diff --git a/CHANGELOG.md b/CHANGELOG.md
index cf9e30958..40bda8949 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -24,6 +24,7 @@ Docs: https://docs.openclaw.ai
 - Cron/announce delivery robustness: bypass pending-descendant announce guards for cron completion sends, ensure named-agent announce routes have outbound session entries, and fall back to direct delivery only when an announce send was actually attempted and failed. (from #35185, #32443, #34987) Thanks @Sid-Qin, @scoootscooob, and @bmendonca3.
 - Auto-reply/system events: restore runtime system events to the message timeline (`System:` lines), preserve think-hint parsing with prepended events, and carry events into deferred followup/collect/steer-backlog prompts to keep cache behavior stable without dropping queued metadata. (#34794) Thanks @anisoptera.
 - Security/audit account handling: avoid prototype-chain account IDs in audit validation by using own-property checks for `accounts`. (#34982) Thanks @HOYALIM.
+- Cron/restart catch-up semantics: replay interrupted recurring jobs and missed immediate cron slots on startup without replaying interrupted one-shot jobs, with guarded missed-slot probing to avoid malformed-schedule startup aborts and duplicate-trigger drift after restart. (from #34466, #34896, #34625, #33206) Thanks @dunamismax, @dsantoreis, @Octane0411, and @Sid-Qin.
 - Agents/session usage tracking: preserve accumulated usage metadata on embedded Pi runner error exits so failed turns still update session `totalTokens` from real usage instead of stale prior values. (#34275) thanks @RealKai42.
 - Nodes/system.run approval hardening: use explicit argv-mutation signaling when regenerating prepared `rawCommand`, and cover the `system.run.prepare -> system.run` handoff so direct PATH-based `nodes.run` commands no longer fail with `rawCommand does not match command`. (#33137) thanks @Sid-Qin.
 - Models/custom provider headers: propagate `models.providers.<name>.headers` across inline, fallback, and registry-found model resolution so header-authenticated proxies consistently receive configured request headers. (#27490) thanks @Sid-Qin.
diff --git a/src/cron/schedule.test.ts b/src/cron/schedule.test.ts
index 6b6c290b3..614a980f4 100644
--- a/src/cron/schedule.test.ts
+++ b/src/cron/schedule.test.ts
@@ -2,6 +2,7 @@ import { beforeEach, describe, expect, it } from "vitest";
 import {
   clearCronScheduleCacheForTest,
   computeNextRunAtMs,
+  computePreviousRunAtMs,
   getCronScheduleCacheSizeForTest,
 } from "./schedule.js";
 
@@ -91,6 +92,17 @@ describe("cron schedule", () => {
     expect(next!).toBeGreaterThan(nowMs);
   });
 
+  it("never returns a previous run that is at-or-after now", () => {
+    const nowMs = Date.parse("2026-03-01T00:00:00.000Z");
+    const previous = computePreviousRunAtMs(
+      { kind: "cron", expr: "0 8 * * *", tz: "Asia/Shanghai" },
+      nowMs,
+    );
+    if (previous !== undefined) {
+      expect(previous).toBeLessThan(nowMs);
+    }
+  });
+
   it("reuses compiled cron evaluators for the same expression/timezone", () => {
     const nowMs = Date.parse("2026-03-01T00:00:00.000Z");
     expect(getCronScheduleCacheSizeForTest()).toBe(0);
diff --git a/src/cron/schedule.ts b/src/cron/schedule.ts
index 70577b761..4c31c0a1a 100644
--- a/src/cron/schedule.ts
+++ b/src/cron/schedule.ts
@@ -108,6 +108,35 @@ export function computeNextRunAtMs(schedule: CronSchedule, nowMs: number): numbe
   return nextMs;
 }
 
+export function computePreviousRunAtMs(schedule: CronSchedule, nowMs: number): number | undefined {
+  if (schedule.kind !== "cron") {
+    return undefined;
+  }
+  const cronSchedule = schedule as { expr?: unknown; cron?: unknown };
+  const exprSource = typeof cronSchedule.expr === "string" ? cronSchedule.expr : cronSchedule.cron;
+  if (typeof exprSource !== "string") {
+    throw new Error("invalid cron schedule: expr is required");
+  }
+  const expr = exprSource.trim();
+  if (!expr) {
+    return undefined;
+  }
+  const cron = resolveCachedCron(expr, resolveCronTimezone(schedule.tz));
+  const previousRuns = cron.previousRuns(1, new Date(nowMs));
+  const previous = previousRuns[0];
+  if (!previous) {
+    return undefined;
+  }
+  const previousMs = previous.getTime();
+  if (!Number.isFinite(previousMs)) {
+    return undefined;
+  }
+  if (previousMs >= nowMs) {
+    return undefined;
+  }
+  return previousMs;
+}
+
 export function clearCronScheduleCacheForTest(): void {
   cronEvalCache.clear();
 }
diff --git a/src/cron/service.restart-catchup.test.ts b/src/cron/service.restart-catchup.test.ts
index ea42e7b5a..9c833a994 100644
--- a/src/cron/service.restart-catchup.test.ts
+++ b/src/cron/service.restart-catchup.test.ts
@@ -128,6 +128,179 @@ describe("CronService restart catch-up", () => {
     expect(updated?.state.lastRunAtMs).toBeUndefined();
     expect((updated?.state.nextRunAtMs ?? 0) > Date.parse("2025-12-13T17:00:00.000Z")).toBe(true);
 
