From 1c33f8daef03103accd2b9310a96587cbd9aff25 Mon Sep 17 00:00:00 2001
From: Linus Rath <139418639+rathlinus@users.noreply.github.com>
Date: Sat, 31 Oct 2026 18:24:12 +0100
Subject: [PATCH] fix: tell the user when a queued message gives up after
 unconfirmed attempts

---
 .../__tests__/outbox-send-queue.test.ts       | 33 +++++++++++++++++++
 src/stores/outbox-store.ts                    |  9 +++--
 2 files changed, 39 insertions(+), 3 deletions(-)

diff --git a/src/stores/__tests__/outbox-send-queue.test.ts b/src/stores/__tests__/outbox-send-queue.test.ts
index 3985256d..46bc6715 100644
--- a/src/stores/__tests__/outbox-send-queue.test.ts
+++ b/src/stores/__tests__/outbox-send-queue.test.ts
@@ -154,6 +154,39 @@ describe('offline send queue', () => {
     expect(useOutboxStore.getState().sends).toEqual([]);
   });
 
+  it('says so when a message fails after too many unconfirmed attempts, as for a refused one', async () => {
+    useNetworkStore.setState({ online: true, connected: true });
+    runQueuedSend.mockRejectedValueOnce(new Error('Invalid envelope'));
+    useOutboxStore.getState().enqueueSend(payload('refused'));
+    await flushed();
+    await flushed();
+    expect(toast.error).toHaveBeenCalledTimes(1);
+    expect(toast.error.mock.calls[0][1]).toEqual({ message: 'refused: Invalid envelope' });
+
+    toast.error.mockClear();
+    const id = useOutboxStore.getState().enqueueSend(payload('unconfirmed'))!;
+    useOutboxStore.setState({ sends: useOutboxStore.getState().sends.map((s) => (s.id === id ? { ...s, attempts: 2 } : s)) });
+    runQueuedSend.mockRejectedValueOnce(named('SendUnconfirmedError', 'Send confirmation was not received'));
+    useOutboxStore.setState({ flushing: false });
+    await useOutboxStore.getState().flush();
+    await flushed();
+    expect(useOutboxStore.getState().sends.find((s) => s.id === id)).toMatchObject({ status: 'failed', attempts: 3 });
+    expect(toast.error).toHaveBeenCalledTimes(1);
+    expect(toast.error.mock.calls[0]).toEqual([
+      'A message in the Outbox could not be sent', { message: 'unconfirmed: Send confirmation was not received' },
+    ]);
+  });
+
+  it('does not report an unconfirmed attempt that will be tried again', async () => {
+    useNetworkStore.setState({ online: true, connected: true });
+    runQueuedSend.mockRejectedValueOnce(named('SendUnconfirmedError', 'Send confirmation was not received'));
+    useOutboxStore.getState().enqueueSend(payload());
+    await flushed();
+    await flushed();
+    expect(useOutboxStore.getState().sends[0]).toMatchObject({ status: 'queued', attempts: 1 });
+    expect(toast.error).not.toHaveBeenCalled();
+  });
+
   it('stops after an expired session without failing the message', async () => {
     useNetworkStore.setState({ online: true, connected: true });
     runQueuedSend.mockRejectedValueOnce(named('AuthenticationError', 'Session expired'));
diff --git a/src/stores/outbox-store.ts b/src/stores/outbox-store.ts
index 3dd97d8f..d0ea2aef 100644
--- a/src/stores/outbox-store.ts
+++ b/src/stores/outbox-store.ts
@@ -690,14 +690,17 @@ async function flushSends(accountId: string): Promise<'done' | 'transient'> {
     } catch (err) {
       const kind = classifySendFailure(err, isTransientNetworkError);
       const message = err instanceof Error ? err.message : String(err);
-      updateSend(accountId, afterFailure(started, kind, message));
+      const next = afterFailure(started, kind, message);
+      updateSend(accountId, next);
+      // Refused, or unconfirmed too often: it waits for the user now, and
+      // nothing retries it, so say so whatever the reason.
+      if (next.status === 'failed') void notifyQueuedSendFailed(started, message);
       if (kind === 'auth') {
         useOutboxStore.setState({ paused: true });
         break;
       }
       if (kind === 'offline' || kind === 'unconfirmed') return 'transient';
-      // Refused: this one waits for the user; the others go on.
-      void notifyQueuedSendFailed(started, message);
+      // Refused: the others go on.
     }
   }
   return 'done';