diff --git a/src/main/index.ts b/src/main/index.ts
index f64ee99..2f0e13a 100644
--- a/src/main/index.ts
+++ b/src/main/index.ts
@@ -22,7 +22,7 @@ import { createInboxWindow, getInboxWindow } from './windows/inboxWindow.js';
 import {
   createQuickCaptureWindow, showQuickCapture, getQuickCaptureWindow
 } from './windows/quickCaptureWindow.js';
-import { createTray, refreshTray, refreshTrayOllama } from './tray.js';
+import { createTray, refreshTray, refreshTrayOllama, refreshTrayFailedCount } from './tray.js';
 import { MediaGc } from './services/MediaGc.js';
 import { BackupService } from './services/BackupService.js';
 import { ExportService } from './services/ExportService.js';
@@ -92,6 +92,7 @@ app.whenReady().then(async () => {
       pushNoteUpdated(getInboxWindow, note);
       // F4-C: AI 처리 완료 = 새 캡처가 inbox 에 합류한 시점, tray 도 즉시 갱신.
       refreshTray(repo.countToday());
+      refreshTrayFailedCount(repo.countFailed());
     },
     logger,
     telemetry
@@ -343,13 +344,15 @@ app.whenReady().then(async () => {
         }).show();
       }
     },
-    /* runOllamaRecheck */ () => { void health.runOnce({ manual: true }); }
+    /* runOllamaRecheck */ () => { void health.runOnce({ manual: true }); },
+    /* runRetryAllFailed */ () => { void capture.retryAllFailed(); }
   );
 
   // F4-C 환경 앵커 — tray tooltip + 메뉴 첫 항목을 오늘 KST 캡처 수로 갱신.
   // 초기 1회 + 60s interval. AiWorker.onUpdate 도 별도 갱신 트리거.
   // cleanup 은 위 통합 before-quit 핸들러에서 처리.
   refreshTray(repo.countToday());
+  refreshTrayFailedCount(repo.countFailed());
   trayInterval = setInterval(() => {
     refreshTray(repo.countToday());
   }, 60_000);
diff --git a/src/main/tray.ts b/src/main/tray.ts
index d905436..9d7e8bc 100644
--- a/src/main/tray.ts
+++ b/src/main/tray.ts
@@ -13,6 +13,8 @@ let _runExportTelemetry: () => void = () => {};
 let _runOllamaRecheck: () => void = () => {};
 let _ollamaOk = true;
 let _todayCount = 0;
+let _runRetryAllFailed: () => void = () => {};
+let _failedCount = 0;
 
 function buildMenu() {
   const items: MenuItemConstructorOptions[] = [];
@@ -34,6 +36,11 @@ function buildMenu() {
     enabled: !_ollamaOk,
     click: _runOllamaRecheck
   });
+  items.push({
+    label: `지금 AI 처리 (실패 ${_failedCount}건)`,
+    enabled: _failedCount > 0,
+    click: _runRetryAllFailed
+  });
   if (app.isPackaged) {
     const { openAtLogin } = app.getLoginItemSettings();
     items.push({
@@ -63,7 +70,8 @@ export function createTray(
   runImport: () => void,
   runSync: () => void,
   runExportTelemetry: () => void,
-  runOllamaRecheck: () => void
+  runOllamaRecheck: () => void,
+  runRetryAllFailed: () => void
 ): TrayType {
   _showInbox = showInbox;
   _showCapture = showCapture;
@@ -73,6 +81,7 @@ export function createTray(
   _runSync = runSync;
   _runExportTelemetry = runExportTelemetry;
   _runOllamaRecheck = runOllamaRecheck;
+  _runRetryAllFailed = runRetryAllFailed;
   const icon = nativeImage.createEmpty();
   tray = new Tray(icon);
   tray.setToolTip(`Inkling — 오늘 ${_todayCount}`);
@@ -101,3 +110,12 @@ export function refreshTrayOllama(ok: boolean): void {
   if (tray === null) return;
   tray.setContextMenu(buildMenu());
 }
+
+/**
+ * v0.2.3 #2 — AiWorker.onUpdate 시 실패 카운트 변하면 메뉴 라벨 + enabled 갱신.
+ */
+export function refreshTrayFailedCount(count: number): void {
+  _failedCount = count;
+  if (tray === null) return;
+  tray.setContextMenu(buildMenu());
+}