diff --git a/packages/coding-agent/CHANGELOG.md b/packages/coding-agent/CHANGELOG.md
index 6c5d526e2..ff2122782 100644
--- a/packages/coding-agent/CHANGELOG.md
+++ b/packages/coding-agent/CHANGELOG.md
@@ -2,6 +2,10 @@
 
 ## [Unreleased]
 
+### Fixed
+
+- Fixed the ask tool timeout so it auto-selects the recommended option even when the UI selector does not settle on its own. ([#4995](https://github.com/can1357/oh-my-pi/issues/4995))
+
 ## [16.3.15] - 2026-07-09
 
 ### Changed
diff --git a/packages/coding-agent/src/tools/ask.ts b/packages/coding-agent/src/tools/ask.ts
index 42de7f930..c58ef975a 100644
--- a/packages/coding-agent/src/tools/ask.ts
+++ b/packages/coding-agent/src/tools/ask.ts
@@ -432,10 +432,16 @@ async function askSingleQuestion(
 		const helpText = navigation
 			? "up/down navigate  enter select  ←/→ question  esc cancel"
 			: "up/down navigate  enter select  esc cancel";
+		const timeoutController = typeof timeout === "number" && timeout > 0 ? new AbortController() : undefined;
+		const dialogSignal =
+			signal && timeoutController
+				? AbortSignal.any([signal, timeoutController.signal])
+				: (timeoutController?.signal ?? signal);
+		let timeoutId: NodeJS.Timeout | undefined;
 		const dialogOptions = {
 			initialIndex,
 			timeout,
-			signal,
+			signal: dialogSignal,
 			outline: true,
 			onTimeout,
 			helpText,
@@ -454,18 +460,33 @@ async function askSingleQuestion(
 				: undefined,
 		};
 		const startMs = Date.now();
-		const choice = signal
-			? await untilAborted(signal, () => ui.select(prompt, optionsToShow, dialogOptions))
-			: await ui.select(prompt, optionsToShow, dialogOptions);
-		if (!timeoutTriggered && choice === undefined && typeof timeout === "number") {
-			// Fallback for UI surfaces that enforce `timeout` without invoking
-			// `onTimeout`: their auto-cancel resolves right at the deadline. A
-			// cancel arriving well past the deadline is a deliberate user Esc on
-			// a surface that kept the dialog open — keep treating it as a cancel.
-			const elapsed = Date.now() - startMs;
-			timeoutTriggered = elapsed >= timeout && elapsed <= timeout + TIMEOUT_DETECTION_TOLERANCE_MS;
+		if (timeoutController && typeof timeout === "number") {
+			timeoutId = setTimeout(() => {
+				timeoutTriggered = true;
+				timeoutController.abort();
+			}, timeout);
+		}
+		try {
+			const choice = dialogSignal
+				? await untilAborted(dialogSignal, () => ui.select(prompt, optionsToShow, dialogOptions))
+				: await ui.select(prompt, optionsToShow, dialogOptions);
+			if (!timeoutTriggered && choice === undefined && typeof timeout === "number") {
+				// Fallback for UI surfaces that enforce `timeout` without invoking
+				// `onTimeout`: their auto-cancel resolves right at the deadline. A
+				// cancel arriving well past the deadline is a deliberate user Esc on
+				// a surface that kept the dialog open — keep treating it as a cancel.
+				const elapsed = Date.now() - startMs;
+				timeoutTriggered = elapsed >= timeout && elapsed <= timeout + TIMEOUT_DETECTION_TOLERANCE_MS;
+			}
+			return { choice, timedOut: timeoutTriggered, navigation: navigationAction };
+		} catch (error) {
+			if (timeoutTriggered && error instanceof Error && error.name === "AbortError") {
+				return { choice: undefined, timedOut: true, navigation: navigationAction };
+			}
+			throw error;
+		} finally {
+			clearTimeout(timeoutId);
 		}
-		return { choice, timedOut: timeoutTriggered, navigation: navigationAction };
 	};
 
 	const promptForCustomInput = async (
diff --git a/packages/coding-agent/test/ask-timeout.test.ts b/packages/coding-agent/test/ask-timeout.test.ts
new file mode 100644
index 000000000..ebbf14f67
--- /dev/null
+++ b/packages/coding-agent/test/ask-timeout.test.ts
@@ -0,0 +1,91 @@
+import { afterEach, beforeAll, describe, expect, it, vi } from "bun:test";
+import type { AgentToolContext, AgentToolResult } from "@oh-my-pi/pi-agent-core";
+import { getThemeByName, setThemeInstance } from "../src/modes/theme/theme";
+import type { ToolSession } from "../src/tools";
+import { AskTool, type AskToolDetails } from "../src/tools/ask";
+
+type AskExecutionResult = AgentToolResult<AskToolDetails>;
+
+async function drainMicrotasks(): Promise<void> {
+	await Promise.resolve();
+	await Promise.resolve();
+}
+
+function createAskTool(): AskTool {
+	return new AskTool({
+		hasUI: true,
+		settings: {
+			get(key: string): unknown {
+				if (key === "ask.timeout") return 0.01;
+				if (key === "ask.notify") return "off";
+				if (key === "speech.enabled") return false;
+				return undefined;
+			},
+		},
+		getPlanModeState: () => ({ enabled: false }),
+	} as unknown as ToolSession);
+}
+
+describe("AskTool timeout", () => {
+	beforeAll(async () => {
+		const loaded = await getThemeByName("dark");
+		if (!loaded) throw new Error("theme unavailable");
+		setThemeInstance(loaded);
+	});
+
+	afterEach(() => {
+		vi.useRealTimers();
+		vi.restoreAllMocks();
+	});
+
+	it("auto-selects the recommended option when the selector does not settle", async () => {
+		vi.useFakeTimers();
+		const select = vi.fn(() => new Promise<string | undefined>(() => {}));
+		const abort = vi.fn();
+		const context = {
+			hasUI: true,
+			ui: {
+				select,
+				editor: vi.fn(),
+			},
+			abort,
+		} as unknown as AgentToolContext;
+		let result: AskExecutionResult | undefined;
+		let rejection: unknown;
+
+		void createAskTool()
+			.execute(
+				"ask-timeout",
+				{
+					questions: [
+						{
+							id: "db",
+							question: "Which database?",
+							options: [{ label: "SQLite" }, { label: "Postgres" }],
+							recommended: 1,
+						},
+					],
+				},
+				undefined,
+				undefined,
+				context,
+			)
+			.then(
+				value => {
+					result = value;
+				},
+				error => {
+					rejection = error;
+				},
+			);
+
+		await drainMicrotasks();
+		vi.advanceTimersByTime(10);
+		await drainMicrotasks();
+
+		expect(rejection).toBeUndefined();
+		expect(result?.details?.selectedOptions).toEqual(["Postgres"]);
+		expect(result?.details?.timedOut).toBe(true);
+		expect(abort).not.toHaveBeenCalled();
+	});
+});