddresses(cc), parseAddresses(bcc), forcePlaintext);
             if (assembled === "blocked") {
+                setBlockedScheduleIso(scheduledSendTimeIso);
                 return;
             }
+            // The draft now holds exactly this content (possibly signed/encrypted) - don't autosave a
+            // plaintext copy over it if the rest of the send fails.
+            lastSavedRef.current = `${assembled.uid}:${contentKey}`;
             const withReceipt = requestReceipt ? await setMessageRequestReceipt(assembled, true) : assembled;
-            await sendMessage(withReceipt.uid);
+            await sendMessage(withReceipt.uid, scheduledSendTimeIso ? { scheduledSendTime: scheduledSendTimeIso } : undefined);
+            finishedRef.current = true;
             onClose();
         } catch (err) {
-            setSendError(err instanceof ApiRequestError ? err.message : "Could not send this message.");
+            const fallback = scheduledSendTimeIso ? "Could not schedule this message." : "Could not send this message.";
+            setSendError(err instanceof ApiRequestError ? err.message : fallback);
         } finally {
+            sendingRef.current = false;
             setSending(false);
         }
     }
 
-    // Same reasoning as `handleSend` above (and the "Send later" caret is itself `disabled` alongside
-    // Send until `draft` resolves) — never reachable with a null `draft`. Assembles the draft first
-    // (same as an immediate send), then sets `scheduledSendTime` on the *freshly assembled* copy before
-    // calling `sendMessage()` — `send()` itself is what reads the field and defers relay into Outbox
-    // instead of sending immediately (see `mailApi.ts`'s own doc comment on `setMessageScheduledSendTime`).
-    async function handleScheduleSend(scheduledSendTimeIso: string) {
-        const toRecipients = parseAddresses(to);
+    function handleScheduleSend(scheduledSendTimeIso: string) {
         setSchedulePickerOpen(false);
-        if (toRecipients.length === 0) {
-            setSendError("At least one recipient is required.");
-            return;
+        void submit(false, scheduledSendTimeIso);
+    }
+
+    async function handleUnlockForCrypto() {
+        try {
+            // Only reachable when hasEnrolledSigningKey/hasEnrolledEncryptionKey found a real enrolled key
+            // in mailbox.keys (the unlock button below, or blockSend()), so neither is empty/undefined here.
+            await requestUnlock(mailbox!.uid, mailbox!.keys!);
+            setUnlockRefresh((n) => n + 1);
+        } catch {
+            // User dismissed the unlock dialog - nothing to do, the toggles below simply stay hidden.
         }
+    }
 
-        setSending(true);
-        setSendError(null);
+    /**
+     * Saves the window's current recipients/subject/body onto its server draft via `assembleDraft()` (the
+     * same plaintext assembly a normal send uses). Chained after any save already on the wire - two
+     * overlapping assemblies of the same draft race on its version and the later one is rejected - and reads
+     * `latestRef` only once it actually runs, so it saves what was last typed (skipping the request when the
+     * save before it already stored exactly that). Whether a save may happen at all is re-checked at that same
+     * moment: while it waited, the message may have become one that must not be stored as plaintext (Encrypt
+     * turned on, a recipient that auto-encrypts), or the window may have started sending or finished - then it
+     * resolves `{ skipped: true }` without a request (`message` then being the previous save's result). Never
+     * rejects; `message` is `undefined` when the save failed.
+     */
+    function saveDraftNow(): Promise<{ message?: Message; skipped?: boolean }> {
+        const target = latestRef.current.draft!;
+        const previous = saveInFlightRef.current;
+        pendingSaveRef.current = false;
+        setSaveStatus("saving");
+        const outcome = (async (): Promise<{ message?: Message; skipped?: boolean }> => {
+            const before = await previous;
+            const current = latestRef.current;
+            if (current.autosaveSuppressed || sendingRef.current || finishedRef.current) {
+                setSaveStatus("idle");
+                // Still the newest copy the server holds, for the version a later delete needs.
