diff --git a/packages/cli/src/ui/AppContainer.test.tsx b/packages/cli/src/ui/AppContainer.test.tsx
index 7e6b01e26d..02a9250614 100644
--- a/packages/cli/src/ui/AppContainer.test.tsx
+++ b/packages/cli/src/ui/AppContainer.test.tsx
@@ -943,11 +943,11 @@ describe('AppContainer State Management', () => {
 
   describe('Cancel Handler (issue #3204)', () => {
     // The cancel handler is wired through useGeminiStream's onCancelSubmit
-    // arg (positional index 14 — see the useGeminiStream call site in
+    // arg (positional index 15 — see the useGeminiStream call site in
     // AppContainer.tsx). We capture it via mockImplementation so a future
     // signature change surfaces as a clear test failure rather than silently
     // grabbing the wrong callback.
-    const ON_CANCEL_SUBMIT_ARG_INDEX = 14;
+    const ON_CANCEL_SUBMIT_ARG_INDEX = 15;
     type CapturedCancelSubmit = (info?: {
       pendingItem: HistoryItemWithoutId | null;
       lastTurnUserItem: { id: number; text: string } | null;
diff --git a/packages/cli/src/ui/AppContainer.tsx b/packages/cli/src/ui/AppContainer.tsx
index a680afdac8..a1cc171940 100644
--- a/packages/cli/src/ui/AppContainer.tsx
+++ b/packages/cli/src/ui/AppContainer.tsx
@@ -1483,6 +1483,7 @@ export const AppContainer = (props: AppContainerProps) => {
     historyManager.history,
     historyManager.addItem,
     config,
+    isConfigInitialized,
     settings,
     onDebugMessage,
     handleSlashCommand,
diff --git a/packages/cli/src/ui/hooks/useGeminiStream.test.tsx b/packages/cli/src/ui/hooks/useGeminiStream.test.tsx
index c4a4c1e71a..b13b3b24a6 100644
--- a/packages/cli/src/ui/hooks/useGeminiStream.test.tsx
+++ b/packages/cli/src/ui/hooks/useGeminiStream.test.tsx
@@ -332,6 +332,7 @@ describe('useGeminiStream', () => {
           props.history,
           props.addItem,
           props.config,
+          true,
           props.loadedSettings,
           props.onDebugMessage,
           props.handleSlashCommand,
@@ -620,6 +621,7 @@ describe('useGeminiStream', () => {
         [],
         mockAddItem,
         mockConfig,
+        true,
         mockLoadedSettings,
         mockOnDebugMessage,
         mockHandleSlashCommand,
@@ -719,6 +721,7 @@ describe('useGeminiStream', () => {
         [],
         mockAddItem,
         mockConfig,
+        true,
         mockLoadedSettings,
         mockOnDebugMessage,
         mockHandleSlashCommand,
@@ -854,6 +857,7 @@ describe('useGeminiStream', () => {
         [],
         mockAddItem,
         mockConfig,
+        true,
         mockLoadedSettings,
         mockOnDebugMessage,
         mockHandleSlashCommand,
@@ -996,6 +1000,7 @@ describe('useGeminiStream', () => {
         [],
         mockAddItem,
         mockConfig,
+        true,
         mockLoadedSettings,
         mockOnDebugMessage,
         mockHandleSlashCommand,
@@ -1115,6 +1120,7 @@ describe('useGeminiStream', () => {
         [],
         mockAddItem,
         mockConfig,
+        true,
         mockLoadedSettings,
         mockOnDebugMessage,
         mockHandleSlashCommand,
@@ -1239,6 +1245,7 @@ describe('useGeminiStream', () => {
         [],
         mockAddItem,
         mockConfig,
+        true,
         mockLoadedSettings,
         mockOnDebugMessage,
         mockHandleSlashCommand,
@@ -1352,6 +1359,7 @@ describe('useGeminiStream', () => {
         [],
         mockAddItem,
         mockConfig,
+        true,
         mockLoadedSettings,
         mockOnDebugMessage,
         mockHandleSlashCommand,
@@ -1458,6 +1466,7 @@ describe('useGeminiStream', () => {
         [],
         mockAddItem,
         mockConfig,
+        true,
         mockLoadedSettings,
