diff --git a/src/config/sessions.test.ts b/src/config/sessions.test.ts
index 221654659d9..a9ecbf37143 100644
--- a/src/config/sessions.test.ts
+++ b/src/config/sessions.test.ts
@@ -591,4 +591,52 @@ describe("sessions", () => {
     expect(store[mainSessionKey]?.thinkingLevel).toBe("high");
     await expect(fs.stat(`${storePath}.lock`)).rejects.toThrow();
   });
+
+  it("updateSessionStoreEntry re-reads disk inside lock instead of using stale cache", async () => {
+    const mainSessionKey = "agent:main:main";
+    const dir = await createCaseDir("updateSessionStoreEntry-cache-bypass");
+    const storePath = path.join(dir, "sessions.json");
+    await fs.writeFile(
+      storePath,
+      JSON.stringify(
+        {
+          [mainSessionKey]: {
+            sessionId: "sess-1",
+            updatedAt: 123,
+            thinkingLevel: "low",
+          },
+        },
+        null,
+        2,
+      ),
+      "utf-8",
+    );
+
+    // Prime the in-process cache with the original entry.
+    expect(loadSessionStore(storePath)[mainSessionKey]?.thinkingLevel).toBe("low");
+    const originalStat = await fs.stat(storePath);
+
+    // Simulate an external writer that updates the store but preserves mtime.
+    const externalStore = JSON.parse(await fs.readFile(storePath, "utf-8")) as Record<
+      string,
+      Record<string, unknown>
+    >;
+    externalStore[mainSessionKey] = {
+      ...externalStore[mainSessionKey],
+      providerOverride: "anthropic",
+      updatedAt: 124,
+    };
+    await fs.writeFile(storePath, JSON.stringify(externalStore, null, 2), "utf-8");
+    await fs.utimes(storePath, originalStat.atime, originalStat.mtime);
+
+    await updateSessionStoreEntry({
+      storePath,
+      sessionKey: mainSessionKey,
+      update: async () => ({ thinkingLevel: "high" }),
+    });
+
+    const store = loadSessionStore(storePath);
+    expect(store[mainSessionKey]?.providerOverride).toBe("anthropic");
+    expect(store[mainSessionKey]?.thinkingLevel).toBe("high");
+  });
 });
diff --git a/src/config/sessions/store.ts b/src/config/sessions/store.ts
index 9ad45976b1f..d224f368299 100644
--- a/src/config/sessions/store.ts
+++ b/src/config/sessions/store.ts
@@ -806,7 +806,7 @@ export async function updateSessionStoreEntry(params: {
 }): Promise<SessionEntry | null> {
   const { storePath, sessionKey, update } = params;
   return await withSessionStoreLock(storePath, async () => {
-    const store = loadSessionStore(storePath);
+    const store = loadSessionStore(storePath, { skipCache: true });
     const existing = store[sessionKey];
     if (!existing) {
       return null;
diff --git a/src/cron/isolated-agent/run.ts b/src/cron/isolated-agent/run.ts
index 5a66e121281..4de81a3db62 100644
--- a/src/cron/isolated-agent/run.ts
+++ b/src/cron/isolated-agent/run.ts
@@ -154,6 +154,7 @@ export async function runCronIsolatedAgentTurn(params: {
   deps: CliDeps;
   job: CronJob;
   message: string;
+  abortSignal?: AbortSignal;
   sessionKey: string;
   agentId?: string;
   lane?: string;
@@ -454,6 +455,9 @@ export async function runCronIsolatedAgentTurn(params: {
       agentDir,
       fallbacksOverride: resolveAgentModelFallbacksOverride(params.cfg, agentId),
       run: (providerOverride, modelOverride) => {
+        if (params.abortSignal?.aborted) {
+          throw new Error("cron: isolated run aborted");
+        }
         if (isCliProvider(providerOverride, cfgWithAgentDefaults)) {
           const cliSessionId = getCliSessionId(cronSession.sessionEntry, providerOverride);
           return runCliAgent({
@@ -492,6 +496,7 @@ export async function runCronIsolatedAgentTurn(params: {
           runId: cronSession.sessionEntry.sessionId,
           requireExplicitMessageTarget: true,
           disableMessageTool: deliveryRequested,
+          abortSignal: params.abortSignal,
         });
       },
     });
diff --git a/src/cron/service.issue-regressions.test.ts b/src/cron/service.issue-regressions.test.ts
index ac122840750..4e8c9d6f1e7 100644
--- a/src/cron/service.issue-regressions.test.ts
+++ b/src/cron/service.issue-regressions.test.ts
@@ -683,6 +683,55 @@ describe("Cron issue regressions", () => {
     expect(job?.state.lastStatus).toBe("ok");
   });
 
