diff --git a/src/cron/service/timeout-policy.test.ts b/src/cron/service/timeout-policy.test.ts
index 69ca6aa46c3..8aae440f505 100644
--- a/src/cron/service/timeout-policy.test.ts
+++ b/src/cron/service/timeout-policy.test.ts
@@ -23,11 +23,30 @@ function makeJob(payload: CronJob["payload"]): CronJob {
 }
 
 describe("timeout-policy", () => {
-  it("uses default timeout for non-agent jobs", () => {
+  it("uses default timeout for systemEvent jobs with wakeMode=next-heartbeat", () => {
     const timeout = resolveCronJobTimeoutMs(makeJob({ kind: "systemEvent", text: "hello" }));
     expect(timeout).toBe(DEFAULT_JOB_TIMEOUT_MS);
   });
 
+  it("uses expanded safety timeout for systemEvent jobs targeting main with wakeMode=now", () => {
+    // wakeMode="now" + sessionTarget="main" blocks until the full agent turn completes
+    // via runHeartbeatOnce(), so it needs the same generous ceiling as agentTurn jobs.
+    const job: CronJob = {
+      id: "job-1",
+      name: "job",
+      createdAtMs: 0,
+      updatedAtMs: 0,
+      enabled: true,
+      schedule: { kind: "every", everyMs: 60_000 },
+      sessionTarget: "main",
+      wakeMode: "now",
+      payload: { kind: "systemEvent", text: "check in" },
+      state: {},
+    };
+    const timeout = resolveCronJobTimeoutMs(job);
+    expect(timeout).toBe(AGENT_TURN_SAFETY_TIMEOUT_MS);
+  });
+
   it("uses expanded safety timeout for agentTurn jobs without explicit timeout", () => {
     const timeout = resolveCronJobTimeoutMs(makeJob({ kind: "agentTurn", message: "hi" }));
     expect(timeout).toBe(AGENT_TURN_SAFETY_TIMEOUT_MS);
diff --git a/src/cron/service/timeout-policy.ts b/src/cron/service/timeout-policy.ts
index 7b03b8bda52..607a8fa8921 100644
--- a/src/cron/service/timeout-policy.ts
+++ b/src/cron/service/timeout-policy.ts
@@ -19,7 +19,25 @@ export function resolveCronJobTimeoutMs(job: CronJob): number | undefined {
       ? Math.floor(job.payload.timeoutSeconds * 1_000)
       : undefined;
   if (configuredTimeoutMs === undefined) {
-    return job.payload.kind === "agentTurn" ? AGENT_TURN_SAFETY_TIMEOUT_MS : DEFAULT_JOB_TIMEOUT_MS;
+    // agentTurn jobs get the large safety ceiling since turns can run for a long time.
+    if (job.payload.kind === "agentTurn") {
+      return AGENT_TURN_SAFETY_TIMEOUT_MS;
+    }
+    // systemEvent jobs targeting "main" with wakeMode="now" call runHeartbeatOnce(),
+    // which blocks until the full agent turn completes. The turn duration is
+    // unbounded, so apply the same generous ceiling as agentTurn jobs instead of
+    // the short DEFAULT_JOB_TIMEOUT_MS that was incorrectly timing out long-running
+    // main-session heartbeats. See: https://github.com/openclaw/openclaw/issues/50621
+    if (
+      job.payload.kind === "systemEvent" &&
+      job.sessionTarget === "main" &&
+      job.wakeMode === "now"
+    ) {
+      return AGENT_TURN_SAFETY_TIMEOUT_MS;
+    }
+    // All other systemEvent jobs (wakeMode !== "now") are fire-and-forget:
+    // they enqueue the event and return immediately, so the short default is fine.
+    return DEFAULT_JOB_TIMEOUT_MS;
   }
   return configuredTimeoutMs <= 0 ? undefined : configuredTimeoutMs;
 }