         mockOnDebugMessage,
         mockHandleSlashCommand,
@@ -1557,6 +1566,7 @@ describe('useGeminiStream', () => {
         [],
         mockAddItem,
         mockConfig,
+        true,
         mockLoadedSettings,
         mockOnDebugMessage,
         mockHandleSlashCommand,
@@ -1645,6 +1655,7 @@ describe('useGeminiStream', () => {
         [],
         mockAddItem,
         mockConfig,
+        true,
         mockLoadedSettings,
         mockOnDebugMessage,
         mockHandleSlashCommand,
@@ -1757,6 +1768,7 @@ describe('useGeminiStream', () => {
         [],
         mockAddItem,
         mockConfig,
+        true,
         mockLoadedSettings,
         mockOnDebugMessage,
         mockHandleSlashCommand,
@@ -1861,6 +1873,7 @@ describe('useGeminiStream', () => {
         [],
         mockAddItem,
         mockConfig,
+        true,
         mockLoadedSettings,
         mockOnDebugMessage,
         mockHandleSlashCommand,
@@ -2140,6 +2153,7 @@ describe('useGeminiStream', () => {
         [],
         mockAddItem,
         mockConfig,
+        true,
         mockLoadedSettings,
         mockOnDebugMessage,
         mockHandleSlashCommand,
@@ -2278,6 +2292,7 @@ describe('useGeminiStream', () => {
         [],
         mockAddItem,
         mockConfig,
+        true,
         mockLoadedSettings,
         mockOnDebugMessage,
         mockHandleSlashCommand,
@@ -2425,6 +2440,7 @@ describe('useGeminiStream', () => {
         [],
         mockAddItem,
         mockConfig,
+        true,
         mockLoadedSettings,
         mockOnDebugMessage,
         mockHandleSlashCommand,
@@ -2540,6 +2556,7 @@ describe('useGeminiStream', () => {
         [],
         mockAddItem,
         mockConfig,
+        true,
         mockLoadedSettings,
         mockOnDebugMessage,
         mockHandleSlashCommand,
@@ -2662,6 +2679,7 @@ describe('useGeminiStream', () => {
         [],
         mockAddItem,
         mockConfig,
+        true,
         mockLoadedSettings,
         mockOnDebugMessage,
         mockHandleSlashCommand,
@@ -2863,6 +2881,7 @@ describe('useGeminiStream', () => {
         [],
         mockAddItem,
         mockConfig,
+        true,
         mockLoadedSettings,
         mockOnDebugMessage,
         mockHandleSlashCommand,
@@ -2988,6 +3007,7 @@ describe('useGeminiStream', () => {
         [],
         mockAddItem,
         mockConfig,
+        true,
         mockLoadedSettings,
         mockOnDebugMessage,
         mockHandleSlashCommand,
@@ -3126,6 +3146,7 @@ describe('useGeminiStream', () => {
           historyWithToolGroup,
           mockAddItem,
           config,
+          true,
           mockLoadedSettings,
           mockOnDebugMessage,
           mockHandleSlashCommand,
@@ -3307,6 +3328,7 @@ describe('useGeminiStream', () => {
           history,
           mockAddItem,
           config,
+          true,
           mockLoadedSettings,
           mockOnDebugMessage,
           mockHandleSlashCommand,
@@ -3804,6 +3826,7 @@ describe('useGeminiStream', () => {
           [],
           mockAddItem,
           mockConfig,
+          true,
           mockLoadedSettings,
           mockOnDebugMessage,
           mockHandleSlashCommand,
@@ -3853,6 +3876,7 @@ describe('useGeminiStream', () => {
           [],
           mockAddItem,
           mockConfig,
+          true,
           mockLoadedSettings,
           mockOnDebugMessage,
           mockHandleSlashCommand,
@@ -3909,6 +3933,7 @@ describe('useGeminiStream', () => {
           [],
           mockAddItem,
           mockConfig,
+          true,
           mockLoadedSettings,
           mockOnDebugMessage,
           mockHandleSlashCommand,