+                return { skipped: true, message: before };
+            }
+            const savedKey = `${target.uid}:${current.contentKey}`;
+            if (before?.uid === target.uid && lastSavedRef.current === savedKey) {
+                setSaveStatus("saved");
+                return { message: before };
+            }
+            try {
+                const saved = await assembleDraft(target.uid, {
+                    to: parseAddresses(current.to),
+                    cc: parseAddresses(current.cc),
+                    bcc: parseAddresses(current.bcc),
+                    subject: current.subject,
+                    html: current.html,
+                });
+                lastSavedRef.current = savedKey;
+                saveErrorRef.current = null;
+                // A From switch may have replaced the draft while this was in flight - never resurrect it,
+                // but do keep its superseded copy's version current so its pending delete still matches.
+                setDraft((prev) => (prev?.uid === saved.uid ? saved : prev));
+                const superseded = supersededDraftsRef.current.find((d) => d.uid === saved.uid);
+                if (superseded) {
+                    superseded.version = saved.version;
+                }
+                setSaveStatus("saved");
+                return { message: saved };
+            } catch (err) {
+                saveErrorRef.current = err instanceof ApiRequestError ? err.message : "the server couldn't be reached";
+                setSaveStatus("error");
+                return {};
+            }
+        })();
+        saveInFlightRef.current = outcome.then((result) => result.message);
+        return outcome;
+    }
+
+    /** Keeps the window open after its content couldn't be saved, offering Discard or Keep editing. */
+    function showSaveFailedPrompt() {
+        setClosePrompt({
+            title: "Couldn't save this draft",
+            message: `It couldn't be saved (${saveErrorRef.current!.replace(/\.$/, "")}). Keep editing and try again, or discard it.`,
+        });
+    }
+
+    /**
+     * Deletes `current` (this window's server draft) once any save already on the wire has landed, so the delete
+     * carries the draft's current version. A delete rejected for a stale version (404/409: e.g. an attachment
+     * upload bumped it) is retried once with the version the server holds - and a draft the server no longer has
+     * counts as deleted. The retry only happens while the server copy is still an unsent draft in the same folder.
+     * Rejects when the draft couldn't be deleted.
+     */
+    async function deleteDraft(current: Message): Promise<void> {
+        const saved = await saveInFlightRef.current;
+        const version = Math.max(current.version, saved?.uid === current.uid ? saved.version : 0);
         try {
-            const assembled = await assembleForSend(toRecipients, parseAddresses(cc), parseAddresses(bcc), false);
-            if (assembled === "blocked") {
+            await deleteMessage(current.uid, version);
+        } catch (err) {
+            if (!(err instanceof ApiRequestError) || (err.status !== 404 && err.status !== 409)) {
+                throw err;
+            }
+            const fresh = await getMessage(current.uid).catch((getErr: unknown) => {
+                if (getErr instanceof ApiRequestError && getErr.status === 404) {
+                    return null;
+                }
+                throw getErr;
+            });
+            if (!fresh) {
                 return;
             }
-            const withReceipt = requestReceipt ? await setMessageRequestReceipt(assembled, true) : assembled;
-            const scheduled = await setMessageScheduledSendTime(withReceipt, scheduledSendTimeIso);
-            await sendMessage(scheduled.uid);
+            // The version changed because another window sent or scheduled it - that message isn't ours to delete.
+            if (!isStillDraft(fresh, current.folderUid)) {
+                throw new ApiRequestError(NO_LONGER_A_DRAFT_MESSAGE, 409);
+            }
+            await deleteMessage(fresh.uid, fresh.version);
+        }
+    }
+
+    /**
+     * Discards the window's draft and closes it. With nothing the user would lose (a blank draft) it closes
+     * straight away and deletes the draft in the background; otherwise it closes only once the draft is
+     * deleted, and a delete that fails keeps the window open with the error.
