From 82c039117a8832324a8d8b9ebb35505cbdc127d2 Mon Sep 17 00:00:00 2001
From: Bohdan Triapitsyn <artmore@protonmail.com>
Date: Sun, 12 Jul 2026 01:12:58 +0300
Subject: [PATCH] fix(queue): back off failed queued auto-sends

---
 .../hooks/useQueuedMessageAutoSend.test.ts    | 21 ++++++++++++
 .../ui/src/hooks/useQueuedMessageAutoSend.ts  | 34 +++++++++++++++++++
 2 files changed, 55 insertions(+)

diff --git a/packages/ui/src/hooks/useQueuedMessageAutoSend.test.ts b/packages/ui/src/hooks/useQueuedMessageAutoSend.test.ts
index 07344834..fad8d66c 100644
--- a/packages/ui/src/hooks/useQueuedMessageAutoSend.test.ts
+++ b/packages/ui/src/hooks/useQueuedMessageAutoSend.test.ts
@@ -29,6 +29,8 @@ mock.module('@/sync/session-ui-store', () => ({
 
 import {
   buildQueuedAutoSendPayload,
+  getQueuedAutoSendRetryDelayMs,
+  isQueuedAutoSendBackedOff,
   sendQueuedAutoSendPayload,
   shouldDispatchQueuedAutoSend,
 } from './useQueuedMessageAutoSend';
@@ -49,6 +51,25 @@ describe('shouldDispatchQueuedAutoSend', () => {
   });
 });
 
+describe('queued auto-send retry backoff', () => {
+  test('delay grows exponentially and is capped', () => {
+    expect(getQueuedAutoSendRetryDelayMs(1)).toBe(2000);
+    expect(getQueuedAutoSendRetryDelayMs(2)).toBe(4000);
+    expect(getQueuedAutoSendRetryDelayMs(3)).toBe(8000);
+    expect(getQueuedAutoSendRetryDelayMs(10)).toBe(60000);
+    expect(getQueuedAutoSendRetryDelayMs(100)).toBe(60000);
+  });
+
+  test('backs off only the failed message within its window', () => {
+    const failure = { messageId: 'queued-1', failures: 1, nextAttemptAt: 10_000 };
+
+    expect(isQueuedAutoSendBackedOff(failure, 'queued-1', 9_999)).toBe(true);
+    expect(isQueuedAutoSendBackedOff(failure, 'queued-1', 10_000)).toBe(false);
+    expect(isQueuedAutoSendBackedOff(failure, 'queued-2', 9_999)).toBe(false);
+    expect(isQueuedAutoSendBackedOff(undefined, 'queued-1', 0)).toBe(false);
+  });
+});
+
 describe('buildQueuedAutoSendPayload', () => {
   beforeEach(() => {
     visibleAgents = [];
diff --git a/packages/ui/src/hooks/useQueuedMessageAutoSend.ts b/packages/ui/src/hooks/useQueuedMessageAutoSend.ts
index ee0c3646..894bdbda 100644
--- a/packages/ui/src/hooks/useQueuedMessageAutoSend.ts
+++ b/packages/ui/src/hooks/useQueuedMessageAutoSend.ts
@@ -13,6 +13,24 @@ type SessionStatusType = 'idle' | 'busy' | 'retry';
 
 const RECENT_ABORT_WINDOW_MS = 2000;
 
+const AUTO_SEND_RETRY_BASE_DELAY_MS = 2000;
+const AUTO_SEND_RETRY_MAX_DELAY_MS = 60000;
+
+export type QueuedAutoSendFailure = {
+  messageId: string;
+  failures: number;
+  nextAttemptAt: number;
+};
+
+export const getQueuedAutoSendRetryDelayMs = (failures: number): number =>
+  Math.min(AUTO_SEND_RETRY_BASE_DELAY_MS * 2 ** Math.max(failures - 1, 0), AUTO_SEND_RETRY_MAX_DELAY_MS);
+
+export const isQueuedAutoSendBackedOff = (
+  failure: QueuedAutoSendFailure | undefined,
+  messageId: string,
+  now: number,
+): boolean => failure !== undefined && failure.messageId === messageId && now < failure.nextAttemptAt;
+
 const hasRecentAbort = (sessionId: string): boolean => {
   const abortRecord = useSessionUIStore.getState().sessionAbortFlags.get(sessionId);
   if (!abortRecord) {
@@ -124,6 +142,7 @@ export function useQueuedMessageAutoSend(enabledOrOptions?: boolean | { enabled?
   const sessionStatusRecord = useDirectorySync((state) => state.session_status);
 
   const inFlightSessionsRef = React.useRef<Set<string>>(new Set());
+  const sendFailuresRef = React.useRef<Map<string, QueuedAutoSendFailure>>(new Map());
   const previousStatusRef = React.useRef<Map<string, SessionStatusType>>(new Map());
   const autoReviewBlockedSessionsRef = React.useRef<Set<string>>(new Set());
 
@@ -157,6 +176,13 @@ export function useQueuedMessageAutoSend(enabledOrOptions?: boolean | { enabled?
         return;
       }
 
+      const failure = sendFailuresRef.current.get(sessionId);
+      if (failure && failure.messageId !== payload.queuedMessageId) {
+        sendFailuresRef.current.delete(sessionId);
+      } else if (isQueuedAutoSendBackedOff(failure, payload.queuedMessageId, Date.now())) {
+        return;
+      }
+
       // Use send config captured at queue time; fall back to current config
       const captured = payload.sendConfig;
       const resolved = captured?.providerID && captured?.modelID
@@ -176,8 +202,16 @@ export function useQueuedMessageAutoSend(enabledOrOptions?: boolean | { enabled?
           variant: resolved.variant,
         });
         useMessageQueueStore.getState().removeFromQueue(sessionId, payload.queuedMessageId);
+        sendFailuresRef.current.delete(sessionId);
       } catch (error) {
         console.warn('[queue] queued auto-send failed:', error);
+        const priorFailures = failure?.messageId === payload.queuedMessageId ? failure.failures : 0;
+        const failures = priorFailures + 1;
+        sendFailuresRef.current.set(sessionId, {
+          messageId: payload.queuedMessageId,
+          failures,
+          nextAttemptAt: Date.now() + getQueuedAutoSendRetryDelayMs(failures),
+        });
       } finally {
         inFlightSessionsRef.current.delete(sessionId);
       }