+  it("aborts isolated runs when cron timeout fires", async () => {
+    vi.useRealTimers();
+    const store = await makeStorePath();
+    const scheduledAt = Date.parse("2026-02-15T13:00:00.000Z");
+    const cronJob = createIsolatedRegressionJob({
+      id: "abort-on-timeout",
+      name: "abort timeout",
+      scheduledAt,
+      schedule: { kind: "at", at: new Date(scheduledAt).toISOString() },
+      payload: { kind: "agentTurn", message: "work", timeoutSeconds: 0.01 },
+      state: { nextRunAtMs: scheduledAt },
+    });
+    await writeCronJobs(store.storePath, [cronJob]);
+
+    let now = scheduledAt;
+    let observedAbortSignal: AbortSignal | undefined;
+    const state = createCronServiceState({
+      cronEnabled: true,
+      storePath: store.storePath,
+      log: noopLogger,
+      nowMs: () => now,
+      enqueueSystemEvent: vi.fn(),
+      requestHeartbeatNow: vi.fn(),
+      runIsolatedAgentJob: vi.fn(async ({ abortSignal }) => {
+        observedAbortSignal = abortSignal;
+        await new Promise<void>((resolve) => {
+          if (!abortSignal) {
+            return;
+          }
+          if (abortSignal.aborted) {
+            resolve();
+            return;
+          }
+          abortSignal.addEventListener("abort", () => resolve(), { once: true });
+        });
+        now += 5;
+        return { status: "ok" as const, summary: "late" };
+      }),
+    });
+
+    await onTimer(state);
+
+    expect(observedAbortSignal).toBeDefined();
+    expect(observedAbortSignal?.aborted).toBe(true);
+    const job = state.store?.jobs.find((entry) => entry.id === "abort-on-timeout");
+    expect(job?.state.lastStatus).toBe("error");
+    expect(job?.state.lastError).toContain("timed out");
+  });
+
   it("retries cron schedule computation from the next second when the first attempt returns undefined (#17821)", () => {
     const scheduledAt = Date.parse("2026-02-15T13:00:00.000Z");
     const cronJob = createIsolatedRegressionJob({
diff --git a/src/cron/service/state.ts b/src/cron/service/state.ts
index c331fa1290b..b366da7abc3 100644
--- a/src/cron/service/state.ts
+++ b/src/cron/service/state.ts
@@ -62,7 +62,11 @@ export type CronServiceDeps = {
   wakeNowHeartbeatBusyMaxWaitMs?: number;
   /** WakeMode=now: delay between runHeartbeatOnce retries while busy. */
   wakeNowHeartbeatBusyRetryDelayMs?: number;
-  runIsolatedAgentJob: (params: { job: CronJob; message: string }) => Promise<
+  runIsolatedAgentJob: (params: {
+    job: CronJob;
+    message: string;
+    abortSignal?: AbortSignal;
+  }) => Promise<
     {
       summary?: string;
       /** Last non-empty agent text output (not truncated). */
diff --git a/src/cron/service/timer.ts b/src/cron/service/timer.ts
index 1b6b108dab1..206c82d439f 100644
--- a/src/cron/service/timer.ts
+++ b/src/cron/service/timer.ts
@@ -267,18 +267,20 @@ export async function onTimer(state: CronServiceState) {
           : DEFAULT_JOB_TIMEOUT_MS;
 