+     */
+    async function discardNow() {
+        finishedRef.current = true;
+        pendingSaveRef.current = false;
+        setClosePrompt(null);
+        setDiscardError(null);
+        const current = draft;
+        if (!current || !hasUserContent) {
+            if (current) {
+                void deleteDraft(current).catch(() => undefined);
+            }
             onClose();
+            return;
+        }
+        setClosing(true);
+        try {
+            await deleteDraft(current);
         } catch (err) {
-            setSendError(err instanceof ApiRequestError ? err.message : "Could not schedule this message.");
-        } finally {
-            setSending(false);
+            finishedRef.current = false;
+            setClosing(false);
+            setDiscardError(`Couldn't discard this draft: ${err instanceof ApiRequestError ? err.message : "the server couldn't be reached."}`);
+            return;
         }
+        onClose();
     }
 
-    async function handleUnlockForCrypto() {
-        try {
-            // Only reachable via the button below, which never renders unless needsUnlockForCrypto is
-            // true - which itself requires mailbox.keys to already contain a real enrolled key (see
-            // hasEnrolledSigningKey/hasEnrolledEncryptionKey), so it's never empty/undefined here either.
-            await requestUnlock(mailbox!.uid, mailbox!.keys!);
-            setUnlockRefresh((n) => n + 1);
-        } catch {
-            // User dismissed the unlock dialog - nothing to do, the toggles below simply stay hidden.
+    /** "Discard draft": confirms first whenever there's anything the user would lose. */
+    function handleDiscard() {
+        if (hasUserContent) {
+            setClosePrompt({ title: DISCARD_TITLE, message: "This permanently deletes this draft and everything you've written in it." });
+        } else {
+            void discardNow();
+        }
+    }
+
+    /** "Close": keeps the draft (saving any unsaved edits first, and closing only once that save succeeded) -
+     * unless there's nothing in it worth keeping, or it can't be saved because it's headed for encryption, or
+     * whether it is can't be told yet (settings loading or unavailable, recipient lookups pending): those need
+     * the same confirmation as a discard. A failed save keeps the window open with Discard / Keep editing.
+     * Close and Discard are both disabled while a send is in progress: deleting the draft, or saving a
+     * plaintext copy over the message the send just assembled, mid-send would lose or leak it. */
+    async function handleClose() {
+        if (!hasUserContent) {
+            void discardNow();
+            return;
+        }
+        if (encryptionDecided) {
+            setClosePrompt({ title: DISCARD_TITLE, message: ENCRYPTED_CLOSE_MESSAGE });
+            return;
+        }
+        if (cryptoCheckUnavailable) {
+            setClosePrompt({ title: DISCARD_TITLE, message: CRYPTO_UNAVAILABLE_MESSAGE, retry: true });
+            return;
+        }
+        if (awaitingRecipients) {
+            setClosePrompt({ title: DISCARD_TITLE, message: NO_RECIPIENTS_CLOSE_MESSAGE });
+            return;
+        }
+        if (encryptionUndetermined) {
+            // A recipient typed but never blurred has no lookup running yet.
+            checkRecipientDiscovery([...parseAddresses(to), ...parseAddresses(cc), ...parseAddresses(bcc)]);
+            setClosePrompt({ title: DISCARD_TITLE, message: CHECKING_CLOSE_MESSAGE });
+            return;
+        }
+        if (!draft || !contentReady) {
+            saveErrorRef.current = draftError ?? "the draft hasn't been created yet";
+            showSaveFailedPrompt();
+            return;
+        }
+        if (lastSavedRef.current !== `${draft.uid}:${contentKey}`) {
+            setClosing(true);
+            const outcome = await saveDraftNow();
+            setClosing(false);
+            if (outcome.skipped) {
+                // It became a message that mustn't be saved as plaintext while waiting on an earlier save.
