diff --git a/packages/junior/src/chat/tools/web/network.ts b/packages/junior/src/chat/tools/web/network.ts
index f9801369..f6694bdd 100644
--- a/packages/junior/src/chat/tools/web/network.ts
+++ b/packages/junior/src/chat/tools/web/network.ts
@@ -265,13 +265,18 @@ export async function withTimeout<T>(
   task: Promise<T>,
   timeoutMs: number,
   label: string,
+  options?: { onTimeout?: () => void },
 ): Promise<T> {
   let timer: ReturnType<typeof setTimeout> | undefined;
   const timeoutPromise = new Promise<never>((_, reject) => {
-    timer = setTimeout(
-      () => reject(new Error(`${label} timed out`)),
-      timeoutMs,
-    );
+    timer = setTimeout(() => {
+      reject(new Error(`${label} timed out`));
+      try {
+        options?.onTimeout?.();
+      } catch {
+        // Timeout semantics must not depend on cleanup success.
+      }
+    }, timeoutMs);
   });
 
   try {
diff --git a/packages/junior/src/chat/tools/web/search.ts b/packages/junior/src/chat/tools/web/search.ts
index 689b9524..b0a2a61f 100644
--- a/packages/junior/src/chat/tools/web/search.ts
+++ b/packages/junior/src/chat/tools/web/search.ts
@@ -97,6 +97,7 @@ export function createWebSearchTool() {
       // search tool on a search-tuned model and only allow an explicit
       // override.
       const model = process.env.AI_WEB_SEARCH_MODEL ?? DEFAULT_SEARCH_MODEL;
+      const controller = new AbortController();
 
       try {
         // AI SDK Gateway reads AI_GATEWAY_API_KEY or ambient Vercel OIDC
@@ -113,9 +114,11 @@ export function createWebSearchTool() {
               }),
             },
             toolChoice: { type: "tool", toolName: SEARCH_TOOL_NAME },
+            abortSignal: controller.signal,
           }),
           SEARCH_TIMEOUT_MS,
           "webSearch",
+          { onTimeout: () => controller.abort() },
         );
 
         const results = parseSearchResults(response.toolResults, maxResults);
diff --git a/packages/junior/tests/unit/web/web-search.test.ts b/packages/junior/tests/unit/web/web-search.test.ts
index 51537469..da55b3fb 100644
--- a/packages/junior/tests/unit/web/web-search.test.ts
+++ b/packages/junior/tests/unit/web/web-search.test.ts
@@ -74,6 +74,7 @@ describe("createWebSearchTool", () => {
         model: { model: "xai/grok-4-fast-reasoning" },
         prompt: "vercel ai gateway",
         toolChoice: { type: "tool", toolName: "parallelSearch" },
+        abortSignal: expect.any(AbortSignal),
       }),
     );
     expect(result).toEqual({
@@ -160,6 +161,93 @@ describe("createWebSearchTool", () => {
     vi.useRealTimers();
   });
 
+  it("aborts the generateText call on timeout", async () => {
+    vi.useFakeTimers();
+    let capturedSignal: AbortSignal | undefined;
+    vi.mocked(generateText).mockImplementation(((opts: {
+      abortSignal?: AbortSignal;
+    }) => {
+      capturedSignal = opts.abortSignal;
+      return new Promise(() => {
+        // Intentionally unresolved to trigger tool timeout.
+      });
+    }) as never);
+
+    const tool = createWebSearchTool();
+    if (typeof tool.execute !== "function") {
+      throw new Error("webSearch execute function missing");
+    }
+
+    const pending = tool.execute({ query: "slow query" }, {} as never);
+    expect(capturedSignal?.aborted).toBe(false);
+    await vi.advanceTimersByTimeAsync(60_000);
+    await pending;
+    expect(capturedSignal?.aborted).toBe(true);
+    vi.useRealTimers();
+  });
+
+  it("does not abort signal on successful search", async () => {
+    let capturedSignal: AbortSignal | undefined;
+    vi.mocked(generateText).mockImplementation(((opts: {
+      abortSignal?: AbortSignal;
+    }) => {
+      capturedSignal = opts.abortSignal;
+      return Promise.resolve({ toolResults: [] });
+    }) as never);
+
+    const tool = createWebSearchTool();
+    if (typeof tool.execute !== "function") {
+      throw new Error("webSearch execute function missing");
+    }
+
+    await tool.execute({ query: "fast query" }, {} as never);
+    expect(capturedSignal?.aborted).toBe(false);
+  });
+
+  it("still reports timeout even if abort signal cleanup throws", async () => {
+    vi.useFakeTimers();
+    const brokenController = new AbortController();
+    const originalAbort = brokenController.abort.bind(brokenController);
+    brokenController.abort = () => {
+      originalAbort();
+      throw new Error("abort listener blew up");
+    };
+
+    // Patch AbortController to return our broken one
+    const originalAC = globalThis.AbortController;
+    globalThis.AbortController = class extends originalAC {
+      constructor() {
+        super();
+        return brokenController as unknown as AbortController;
+      }
+    } as typeof AbortController;
+
+    vi.mocked(generateText).mockImplementation(
+      () =>
+        new Promise(() => {
+          // Intentionally unresolved to trigger tool timeout.
+        }) as never,
+    );
+
+    const tool = createWebSearchTool();
+    if (typeof tool.execute !== "function") {
+      throw new Error("webSearch execute function missing");
+    }
+
+    const pending = tool.execute({ query: "boom query" }, {} as never);
+    await vi.advanceTimersByTimeAsync(60_000);
+    const result = await pending;
+
+    globalThis.AbortController = originalAC;
+
+    expect(result).toMatchObject({
+      ok: false,
+      timeout: true,
+      error: "web search failed: webSearch timed out",
+    });
+    vi.useRealTimers();
+  });
+
   it("marks authentication failures as non-retryable", async () => {
     vi.mocked(generateText).mockRejectedValueOnce(
       new Error(