       try {
+        const runAbortController =
+          typeof jobTimeoutMs === "number" ? new AbortController() : undefined;
         const result =
           typeof jobTimeoutMs === "number"
             ? await (async () => {
                 let timeoutId: NodeJS.Timeout | undefined;
                 try {
                   return await Promise.race([
-                    executeJobCore(state, job),
+                    executeJobCore(state, job, runAbortController?.signal),
                     new Promise<never>((_, reject) => {
-                      timeoutId = setTimeout(
-                        () => reject(new Error("cron: job execution timed out")),
-                        jobTimeoutMs,
-                      );
+                      timeoutId = setTimeout(() => {
+                        runAbortController?.abort(new Error("cron: job execution timed out"));
+                        reject(new Error("cron: job execution timed out"));
+                      }, jobTimeoutMs);
                     }),
                   ]);
                 } finally {
@@ -565,6 +567,7 @@ export async function runDueJobs(state: CronServiceState) {
 async function executeJobCore(
   state: CronServiceState,
   job: CronJob,
+  abortSignal?: AbortSignal,
 ): Promise<CronRunOutcome & CronRunTelemetry & { delivered?: boolean }> {
   if (job.sessionTarget === "main") {
     const text = resolveJobPayloadTextForMain(job);
@@ -634,10 +637,14 @@ async function executeJobCore(
   if (job.payload.kind !== "agentTurn") {
     return { status: "skipped", error: "isolated job requires payload.kind=agentTurn" };
   }
+  if (abortSignal?.aborted) {
+    return { status: "error", error: "cron: job execution aborted" };
+  }
 
   const res = await state.deps.runIsolatedAgentJob({
     job,
     message: job.payload.message,
+    abortSignal,
   });
 
   // Post a short summary back to the main session — but only when the
diff --git a/src/gateway/server-cron.ts b/src/gateway/server-cron.ts
index b681377b13c..b0b2de28cac 100644
--- a/src/gateway/server-cron.ts
+++ b/src/gateway/server-cron.ts
@@ -185,13 +185,14 @@ export function buildGatewayCronService(params: {
         deps: { ...params.deps, runtime: defaultRuntime },
       });
     },
-    runIsolatedAgentJob: async ({ job, message }) => {
+    runIsolatedAgentJob: async ({ job, message, abortSignal }) => {
       const { agentId, cfg: runtimeConfig } = resolveCronAgent(job.agentId);
       return await runCronIsolatedAgentTurn({
         cfg: runtimeConfig,
         deps: params.deps,
         job,
         message,
+        abortSignal,
         agentId,
         sessionKey: `cron:${job.id}`,
         lane: "cron",
diff --git a/src/infra/provider-usage.fetch.claude.test.ts b/src/infra/provider-usage.fetch.claude.test.ts
index b8fbaffb71c..7650a8e8c87 100644
--- a/src/infra/provider-usage.fetch.claude.test.ts
+++ b/src/infra/provider-usage.fetch.claude.test.ts
@@ -107,7 +107,7 @@ describe("fetchClaudeUsage", () => {
     expect(result.windows).toEqual([{ label: "5h", usedPercent: 12, resetAt: undefined }]);
   });
 
-  it("keeps oauth error when cookie header cannot be parsed into a session key", async () => {
+  it("parses sessionKey from CLAUDE_WEB_COOKIE for web fallback", async () => {
     vi.stubEnv("CLAUDE_WEB_COOKIE", "sessionKey=sk-ant-cookie-session");
 
     const mockFetch = createScopeFallbackFetch(async (url) => {
@@ -120,7 +120,10 @@ describe("fetchClaudeUsage", () => {
       return makeResponse(404, "not found");
     });
 