+                setClosePrompt({ title: DISCARD_TITLE, message: latestRef.current.encryptionDecided ? ENCRYPTED_CLOSE_MESSAGE : CHECKING_CLOSE_MESSAGE });
+                return;
+            }
+            if (!outcome.message) {
+                showSaveFailedPrompt();
+                return;
+            }
         }
+        finishedRef.current = true;
+        onClose();
+    }
+
+    function retryCryptoContext() {
+        setClosePrompt(null);
+        setCryptoRetryToken((n) => n + 1);
+        lookupFailuresRef.current = new Map();
+        setExhaustedLookups({});
+        setLookupRetryToken((n) => n + 1);
     }
 
     // A plain read from keySession.ts's module-level session store, not React state - see that module's
@@ -601,15 +1152,163 @@ export default function ComposeWindow({ session, onClose, onToggleMinimize, user
     // the sign/encrypt toggles below stay hidden until it has, so this is the only way to reach them
     // without first stumbling into Mail generally (which no longer force-prompts on its own - see
     // `MailShell`'s `blocking={false}`). `getUnlockedKeys()` is re-read as a plain module value above, so
-    // bumping `unlockRefresh` after a successful unlock is what makes this line (and the toggles it
-    // gates) reflect it on the next render.
+    // bumping `unlockRefresh` (after a successful unlock, or on any key-session event for this mailbox -
+    // see the `subscribeKeySession()` effect) is what makes this line (and the toggles it gates) reflect
+    // it on the next render.
     const needsUnlockForCrypto = (hasEnrolledSigningKey || hasEnrolledEncryptionKey) && !unlockedKeys;
 
+    // Keys locking (idle timeout, logout elsewhere, ...) or unlocking from another window must update the
+    // toggles/unlock affordance right away, not on whatever unrelated render happens next.
+    useEffect(() => subscribeKeySession((event) => {
+        if (event.mailboxUid === mailboxUid) {
+            setUnlockRefresh((n) => n + 1);
+        }
+    }), [mailboxUid]);
+
+    useEffect(() => {
+        offeredCryptoRef.current = {
+            sign: offeredCryptoRef.current.sign || !!unlockedKeys?.signingPrivateKey,
+            encrypt: offeredCryptoRef.current.encrypt || !!unlockedKeys?.encryptionPrivateKey,
+        };
+    });
+
+    // Autosave. "User content" is anything beyond what compose opened with (prefilled recipients/subject,
+    // seeded signature/quote) - an untouched window has nothing worth saving or confirming a discard of.
+    const contentKey = JSON.stringify([to, cc, bcc, subject, html]);
+    const baselineKey = JSON.stringify([initialTo ?? "", initialCc ?? "", "", initialSubject ?? "", seededHtml ?? ""]);
+    const hasUserContent = contentKey !== baselineKey || hasUploads;
+    // A message headed for encryption is never autosaved: the draft would store its plaintext server-side,
+    // defeating end-to-end encryption. Until it's known not to be, it isn't either: while the mailbox (whose
+    // enrolled keys say whether encryption is possible at all) or the encryption policy hasn't loaded, and -
+    // whenever this message could be encrypted (an unlocked or enrolled encryption key) - while the policy is
+    // missing or any current recipient's lookup is still pending (or failed, or hasn't run) - and while there are no
+    // recipients at all when policy auto-encrypts some tier, since the first one added may turn encryption on.