@@ -3968,6 +3993,7 @@ describe('useGeminiStream', () => {
           [],
           mockAddItem,
           mockConfig,
+          true,
           mockLoadedSettings,
           mockOnDebugMessage,
           mockHandleSlashCommand,
@@ -4049,6 +4075,7 @@ describe('useGeminiStream', () => {
           [],
           mockAddItem,
           mockConfig,
+          true,
           mockLoadedSettings,
           mockOnDebugMessage,
           mockHandleSlashCommand,
@@ -4104,6 +4131,7 @@ describe('useGeminiStream', () => {
           [],
           mockAddItem,
           mockConfig,
+          true,
           mockLoadedSettings,
           mockOnDebugMessage,
           mockHandleSlashCommand,
@@ -4161,6 +4189,7 @@ describe('useGeminiStream', () => {
           [],
           mockAddItem,
           mockConfig,
+          true,
           mockLoadedSettings,
           mockOnDebugMessage,
           mockHandleSlashCommand,
@@ -4234,6 +4263,7 @@ describe('useGeminiStream', () => {
           [],
           mockAddItem,
           mockConfig,
+          true,
           mockLoadedSettings,
           mockOnDebugMessage,
           mockHandleSlashCommand,
@@ -4582,6 +4612,7 @@ describe('useGeminiStream', () => {
           [],
           mockAddItem,
           mockConfig,
+          true,
           mockLoadedSettings,
           mockOnDebugMessage,
           mockHandleSlashCommand,
@@ -4639,6 +4670,7 @@ describe('useGeminiStream', () => {
           [],
           mockAddItem,
           testConfig,
+          true,
           mockLoadedSettings,
           mockOnDebugMessage,
           mockHandleSlashCommand,
@@ -5132,6 +5164,7 @@ describe('useGeminiStream', () => {
           [],
           mockAddItem,
           mockConfig,
+          true,
           mockLoadedSettings,
           mockOnDebugMessage,
           mockHandleSlashCommand,
@@ -5187,6 +5220,7 @@ describe('useGeminiStream', () => {
           [],
           mockAddItem,
           mockConfig,
+          true,
           mockLoadedSettings,
           mockOnDebugMessage,
           mockHandleSlashCommand,
@@ -5243,6 +5277,7 @@ describe('useGeminiStream', () => {
           [],
           mockAddItem,
           mockConfig,
+          true,
           mockLoadedSettings,
           mockOnDebugMessage,
           mockHandleSlashCommand,
@@ -5355,6 +5390,7 @@ describe('useGeminiStream', () => {
             [],
             mockAddItem,
             mockConfig,
+            true,
             mockLoadedSettings,
             mockOnDebugMessage,
             mockHandleSlashCommand,
@@ -5409,6 +5445,7 @@ describe('useGeminiStream', () => {
         [],
         mockAddItem,
         mockConfig,
+        true,
         mockLoadedSettings,
         mockOnDebugMessage,
         mockHandleSlashCommand,
@@ -5483,6 +5520,7 @@ describe('useGeminiStream', () => {
           [],
           mockAddItem,
           mockConfig,
+          true,
           mockLoadedSettings,
           mockOnDebugMessage,
           mockHandleSlashCommand,
@@ -5580,6 +5618,7 @@ describe('useGeminiStream', () => {
           [],
           mockAddItem,
           mockConfig,
+          true,
           mockLoadedSettings,
           mockOnDebugMessage,
           mockHandleSlashCommand,
@@ -5986,6 +6025,7 @@ describe('useGeminiStream', () => {
             [],
             mockAddItem,
             mockConfig,
+            true,
             mockLoadedSettings,
             mockOnDebugMessage,
             mockHandleSlashCommand,
@@ -6102,6 +6142,7 @@ describe('useGeminiStream', () => {
             [],
             mockAddItem,
             mockConfig,