-    await expectMissingScopeWithoutFallback(mockFetch);
+    const result = await fetchClaudeUsage("token", 5000, mockFetch);
+    expect(result.error).toBeUndefined();
+    expect(result.windows).toEqual([{ label: "Opus", usedPercent: 44 }]);
+    expect(mockFetch).toHaveBeenCalledTimes(3);
   });
 
   it("keeps oauth error when fallback session key is unavailable", async () => {
diff --git a/src/infra/provider-usage.fetch.claude.ts b/src/infra/provider-usage.fetch.claude.ts
index 927c76e4c0b..41ffcb37b20 100644
--- a/src/infra/provider-usage.fetch.claude.ts
+++ b/src/infra/provider-usage.fetch.claude.ts
@@ -57,8 +57,8 @@ function resolveClaudeWebSessionKey(): string | undefined {
   if (!cookieHeader) {
     return undefined;
   }
-  const stripped = cookieHeader.replace(/^cookie:\\s*/i, "");
-  const match = stripped.match(/(?:^|;\\s*)sessionKey=([^;\\s]+)/i);
+  const stripped = cookieHeader.replace(/^cookie:\s*/i, "");
+  const match = stripped.match(/(?:^|;\s*)sessionKey=([^;\s]+)/i);
   const value = match?.[1]?.trim();
   return value?.startsWith("sk-ant-") ? value : undefined;
 }
diff --git a/src/signal/daemon.ts b/src/signal/daemon.ts
index cc99f6ca37a..e85eb0021fa 100644
--- a/src/signal/daemon.ts
+++ b/src/signal/daemon.ts
@@ -16,6 +16,8 @@ export type SignalDaemonOpts = {
 export type SignalDaemonHandle = {
   pid?: number;
   stop: () => void;
+  exited: Promise<{ code: number | null; signal: NodeJS.Signals | null }>;
+  isExited: () => boolean;
 };
 
 export function classifySignalCliLogLine(line: string): "log" | "error" | null {
@@ -83,17 +85,51 @@ export function spawnSignalDaemon(opts: SignalDaemonOpts): SignalDaemonHandle {
   });
   const log = opts.runtime?.log ?? (() => {});
   const error = opts.runtime?.error ?? (() => {});
+  let exited = false;
+  let settledExit = false;
+  let resolveExit!: (value: { code: number | null; signal: NodeJS.Signals | null }) => void;
+  const exitedPromise = new Promise<{ code: number | null; signal: NodeJS.Signals | null }>(
+    (resolve) => {
+      resolveExit = resolve;
+    },
+  );
+  const settleExit = (value: { code: number | null; signal: NodeJS.Signals | null }) => {
+    if (settledExit) {
+      return;
+    }
+    settledExit = true;
+    exited = true;
+    resolveExit(value);
+  };
 
   bindSignalCliOutput({ stream: child.stdout, log, error });
   bindSignalCliOutput({ stream: child.stderr, log, error });
+  child.once("exit", (code, signal) => {
+    settleExit({
+      code: typeof code === "number" ? code : null,
+      signal: signal ?? null,
+    });
+    error(
+      `signal-cli daemon exited (code=${String(code ?? "null")} signal=${String(signal ?? "null")})`,
+    );
+  });
+  child.once("close", (code, signal) => {
+    settleExit({
+      code: typeof code === "number" ? code : null,
+      signal: signal ?? null,
+    });
+  });
   child.on("error", (err) => {
     error(`signal-cli spawn error: ${String(err)}`);
+    settleExit({ code: null, signal: null });
   });
 