+    const currentAddresses = [...parseAddresses(to), ...parseAddresses(cc), ...parseAddresses(bcc)].map((r) => r.address);
+    const currentStatuses = currentAddresses.map((address) => recipientStatuses[address]);
+    const encryptionPossible = !!unlockedKeys?.encryptionPrivateKey || hasEnrolledEncryptionKey || offeredCryptoRef.current.encrypt;
+    /** Could be auto-encrypted, but has no recipients yet to decide by. */
+    const awaitingRecipients = encryptionPossible && !!encryptionPolicy && currentAddresses.length === 0 && policyCanAutoEncrypt(encryptionPolicy);
+    const encryptionUndetermined =
+        !cryptoContextReady || !mailbox || awaitingRecipients || (encryptionPossible && (!encryptionPolicy || currentStatuses.some((s) => !s)));
+    /** Known to be headed for encryption: requested, or policy auto-encrypts it. */
+    const encryptionDecided = encryptRequested || (!encryptionUndetermined && encryptionPossible && decideMessageEncryption(currentStatuses).autoEncrypt);
+    const autosaveSuppressed = encryptionDecided || encryptionUndetermined;
+    /** Loading the mailbox/policy failed (retries may still be pending) and this message's encryption hinges on it, or
+     * a current recipient's key lookup kept failing. */
+    const cryptoCheckUnavailable =
+        (cryptoContextReady && cryptoLoadFailed && (!mailbox || (encryptionPossible && !encryptionPolicy))) ||
+        (encryptionPossible && currentAddresses.some((address) => exhaustedLookups[address] && !recipientStatuses[address]));
+    const latestRef = useRef({ draft, to, cc, bcc, subject, html, contentKey, saveStatus, hasUserContent, autosaveSuppressed, encryptionDecided });
+    latestRef.current = { draft, to, cc, bcc, subject, html, contentKey, saveStatus, hasUserContent, autosaveSuppressed, encryptionDecided };
+
+    useEffect(() => {
+        const due =
+            !!draft &&
+            contentReady &&
+            cryptoContextReady &&
+            !sending &&
+            !autosaveSuppressed &&
+            hasUserContent &&
+            lastSavedRef.current !== `${draft.uid}:${contentKey}`;
+        pendingSaveRef.current = due;
+        if (!due) {
+            return;
+        }
+        const timer = setTimeout(() => void saveDraftNow(), autosaveDelayMs);
+        return () => clearTimeout(timer);
+    }, [draft, contentReady, cryptoContextReady, sending, autosaveSuppressed, hasUserContent, contentKey]);
+
+    // Unmounting with an edit still waiting on the debounce (e.g. the whole app shell unmounting) saves it
+    // right away rather than losing it.
+    useEffect(
+        () => () => {
+            if (pendingSaveRef.current && !finishedRef.current) {
+                void saveDraftNow();
+            }
+        },
+        [],
+    );
+
+    /** Saves an edit still waiting on the debounce now, and resolves once that save - or one already on the
+     * wire - has settled, to whether the window's content is saved. A save that failed keeps the window open
+     * with Discard / Keep editing. A send clears `pendingSaveRef` before it starts, so this never saves mid-send. */
+    async function flushPendingSave(): Promise<boolean> {
+        if (pendingSaveRef.current && !finishedRef.current) {
+            const outcome = await saveDraftNow();
+            if (outcome.skipped) {
+                // Not saved, but not a failure either: it may be headed for encryption (or was sent/discarded meanwhile).
+                return finishedRef.current;
+            }
+            if (!outcome.message) {
+                showSaveFailedPrompt();
+            }
+            return !!outcome.message;
+        }
+        await saveInFlightRef.current;
+        const latest = latestRef.current;
+        if (finishedRef.current || !latest.hasUserContent || (!!latest.draft && lastSavedRef.current === `${latest.draft.uid}:${latest.contentKey}`)) {
+            return true;
+        }
+        // Unsaved because the last save failed (rather than, say, an encrypted message never being saved).
+        if (saveErrorRef.current) {
+            showSaveFailedPrompt();
+        }
+        return false;
+    }
+
+    // Sign Out (AppShell) waits for this before ending the session.
+    useEffect(() => registerComposeFlush(flushPendingSave), []);
+
+    // Leaving the page (reload, closing the tab, following a link) with anything not saved: start a save that's
+    // waiting on the debounce straight away and ask the browser to confirm, so the last couple of seconds of
+    // typing (or content that can't be saved as a draft, or failed to) aren't lost silently. Never while signing
+    // out - that navigation must not be cancellable.