+            true,
             mockLoadedSettings,
             mockOnDebugMessage,
             mockHandleSlashCommand,
@@ -6175,6 +6216,7 @@ describe('useGeminiStream', () => {
           [],
           mockAddItem,
           mockConfig,
+          true,
           mockLoadedSettings,
           mockOnDebugMessage,
           mockHandleSlashCommand,
@@ -6245,6 +6287,7 @@ describe('useGeminiStream', () => {
           [],
           mockAddItem,
           mockConfig,
+          true,
           mockLoadedSettings,
           mockOnDebugMessage,
           mockHandleSlashCommand,
@@ -6374,6 +6417,7 @@ describe('useGeminiStream', () => {
           [],
           mockAddItem,
           mockConfig,
+          true,
           mockLoadedSettings,
           mockOnDebugMessage,
           mockHandleSlashCommand,
@@ -6429,6 +6473,7 @@ describe('useGeminiStream', () => {
           [],
           mockAddItem,
           mockConfig,
+          true,
           mockLoadedSettings,
           mockOnDebugMessage,
           mockHandleSlashCommand,
@@ -7498,6 +7543,150 @@ describe('useGeminiStream', () => {
       });
     });
   });
+
+  describe('cron scheduler initialization', () => {
+    // Renders useGeminiStream wired to a provided cron scheduler mock, with a
+    // controllable isConfigInitialized gate. `config` identity is stable across
+    // rerenders so the cron effect only re-runs when `initialized` flips.
+    const renderCronHook = (scheduler: unknown, initialized: boolean) => {
+      const cronConfig = {
+        ...mockConfig,
+        isCronEnabled: vi.fn(() => true),
+        getCronScheduler: vi.fn(() => scheduler),
+      } as unknown as Config;
+      return renderHook(
+        (props: { initialized: boolean }) =>
+          useGeminiStream(
+            new MockedGeminiClientClass(cronConfig),
+            [],
+            mockAddItem,
+            cronConfig,
+            props.initialized,
+            mockLoadedSettings,
+            mockOnDebugMessage,
+            mockHandleSlashCommand as unknown as (
+              cmd: PartListUnion,
+            ) => Promise<SlashCommandProcessorResult | false>,
+            false,
+            () => 'vscode' as EditorType,
+            () => {},
+            () => Promise.resolve(),
+            false,
+            () => {},
+            () => {},
+            () => {},
+            () => {},
+            80,
+            24,
+          ),
+        { initialProps: { initialized } },
+      );
+    };
+
+    it('defers enableDurable and start until isConfigInitialized is true', async () => {
+      const callOrder: string[] = [];
+      const scheduler = {
+        // A real async gap before recording: a synchronous push would make the
+        // order assertion pass even if production dropped the `await`.
+        enableDurable: vi.fn().mockImplementation(async () => {
+          await new Promise((r) => setTimeout(r, 10));
+          callOrder.push('enableDurable');
+        }),
+        start: vi.fn().mockImplementation(() => {
+          callOrder.push('start');
+        }),
+        stop: vi.fn(),
+        getExitSummary: vi.fn(() => null),
+        hasPendingWork: false,
+      };
+
+      const { rerender } = renderCronHook(scheduler, false);
+
+      // Before initialization: the scheduler must not be touched.
+      expect(scheduler.enableDurable).not.toHaveBeenCalled();
+      expect(scheduler.start).not.toHaveBeenCalled();
+
+      rerender({ initialized: true });
+
+      await waitFor(() => {
+        expect(scheduler.start).toHaveBeenCalled();
+      });
+      // enableDurable is awaited before start despite the 10ms gap.