   return {
     pid: child.pid ?? undefined,
+    exited: exitedPromise,
+    isExited: () => exited,
     stop: () => {
-      if (!child.killed) {
+      if (!child.killed && !exited) {
         child.kill("SIGTERM");
       }
     },
diff --git a/src/signal/monitor.tool-result.sends-tool-summaries-responseprefix.test.ts b/src/signal/monitor.tool-result.sends-tool-summaries-responseprefix.test.ts
index f21d2230324..6cbaf96623b 100644
--- a/src/signal/monitor.tool-result.sends-tool-summaries-responseprefix.test.ts
+++ b/src/signal/monitor.tool-result.sends-tool-summaries-responseprefix.test.ts
@@ -23,6 +23,7 @@ const {
   updateLastRouteMock,
   upsertPairingRequestMock,
   waitForTransportReadyMock,
+  spawnSignalDaemonMock,
 } = getSignalToolResultTestMocks();
 
 const SIGNAL_BASE_URL = "http://127.0.0.1:8080";
@@ -176,7 +177,7 @@ describe("monitorSignalProvider tool results", () => {
         logIntervalMs: 10_000,
         pollIntervalMs: 150,
         runtime,
-        abortSignal: abortController.signal,
+        abortSignal: expect.any(AbortSignal),
       }),
     );
   });
@@ -212,6 +213,39 @@ describe("monitorSignalProvider tool results", () => {
     expectWaitForTransportReadyTimeout(120_000);
   });
 
+  it("fails fast when auto-started signal daemon exits during startup", async () => {
+    const runtime = createMonitorRuntime();
+    setSignalAutoStartConfig();
+    spawnSignalDaemonMock.mockReturnValueOnce({
+      stop: vi.fn(),
+      exited: Promise.resolve({ code: 1, signal: null }),
+      isExited: () => true,
+    });
+    waitForTransportReadyMock.mockImplementationOnce(
+      async (params: { abortSignal?: AbortSignal | null }) => {
+        await new Promise<void>((_resolve, reject) => {
+          if (params.abortSignal?.aborted) {
+            reject(params.abortSignal.reason);
+            return;
+          }
+          params.abortSignal?.addEventListener(
+            "abort",
+            () => reject(params.abortSignal?.reason ?? new Error("aborted")),
+            { once: true },
+          );
+        });
+      },
+    );
+
+    await expect(
+      runMonitorWithMocks({
+        autoStart: true,
+        baseUrl: SIGNAL_BASE_URL,
+        runtime,
+      }),
+    ).rejects.toThrow(/signal daemon exited/i);
+  });
+
   it("skips tool summaries with responsePrefix", async () => {
     replyMock.mockResolvedValue({ text: "final reply" });
 
diff --git a/src/signal/monitor.tool-result.test-harness.ts b/src/signal/monitor.tool-result.test-harness.ts
index 7d1919c5bb4..e05ebe94f5f 100644
--- a/src/signal/monitor.tool-result.test-harness.ts
+++ b/src/signal/monitor.tool-result.test-harness.ts
@@ -13,6 +13,7 @@ type SignalToolResultTestMocks = {
   streamMock: MockFn;
   signalCheckMock: MockFn;
   signalRpcRequestMock: MockFn;
+  spawnSignalDaemonMock: MockFn;
 };
 
 const waitForTransportReadyMock = vi.hoisted(() => vi.fn()) as unknown as MockFn;
@@ -24,6 +25,7 @@ const upsertPairingRequestMock = vi.hoisted(() => vi.fn()) as unknown as MockFn;
 const streamMock = vi.hoisted(() => vi.fn()) as unknown as MockFn;
 const signalCheckMock = vi.hoisted(() => vi.fn()) as unknown as MockFn;
 const signalRpcRequestMock = vi.hoisted(() => vi.fn()) as unknown as MockFn;
+const spawnSignalDaemonMock = vi.hoisted(() => vi.fn()) as unknown as MockFn;
 
 export function getSignalToolResultTestMocks(): SignalToolResultTestMocks {
   return {
@@ -36,6 +38,7 @@ export function getSignalToolResultTestMocks(): SignalToolResultTestMocks {
     streamMock,
     signalCheckMock,
     signalRpcRequestMock,
+    spawnSignalDaemonMock,
   };
 }
 
