From 75213f6a551278c295a6e95246dc15a6cbf1e101 Mon Sep 17 00:00:00 2001
From: Linus Rath <139418639+rathlinus@users.noreply.github.com>
Date: Sat, 31 Oct 2026 18:32:21 +0100
Subject: [PATCH] fix: send a message queued or retried while the outbox is
 already sending

---
 .../__tests__/outbox-send-queue.test.ts       | 31 +++++++++++++++++++
 src/stores/outbox-store.ts                    | 15 +++++++--
 2 files changed, 44 insertions(+), 2 deletions(-)

diff --git a/src/stores/__tests__/outbox-send-queue.test.ts b/src/stores/__tests__/outbox-send-queue.test.ts
index 11655c32..c7555456 100644
--- a/src/stores/__tests__/outbox-send-queue.test.ts
+++ b/src/stores/__tests__/outbox-send-queue.test.ts
@@ -141,6 +141,37 @@ describe('offline send queue', () => {
     expect(runQueuedSend).toHaveBeenCalledTimes(1);
   });
 
+  it('sends a message queued while another one is on its way', async () => {
+    let release!: () => void;
+    runQueuedSend.mockImplementationOnce(() => new Promise((r) => { release = () => r({ kind: 'sent', result: {} }); }));
+    useNetworkStore.setState({ online: true, connected: true });
+    useOutboxStore.getState().enqueueSend(payload('first'));
+    await flushed();
+    expect(runQueuedSend).toHaveBeenCalledTimes(1);
+    useOutboxStore.getState().enqueueSend(payload('second'));
+    release();
+    await vi.waitFor(() => expect(useOutboxStore.getState().sends).toEqual([]));
+    expect(runQueuedSend.mock.calls.map(([s]) => s.payload.outgoing.subject)).toEqual(['first', 'second']);
+  });
+
+  it('sends a message retried while another one is on its way', async () => {
+    useNetworkStore.setState({ online: true, connected: true });
+    runQueuedSend.mockRejectedValueOnce(new Error('Invalid envelope'));
+    const failed = useOutboxStore.getState().enqueueSend(payload('failed'))!;
+    await vi.waitFor(() => expect(useOutboxStore.getState().sends[0]?.status).toBe('failed'));
+
+    let release!: () => void;
+    runQueuedSend.mockImplementationOnce(() => new Promise((r) => { release = () => r({ kind: 'sent', result: {} }); }));
+    useOutboxStore.getState().enqueueSend(payload('other'));
+    await flushed();
+    expect(runQueuedSend).toHaveBeenCalledTimes(2);
+    const retried = useOutboxStore.getState().retrySend(failed);
+    release();
+    await retried;
+    await vi.waitFor(() => expect(useOutboxStore.getState().sends).toEqual([]));
+    expect(runQueuedSend.mock.calls.map(([s]) => s.payload.outgoing.subject)).toEqual(['failed', 'other', 'failed']);
+  });
+
   it('parks a refused message with its reason and leaves it until the user tries again', async () => {
     useNetworkStore.setState({ online: true, connected: true });
     runQueuedSend.mockRejectedValueOnce(new Error('Invalid envelope'));
diff --git a/src/stores/outbox-store.ts b/src/stores/outbox-store.ts
index ab4c7350..a052bb2c 100644
--- a/src/stores/outbox-store.ts
+++ b/src/stores/outbox-store.ts
@@ -258,6 +258,12 @@ function opFamily(op: OutboxOp): string {
 
 let retryTimer: ReturnType<typeof setTimeout> | null = null;
 let retryAttempt = 0;
+/**
+ * A flush was asked for while one ran (a message queued or retried then):
+ * the running one works from lists it took when it started, so another
+ * follows it.
+ */
+let flushAgain = false;
 
 // Reads of a bucket from storage. A read still running when the account
 // changes or its queue is cleared must not put the old entries back, so
@@ -436,7 +442,11 @@ export const useOutboxStore = create<OutboxState>((set, get) => ({
   pendingForEmail: (emailId) => get().entries.filter((e) => e.op.emailId === emailId),
 
   flush: async () => {
-    if (get().flushing || get().paused || !get().resumed || !get().hydrated) return;
+    if (get().flushing) {
+      flushAgain = true;
+      return;
+    }
+    if (get().paused || !get().resumed || !get().hydrated) return;
     const accountId = get().activeAccountId;
     if (!accountId) return;
     if (get().entries.length === 0 && !hasWaitingSends()) return;
@@ -445,6 +455,7 @@ export const useOutboxStore = create<OutboxState>((set, get) => ({
     if (!useNetworkStore.getState().online) return;
 
     set({ flushing: true });
+    flushAgain = false;
     let brokeTransient = false;
     let dropped = false;
     // An entry that took on a later edit while its op was out runs again.
@@ -509,7 +520,7 @@ export const useOutboxStore = create<OutboxState>((set, get) => ({
       set({ flushing: false });
     }
     if (brokeTransient && (get().entries.length > 0 || hasWaitingSends())) scheduleRetry();
-    else if (changedInFlight) void get().flush();
+    else if (changedInFlight || flushAgain) void get().flush();
     if (dropped) void refreshAfterDrop();
   },