+    useEffect(() => {
+        function handleBeforeUnload(event: BeforeUnloadEvent) {
+            if (finishedRef.current || sendingRef.current || isSigningOut()) {
+                return;
+            }
+            const latest = latestRef.current;
+            const unsaved =
+                pendingSaveRef.current ||
+                latest.saveStatus === "saving" ||
+                (latest.hasUserContent && lastSavedRef.current !== `${latest.draft?.uid}:${latest.contentKey}`);
+            if (!unsaved) {
+                return;
+            }
+            void flushPendingSave();
+            event.preventDefault();
+            event.returnValue = "";
+        }
+        window.addEventListener("beforeunload", handleBeforeUnload);
+        return () => window.removeEventListener("beforeunload", handleBeforeUnload);
+    }, []);
+
     const title = subject.trim() || "New Message";
     const titleId = `compose-title-${id}`;
 
+    const discardModal = (
+        <Modal open={closePrompt !== null} onClose={() => setClosePrompt(null)} title={closePrompt?.title ?? DISCARD_TITLE}>
+            <p className="text-sm text-text-muted mb-4">{closePrompt?.message}</p>
+            <div className="flex gap-3">
+                {closePrompt?.retry && (
+                    <Button type="button" onClick={retryCryptoContext} className="!w-auto">
+                        Retry
+                    </Button>
+                )}
+                <Button type="button" onClick={() => void discardNow()} disabled={sending || closing} className="!w-auto">
+                    Discard
+                </Button>
+                <Button type="button" variant="secondary" onClick={() => setClosePrompt(null)} className="!w-auto">
+                    Keep editing
+                </Button>
+            </div>
+        </Modal>
+    );
+
     if (minimized) {
         return (
+            <>
             <div role="dialog" aria-label={title} className="w-64 shrink-0 bg-surface border border-border border-b-0 rounded-t-md shadow-modal">
                 <div
                     className="h-10 flex items-center justify-between gap-2 px-3 rounded-t-md bg-primary-darker text-white cursor-pointer"
@@ -618,18 +1317,17 @@ export default function ComposeWindow({ session, onClose, onToggleMinimize, user
                     <span className="text-sm font-medium truncate">{title}</span>
                     <div className="flex items-center gap-0.5" onClick={(e) => e.stopPropagation()}>
                         <HeaderButton label="Restore" onClick={onToggleMinimize} icon={HiOutlineArrowsPointingOut} />
-                        <HeaderButton
-                            label="Discard draft"
-                            onClick={onClose}
-                            icon={HiOutlineXMark}
-                        />
+                        <HeaderButton label="Discard draft" onClick={handleDiscard} icon={HiOutlineXMark} disabled={sending || closing} />
                     </div>
                 </div>
             </div>
+            {discardModal}
+            </>
         );
     }
 
     return (
+        <>
         <div
             ref={windowRef}
             role="dialog"
@@ -679,17 +1377,29 @@ export default function ComposeWindow({ session, onClose, onToggleMinimize, user
                             icon={expanded ? HiOutlineArrowsPointingIn : HiOutlineArrowsPointingOut}
                         />
                     )}
-                    <HeaderButton label="Close" onClick={onClose} icon={HiOutlineXMark} />
+                    <HeaderButton label="Close" onClick={() => void handleClose()} icon={HiOutlineXMark} disabled={sending || closing} />
                 </div>
             </div>
 
             <div className="flex-1 min-h-0 flex flex-col">
-                {(folderError || draftError || sendError || attachError) && (
+                {(folderError || draftError || sendError || attachError || discardError) && (
                     <div className="px-3 pt-2">
                         {folderError && <Alert>{folderError}</Alert>}
                         {draftError && <Alert>{draftError}</Alert>}
                         {sendError && <Alert>{sendError}</Alert>}
                         {attachError && <Alert>{attachError}</Alert>}
+                        {discardError && <Alert>{discardError}</Alert>}
+                    </div>
+                )}
+
+                {cryptoCheckUnavailable && (
+                    <div className="px-3 pt-2">
+                        <Alert>
+                            <p className="mb-2">{CRYPTO_UNAVAILABLE_MESSAGE}</p>
+                            <Button type="button" variant="secondary" className="!w-auto" onClick={retryCryptoContext}>
+                                Retry
+                            </Button>
+                        </Alert>
                     </div>
                 )}
 
@@ -702,20 +1412,25 @@ export default function ComposeWindow({ session, onClose, onToggleMinimize, user
                                 Remove {encryptionBlocked.length > 1 ? "these recipients" : "this recipient"} from To/Cc/Bcc, or send the
                                 whole message in plaintext.