@@ -84,7 +87,7 @@ vi.mock("./client.js", () => ({
 }));
 
 vi.mock("./daemon.js", () => ({
-  spawnSignalDaemon: vi.fn(() => ({ stop: vi.fn() })),
+  spawnSignalDaemon: (...args: unknown[]) => spawnSignalDaemonMock(...args),
 }));
 
 vi.mock("../infra/transport-ready.js", () => ({
@@ -107,6 +110,11 @@ export function installSignalToolResultTestHooks() {
     streamMock.mockReset();
     signalCheckMock.mockReset().mockResolvedValue({});
     signalRpcRequestMock.mockReset().mockResolvedValue({});
+    spawnSignalDaemonMock.mockReset().mockReturnValue({
+      stop: vi.fn(),
+      exited: new Promise(() => {}),
+      isExited: () => false,
+    });
     readAllowFromStoreMock.mockReset().mockResolvedValue([]);
     upsertPairingRequestMock.mockReset().mockResolvedValue({ code: "PAIRCODE", created: true });
     waitForTransportReadyMock.mockReset().mockResolvedValue(undefined);
diff --git a/src/signal/monitor.ts b/src/signal/monitor.ts
index baf45795c19..0bcff74b795 100644
--- a/src/signal/monitor.ts
+++ b/src/signal/monitor.ts
@@ -47,6 +47,46 @@ function resolveRuntime(opts: MonitorSignalOpts): RuntimeEnv {
   return opts.runtime ?? createNonExitingRuntime();
 }
 
+function mergeAbortSignals(
+  a?: AbortSignal,
+  b?: AbortSignal,
+): { signal?: AbortSignal; dispose: () => void } {
+  if (!a && !b) {
+    return { signal: undefined, dispose: () => {} };
+  }
+  if (!a) {
+    return { signal: b, dispose: () => {} };
+  }
+  if (!b) {
+    return { signal: a, dispose: () => {} };
+  }
+  const controller = new AbortController();
+  const abortFrom = (source: AbortSignal) => {
+    if (!controller.signal.aborted) {
+      controller.abort(source.reason);
+    }
+  };
+  if (a.aborted) {
+    abortFrom(a);
+    return { signal: controller.signal, dispose: () => {} };
+  }
+  if (b.aborted) {
+    abortFrom(b);
+    return { signal: controller.signal, dispose: () => {} };
+  }
+  const onAbortA = () => abortFrom(a);
+  const onAbortB = () => abortFrom(b);
+  a.addEventListener("abort", onAbortA, { once: true });
+  b.addEventListener("abort", onAbortB, { once: true });
+  return {
+    signal: controller.signal,
+    dispose: () => {
+      a.removeEventListener("abort", onAbortA);
+      b.removeEventListener("abort", onAbortB);
+    },
+  };
+}
+
 function normalizeAllowList(raw?: Array<string | number>): string[] {
   return normalizeStringEntries(raw);
 }
@@ -286,6 +326,9 @@ export async function monitorSignalProvider(opts: MonitorSignalOpts = {}): Promi
     Math.max(1_000, opts.startupTimeoutMs ?? accountInfo.config.startupTimeoutMs ?? 30_000),
   );
   const readReceiptsViaDaemon = Boolean(autoStart && sendReadReceipts);
+  let daemonExitError: Error | undefined;
+  const daemonAbortController = new AbortController();
+  const mergedAbort = mergeAbortSignals(opts.abortSignal, daemonAbortController.signal);
   let daemonHandle: ReturnType<typeof spawnSignalDaemon> | null = null;
 
   if (autoStart) {
@@ -303,6 +346,14 @@ export async function monitorSignalProvider(opts: MonitorSignalOpts = {}): Promi
       sendReadReceipts,
       runtime,
     });
+    void daemonHandle.exited.then((exit) => {
+      daemonExitError = new Error(
+        `signal daemon exited (code=${String(exit.code ?? "null")} signal=${String(exit.signal ?? "null")})`,
+      );
+      if (!daemonAbortController.signal.aborted) {
+        daemonAbortController.abort(daemonExitError);
+      }
+    });
   }
 