+    cron.stop();
+    await store.cleanup();
+  });
+  it("replays the most recent missed cron slot after restart when nextRunAtMs already advanced", async () => {
+    vi.setSystemTime(new Date("2025-12-13T04:02:00.000Z"));
+    const store = await makeStorePath();
+    const enqueueSystemEvent = vi.fn();
+    const requestHeartbeatNow = vi.fn();
+
+    await writeStoreJobs(store.storePath, [
+      {
+        id: "restart-missed-slot",
+        name: "every ten minutes +1",
+        enabled: true,
+        createdAtMs: Date.parse("2025-12-10T12:00:00.000Z"),
+        updatedAtMs: Date.parse("2025-12-13T04:01:00.000Z"),
+        schedule: { kind: "cron", expr: "1,11,21,31,41,51 4-20 * * *", tz: "UTC" },
+        sessionTarget: "main",
+        wakeMode: "next-heartbeat",
+        payload: { kind: "systemEvent", text: "catch missed slot" },
+        state: {
+          // Persisted state may already be recomputed from restart time and
+          // point to the future slot, even though 04:01 was missed.
+          nextRunAtMs: Date.parse("2025-12-13T04:11:00.000Z"),
+          lastRunAtMs: Date.parse("2025-12-13T03:51:00.000Z"),
+          lastStatus: "ok",
+        },
+      },
+    ]);
+
+    const cron = createRestartCronService({
+      storePath: store.storePath,
+      enqueueSystemEvent,
+      requestHeartbeatNow,
+    });
+
+    await cron.start();
+
+    expect(enqueueSystemEvent).toHaveBeenCalledWith(
+      "catch missed slot",
+      expect.objectContaining({ agentId: undefined }),
+    );
+    expect(requestHeartbeatNow).toHaveBeenCalled();
+
+    const jobs = await cron.list({ includeDisabled: true });
+    const updated = jobs.find((job) => job.id === "restart-missed-slot");
+    expect(updated?.state.lastRunAtMs).toBe(Date.parse("2025-12-13T04:02:00.000Z"));
+
+    cron.stop();
+    await store.cleanup();
+  });
+
+  it("does not replay interrupted one-shot jobs on startup", async () => {
+    const store = await makeStorePath();
+    const enqueueSystemEvent = vi.fn();
+    const requestHeartbeatNow = vi.fn();
+
+    const dueAt = Date.parse("2025-12-13T16:00:00.000Z");
+    const staleRunningAt = Date.parse("2025-12-13T16:30:00.000Z");
+
+    await writeStoreJobs(store.storePath, [
+      {
+        id: "restart-stale-one-shot",
+        name: "one shot stale marker",
+        enabled: true,
+        createdAtMs: Date.parse("2025-12-10T12:00:00.000Z"),
+        updatedAtMs: Date.parse("2025-12-13T16:30:00.000Z"),
+        schedule: { kind: "at", at: "2025-12-13T16:00:00.000Z" },
+        sessionTarget: "main",
+        wakeMode: "next-heartbeat",
+        payload: { kind: "systemEvent", text: "one-shot stale marker" },
+        state: {
+          nextRunAtMs: dueAt,
+          runningAtMs: staleRunningAt,
+        },
+      },
+    ]);
+
+    const cron = createRestartCronService({
+      storePath: store.storePath,
+      enqueueSystemEvent,
+      requestHeartbeatNow,
+    });
+
+    await cron.start();
+
+    expect(enqueueSystemEvent).not.toHaveBeenCalled();
+    expect(requestHeartbeatNow).not.toHaveBeenCalled();
+
+    const jobs = await cron.list({ includeDisabled: true });
+    const updated = jobs.find((job) => job.id === "restart-stale-one-shot");
+    expect(updated?.state.runningAtMs).toBeUndefined();
+
+    cron.stop();
+    await store.cleanup();
+  });
+
+  it("does not replay cron slot when the latest slot already ran before restart", async () => {
+    vi.setSystemTime(new Date("2025-12-13T04:02:00.000Z"));
+    const store = await makeStorePath();
+    const enqueueSystemEvent = vi.fn();
+    const requestHeartbeatNow = vi.fn();
+
+    await writeStoreJobs(store.storePath, [
+      {
+        id: "restart-no-duplicate-slot",
+        name: "every ten minutes +1 no duplicate",
+        enabled: true,
+        createdAtMs: Date.parse("2025-12-10T12:00:00.000Z"),