                             </p>
-                            <Button
-                                type="button"
-                                onClick={() => {
-                                    setEncryptionBlocked(null);
-                                    void handleSend(true);
-                                }}
-                            >
+                            <Button type="button" disabled={sending} onClick={() => void submit(true, blockedScheduleIso)}>
                                 Send without encryption
                             </Button>
                         </Alert>
                     </div>
                 )}
 
-                {mailboxes.length > 1 && (
+                {securityBlock && (
+                    <div className="px-3 pt-2">
+                        <Alert>
+                            <p className="mb-2">{securityBlock.message}</p>
+                            <Button type="button" disabled={sending} onClick={() => void submit(true, blockedScheduleIso)}>
+                                {securityBlock.overrideLabel}
+                            </Button>
+                        </Alert>
+                    </div>
+                )}
+
+                {fromOptions.length > 1 && (
                     <div className={FIELD_ROW}>
                         <label htmlFor={`compose-from-${id}`} className="text-xs text-text-muted shrink-0">
                             From
@@ -728,7 +1443,7 @@ export default function ComposeWindow({ session, onClose, onToggleMinimize, user
                             title={hasUploads ? "The sender can't be changed after adding attachments or images." : undefined}
                             onChange={(e) => handleFromChange(e.target.value)}
                         >
-                            {mailboxes.map((mb) => (
+                            {fromOptions.map((mb) => (
                                 <option key={mb.uid} value={mb.uid}>
                                     {mb.displayName ? `${mb.displayName} <${mb.primarySmtpAddress}>` : mb.primarySmtpAddress}
                                     {mb.ownerUserUid ? "" : " (shared)"}
@@ -878,8 +1593,8 @@ export default function ComposeWindow({ session, onClose, onToggleMinimize, user
                     <div className="flex items-center rounded-pill bg-primary text-white overflow-hidden">
                         <button
                             type="button"
-                            onClick={() => handleSend()}
-                            disabled={!draft || sending || !cryptoContextReady}
+                            onClick={() => void submit(false)}
+                            disabled={!draft || sending || closing || !cryptoContextReady}
                             className="py-1.5 pl-5 pr-3 font-semibold text-sm hover:not-disabled:bg-primary-dark disabled:opacity-55 disabled:cursor-not-allowed"
                         >
                             {sending ? "Sending…" : "Send"}
@@ -890,7 +1605,7 @@ export default function ComposeWindow({ session, onClose, onToggleMinimize, user
                             aria-label="Send later"
                             aria-haspopup="true"
                             aria-expanded={schedulePickerOpen}
-                            disabled={!draft || sending || !cryptoContextReady}
+                            disabled={!draft || sending || closing || !cryptoContextReady}
                             onClick={() => setSchedulePickerOpen((o) => !o)}
                             className="py-1.5 px-2 border-l border-white/30 hover:not-disabled:bg-primary-dark disabled:opacity-55 disabled:cursor-not-allowed"
                         >
@@ -914,17 +1629,24 @@ export default function ComposeWindow({ session, onClose, onToggleMinimize, user
                         <input type="file" multiple disabled={!draft} onChange={handleFilesSelected} className="sr-only" />
                     </label>
 
+                    <span role="status" aria-live="polite" className="ml-auto text-xs text-text-muted">
+                        {SAVE_STATUS_LABEL[saveStatus]}
+                    </span>
+
                     <button
                         type="button"
                         aria-label="Discard draft"
                         title="Discard draft"
-                        onClick={onClose}
-                        className="ml-auto w-8 h-8 flex items-center justify-center rounded-full text-text-muted hover:bg-surface-alt hover:text-text"
+                        onClick={handleDiscard}
+                        disabled={sending || closing}
+                        className="w-8 h-8 flex items-center justify-center rounded-full text-text-muted hover:bg-surface-alt hover:text-text disabled:opacity-40 disabled:cursor-not-allowed"
                     >
                         <HiOutlineTrash size={18} />
                     </button>
                 </div>
             </div>
         </div>
+        {discardModal}
+        </>
     );
 }