   const onAbort = () => {
@@ -314,12 +365,15 @@ export async function monitorSignalProvider(opts: MonitorSignalOpts = {}): Promi
     if (daemonHandle) {
       await waitForSignalDaemonReady({
         baseUrl,
-        abortSignal: opts.abortSignal,
+        abortSignal: mergedAbort.signal,
         timeoutMs: startupTimeoutMs,
         logAfterMs: 10_000,
         logIntervalMs: 10_000,
         runtime,
       });
+      if (daemonExitError) {
+        throw daemonExitError;
+      }
     }
 
     const handleEvent = createSignalEventHandler({
@@ -353,7 +407,7 @@ export async function monitorSignalProvider(opts: MonitorSignalOpts = {}): Promi
     await runSignalSseLoop({
       baseUrl,
       account,
-      abortSignal: opts.abortSignal,
+      abortSignal: mergedAbort.signal,
       runtime,
       onEvent: (event) => {
         void handleEvent(event).catch((err) => {
@@ -361,12 +415,16 @@ export async function monitorSignalProvider(opts: MonitorSignalOpts = {}): Promi
         });
       },
     });
+    if (daemonExitError) {
+      throw daemonExitError;
+    }
   } catch (err) {
-    if (opts.abortSignal?.aborted) {
+    if (opts.abortSignal?.aborted && !daemonExitError) {
       return;
     }
     throw err;
   } finally {
+    mergedAbort.dispose();
     opts.abortSignal?.removeEventListener("abort", onAbort);
     daemonHandle?.stop();
   }
diff --git a/src/web/auto-reply/deliver-reply.test.ts b/src/web/auto-reply/deliver-reply.test.ts
index ff5f7b6f100..385fcd65af7 100644
--- a/src/web/auto-reply/deliver-reply.test.ts
+++ b/src/web/auto-reply/deliver-reply.test.ts
@@ -98,6 +98,28 @@ describe("deliverWebReply", () => {
     expect(sleep).toHaveBeenCalledWith(500);
   });
 
+  it("retries text send when error contains timed out", async () => {
+    const msg = makeMsg();
+    (msg.reply as unknown as { mockRejectedValueOnce: (v: unknown) => void }).mockRejectedValueOnce(
+      new Error("operation timed out"),
+    );
+    (msg.reply as unknown as { mockResolvedValueOnce: (v: unknown) => void }).mockResolvedValueOnce(
+      undefined,
+    );
+
+    await deliverWebReply({
+      replyResult: { text: "hi" },
+      msg,
+      maxMediaBytes: 1024 * 1024,
+      textLimit: 200,
+      replyLogger,
+      skipLog: true,
+    });
+
+    expect(msg.reply).toHaveBeenCalledTimes(2);
+    expect(sleep).toHaveBeenCalledWith(500);
+  });
+
   it("sends image media with caption and then remaining text", async () => {
     const msg = makeMsg();
     const mediaLocalRoots = ["/tmp/workspace-work"];
diff --git a/src/web/auto-reply/deliver-reply.ts b/src/web/auto-reply/deliver-reply.ts
index cb9b1e6ed44..664e8acee85 100644
--- a/src/web/auto-reply/deliver-reply.ts
+++ b/src/web/auto-reply/deliver-reply.ts
@@ -50,7 +50,7 @@ export async function deliverWebReply(params: {
         lastErr = err;
         const errText = formatError(err);
         const isLast = attempt === maxAttempts;
-        const shouldRetry = /closed|reset|timed\\s*out|disconnect/i.test(errText);
+        const shouldRetry = /closed|reset|timed\s*out|disconnect/i.test(errText);
         if (!shouldRetry || isLast) {
           throw err;
         }