From 9f230ca8fcbbde11eec25031b5b695230dc389eb Mon Sep 17 00:00:00 2001
From: Linus Rath <139418639+rathlinus@users.noreply.github.com>
Date: Wed, 28 Oct 2026 05:23:25 +0100
Subject: [PATCH] fix: keep a quick reply as a draft when an automatic sign-out
 comes while the external recipient question is open

---
 .../viewer-quick-reply-back.test.tsx          | 28 +++++++++++++++++++
 components/email/email-viewer.tsx             | 12 ++++++--
 2 files changed, 38 insertions(+), 2 deletions(-)

diff --git a/components/email/__tests__/viewer-quick-reply-back.test.tsx b/components/email/__tests__/viewer-quick-reply-back.test.tsx
index c9f478d82..39fae9a39 100644
--- a/components/email/__tests__/viewer-quick-reply-back.test.tsx
+++ b/components/email/__tests__/viewer-quick-reply-back.test.tsx
@@ -62,3 +62,31 @@ describe('quick reply', () => {
     expect(box.value).toBe('');
   });
 });
+
+describe('automatic sign-out while the external recipient question is open', () => {
+  it('answers Back and keeps the typed reply as a draft, without asking again', async () => {
+    const { useExternalRecipientConfirmStore } = await import('@/stores/external-recipient-confirm-store');
+    const { flushComposers, resetComposeFlushRegistry } = await import('@/lib/compose-flush-registry');
+    resetComposeFlushRegistry();
+    useExternalRecipientConfirmStore.setState({ pending: null, queue: [] });
+    const onQuickReply = vi.fn((body: string) => {
+      void body;
+      return useExternalRecipientConfirmStore.getState().ask([{ address: 'org-dave@org-two.test', domain: 'org-two.test', field: 'to' }]);
+    });
+    const onSaveQuickReplyDraft = vi.fn(async () => {});
+    render(<EmailViewer email={message} isLoading={false} mailboxes={mailboxes} selectedMailbox="inbox" currentMailboxRole="inbox"
+      onQuickReply={onQuickReply} onSaveQuickReplyDraft={onSaveQuickReplyDraft} />);
+    await act(async () => { await new Promise((r) => setTimeout(r, 10)); });
+    const box = screen.getByPlaceholderText('quick_reply_placeholder') as HTMLTextAreaElement;
+    fireEvent.focus(box);
+    fireEvent.change(box, { target: { value: 'My answer' } });
+    fireEvent.click(screen.getByRole('button', { name: 'send' }));
+    await waitFor(() => expect(useExternalRecipientConfirmStore.getState().pending).not.toBeNull());
+
+    await act(async () => { await flushComposers(2000); });
+    expect(onSaveQuickReplyDraft).toHaveBeenCalledWith('My answer');
+    expect(useExternalRecipientConfirmStore.getState().pending).toBeNull();
+    expect(box.value).toBe('My answer');
+    expect(onQuickReply).toHaveBeenCalledTimes(1);
+  });
+});
diff --git a/components/email/email-viewer.tsx b/components/email/email-viewer.tsx
index bac5a0b13..d0f6099ab 100644
--- a/components/email/email-viewer.tsx
+++ b/components/email/email-viewer.tsx
@@ -103,6 +103,7 @@ import { useSettingsStore } from "@/stores/settings-store";
 import { useShallow } from "zustand/react/shallow";
 import { useEffectiveMailLayout } from "@/hooks/use-effective-mail-layout";
 import { registerComposeFlush } from "@/lib/compose-flush-registry";
+import { useExternalRecipientConfirmStore } from "@/stores/external-recipient-confirm-store";
 import { useUIStore } from "@/stores/ui-store";
 import { useContactStore, getContactDisplayName, getContactPrimaryEmail } from "@/stores/contact-store";
 import { toast } from "@/stores/toast-store";
@@ -1377,7 +1378,9 @@ export function EmailViewer({
   const [isQuickReplyFocused, setIsQuickReplyFocused] = useState(false);
   const [isSendingQuickReply, setIsSendingQuickReply] = useState(false);
   // An automatic sign-out keeps typed quick-reply text as a draft; text on
-  // its way out as a reply needs none.
+  // its way out as a reply needs none. A reply still waiting on the
+  // "Send outside your organisation?" question hasn't gone out: the question
+  // is answered with Back and the text kept as a draft.
   const quickReplyDraftRef = useRef({ text: quickReplyText, sending: isSendingQuickReply, save: onSaveQuickReplyDraft });
   quickReplyDraftRef.current = { text: quickReplyText, sending: isSendingQuickReply, save: onSaveQuickReplyDraft };
   const hasQuickReplyDraft = quickReplyText.trim().length > 0 && !!onSaveQuickReplyDraft;
@@ -1385,7 +1388,12 @@ export function EmailViewer({
     if (!hasQuickReplyDraft) return;
     return registerComposeFlush(async () => {
       const { text, sending, save } = quickReplyDraftRef.current;
-      if (sending || !text.trim() || !save) return;
+      if (!text.trim() || !save) return;
+      if (sending) {
+        const confirm = useExternalRecipientConfirmStore.getState();
+        if (!confirm.pending) return;
+        confirm.cancelAll();
+      }
       await save(text);
     });
   }, [hasQuickReplyDraft]);