+      expect(callOrder).toEqual(['enableDurable', 'start']);
+    });
+
+    it('does not start scheduler when isConfigInitialized remains false', async () => {
+      const scheduler = {
+        enableDurable: vi.fn().mockResolvedValue(undefined),
+        start: vi.fn(),
+        stop: vi.fn(),
+        getExitSummary: vi.fn(() => null),
+        hasPendingWork: false,
+      };
+
+      renderCronHook(scheduler, false);
+
+      // Give effects time to run.
+      await new Promise((resolve) => setTimeout(resolve, 50));
+
+      expect(scheduler.enableDurable).not.toHaveBeenCalled();
+      expect(scheduler.start).not.toHaveBeenCalled();
+    });
+
+    it('does not start scheduler if unmounted during the enableDurable gap', async () => {
+      // enableDurable stays pending until we resolve it by hand, so we can
+      // unmount inside the async gap — the exact race the `stopped` flag guards.
+      let resolveEnable: () => void = () => {};
+      const scheduler = {
+        enableDurable: vi.fn().mockImplementation(
+          () =>
+            new Promise<void>((resolve) => {
+              resolveEnable = resolve;
+            }),
+        ),
+        start: vi.fn(),
+        stop: vi.fn(),
+        getExitSummary: vi.fn(() => null),
+        hasPendingWork: false,
+      };
+
+      const { unmount } = renderCronHook(scheduler, true);
+
+      await waitFor(() => {
+        expect(scheduler.enableDurable).toHaveBeenCalled();
+      });
+      expect(scheduler.start).not.toHaveBeenCalled();
+
+      // Unmount while enableDurable is still in flight, then let it resolve.
+      unmount();
+      resolveEnable();
+      await new Promise((resolve) => setTimeout(resolve, 10));
+
+      // The stopped guard must suppress the late start(); cleanup ran stop().
+      expect(scheduler.start).not.toHaveBeenCalled();
+      expect(scheduler.stop).toHaveBeenCalled();
+    });
+
+    it('still starts the scheduler when enableDurable rejects', async () => {
+      const scheduler = {
+        enableDurable: vi.fn().mockRejectedValue(new Error('lock contention')),
+        start: vi.fn(),
+        stop: vi.fn(),
+        getExitSummary: vi.fn(() => null),
+        hasPendingWork: false,
+      };
+
+      renderCronHook(scheduler, true);
+
+      // A failed enableDurable must NOT skip start(): session-only cron tasks
+      // (created via cron_create during this session) still need the scheduler
+      // running — only durable/persistent tasks are lost. Regression guard for
+      // the catch falling through instead of returning (#5022 review).
+      await waitFor(() => {
+        expect(scheduler.start).toHaveBeenCalled();
+      });
+    });
+  });
 });
 
 describe('classifyApiError', () => {
diff --git a/packages/cli/src/ui/hooks/useGeminiStream.ts b/packages/cli/src/ui/hooks/useGeminiStream.ts
index 1233eabe37..a5bf15f657 100644
--- a/packages/cli/src/ui/hooks/useGeminiStream.ts
+++ b/packages/cli/src/ui/hooks/useGeminiStream.ts
@@ -349,6 +349,7 @@ export const useGeminiStream = (
   history: HistoryItem[],
   addItem: UseHistoryManagerReturn['addItem'],
   config: Config,
+  isConfigInitialized: boolean,
   settings: LoadedSettings,
   onDebugMessage: (message: string) => void,
   handleSlashCommand: (
@@ -2924,44 +2925,68 @@ export const useGeminiStream = (
   const cronSessionIdRef = useRef(sessionStates.sessionId);
   cronSessionIdRef.current = sessionStates.sessionId;
 
-  // Start the cron scheduler on mount, stop on unmount.
+  // Start the cron scheduler once config is initialized, stop on unmount.
   // Cron fires enqueue onto the shared notification queue.
+  // Gated on isConfigInitialized: without this gate, enableDurable() runs
+  // before config.initialize() completes, and overdue-task fires delivered
+  // through the notification drain reach a chat client whose startChat() has
+  // not yet run — producing "Chat not initialized" on every fresh launch
+  // that has pending durable work (#5022). This matches the ordering the
+  // ACP (Session.ts) and headless (nonInteractiveCli.ts) paths already use.
   useEffect(() => {
+    if (!isConfigInitialized) return;
     if (!config.isCronEnabled()) return;
     const scheduler = config.getCronScheduler();
 
-    // Enable durable (file-backed) cron support (loads tasks from the
-    // user's per-project runtime dir, acquires the lock). The tasks file
-    // lives under ~/.qwen, not the working tree, so it's user-owned rather
-    // than project-controlled — no folder-trust gate needed; the user's
-    // own loops run regardless of how the folder is trusted.
-    // Missed one-shots arrive as late fires through the start() callback.
-    void scheduler.enableDurable(cronSessionIdRef.current).catch((err) => {
-      debugLogger.warn(
-        `Durable cron init failed — persistent tasks will not fire in this session: ${err}`,
+    let stopped = false;
+    // Await enableDurable before start so overdue fires buffer into
+    // pendingFires (onFire is still null) and flush through start()'s
+    // buffer-drain — matching the ACP and headless startup order.
+    void (async () => {
+      try {
+        // Enable durable (file-backed) cron support (loads tasks from the
+        // user's per-project runtime dir, acquires the lock). The tasks file
+        // lives under ~/.qwen, not the working tree, so it's user-owned
+        // rather than project-controlled — no folder-trust gate needed; the
+        // user's own loops run regardless of how the folder is trusted.
+        // Missed one-shots arrive as late fires through the start() callback.
+        await scheduler.enableDurable(cronSessionIdRef.current);
+      } catch (err) {
+        // Fall through (no `return`): a failed enableDurable must NOT skip
+        // start(), or session-only cron tasks (created via cron_create during
+        // this session) would silently never fire. Only durable/persistent
+        // tasks are lost when enableDurable fails. Pre-#5022 the unconditional
+        // start() preserved this; keep that behavior.
+        debugLogger.warn(
+          `Durable cron init failed — persistent tasks will not fire in this session: ${err}`,
+        );
+      }
+      // Unmount may have happened during the await above; the cleanup below
+      // already ran scheduler.stop(), so do not (re)install onFire.
+      if (stopped) return;
+      scheduler.start(
+        (job: { prompt: string; cronExpr?: string; missed?: boolean }) => {
+          const label = job.prompt.slice(0, 40);
+          const source = job.cronExpr === '@wakeup' ? 'Loop' : 'Cron';
+          notificationQueueRef.current.push({
+            displayText: `${job.missed ? 'Missed' : source}: ${label}`,
+            modelText: job.prompt,
+            sendMessageType: SendMessageType.Cron,
+          });
+          setNotificationTrigger((n) => n + 1);
+        },
       );
-    });
+    })();
 
-    scheduler.start(
-      (job: { prompt: string; cronExpr?: string; missed?: boolean }) => {
-        const label = job.prompt.slice(0, 40);
-        const source = job.cronExpr === '@wakeup' ? 'Loop' : 'Cron';
-        notificationQueueRef.current.push({
-          displayText: `${job.missed ? 'Missed' : source}: ${label}`,
-          modelText: job.prompt,
-          sendMessageType: SendMessageType.Cron,
-        });
-        setNotificationTrigger((n) => n + 1);
-      },
-    );
     return () => {
+      stopped = true;
       const summary = scheduler.getExitSummary();
       scheduler.stop();
       if (summary) {
         process.stderr.write(summary + '\n');
       }
     };
-  }, [config]);
+  }, [config, isConfigInitialized]);
 
   // Register background agent notification callback onto the shared queue.
   useEffect(() => {