+        updatedAtMs: Date.parse("2025-12-13T04:01:00.000Z"),
+        schedule: { kind: "cron", expr: "1,11,21,31,41,51 4-20 * * *", tz: "UTC" },
+        sessionTarget: "main",
+        wakeMode: "next-heartbeat",
+        payload: { kind: "systemEvent", text: "already ran" },
+        state: {
+          nextRunAtMs: Date.parse("2025-12-13T04:11:00.000Z"),
+          lastRunAtMs: Date.parse("2025-12-13T04:01:00.000Z"),
+          lastStatus: "ok",
+        },
+      },
+    ]);
+
+    const cron = createRestartCronService({
+      storePath: store.storePath,
+      enqueueSystemEvent,
+      requestHeartbeatNow,
+    });
+
+    await cron.start();
+
+    expect(enqueueSystemEvent).not.toHaveBeenCalled();
+    expect(requestHeartbeatNow).not.toHaveBeenCalled();
+    cron.stop();
+    await store.cleanup();
+  });
+
+  it("does not replay missed cron slots while error backoff is pending after restart", async () => {
+    vi.setSystemTime(new Date("2025-12-13T04:02:00.000Z"));
+    const store = await makeStorePath();
+    const enqueueSystemEvent = vi.fn();
+    const requestHeartbeatNow = vi.fn();
+
+    await writeStoreJobs(store.storePath, [
+      {
+        id: "restart-backoff-pending",
+        name: "backoff pending",
+        enabled: true,
+        createdAtMs: Date.parse("2025-12-10T12:00:00.000Z"),
+        updatedAtMs: Date.parse("2025-12-13T04:01:10.000Z"),
+        schedule: { kind: "cron", expr: "* * * * *", tz: "UTC" },
+        sessionTarget: "main",
+        wakeMode: "next-heartbeat",
+        payload: { kind: "systemEvent", text: "do not run during backoff" },
+        state: {
+          // Next retry is intentionally delayed by backoff despite a newer cron slot.
+          nextRunAtMs: Date.parse("2025-12-13T04:10:00.000Z"),
+          lastRunAtMs: Date.parse("2025-12-13T04:01:00.000Z"),
+          lastStatus: "error",
+        },
+      },
+    ]);
+
+    const cron = createRestartCronService({
+      storePath: store.storePath,
+      enqueueSystemEvent,
+      requestHeartbeatNow,
+    });
+
+    await cron.start();
+
+    expect(enqueueSystemEvent).not.toHaveBeenCalled();
+    expect(requestHeartbeatNow).not.toHaveBeenCalled();
+
     cron.stop();
     await store.cleanup();
   });
diff --git a/src/cron/service/jobs.ts b/src/cron/service/jobs.ts
index d0d0befb6..6ae2e1304 100644
--- a/src/cron/service/jobs.ts
+++ b/src/cron/service/jobs.ts
@@ -1,7 +1,7 @@
 import crypto from "node:crypto";
 import { normalizeAgentId } from "../../routing/session-key.js";
 import { parseAbsoluteTimeMs } from "../parse.js";
-import { computeNextRunAtMs } from "../schedule.js";
+import { computeNextRunAtMs, computePreviousRunAtMs } from "../schedule.js";
 import {
   normalizeCronStaggerMs,
   resolveCronStaggerMs,
@@ -80,6 +80,34 @@ function computeStaggeredCronNextRunAtMs(job: CronJob, nowMs: number) {
   return undefined;
 }
 
+function computeStaggeredCronPreviousRunAtMs(job: CronJob, nowMs: number) {
+  if (job.schedule.kind !== "cron") {
+    return undefined;
+  }
+
+  const staggerMs = resolveCronStaggerMs(job.schedule);
+  const offsetMs = resolveStableCronOffsetMs(job.id, staggerMs);
+  if (offsetMs <= 0) {
+    return computePreviousRunAtMs(job.schedule, nowMs);
+  }
+
+  // Shift the cursor backwards by the same per-job offset used for next-run
+  // math so previous-run lookup matches the effective staggered schedule.
+  let cursorMs = Math.max(0, nowMs - offsetMs);
+  for (let attempt = 0; attempt < 4; attempt += 1) {
+    const basePrevious = computePreviousRunAtMs(job.schedule, cursorMs);
+    if (basePrevious === undefined) {
+      return undefined;
+    }
+    const shifted = basePrevious + offsetMs;
+    if (shifted <= nowMs) {
+      return shifted;
+    }
+    cursorMs = Math.max(0, basePrevious - 1_000);
+  }
+  return undefined;
+}
+
 function isFiniteTimestamp(value: unknown): value is number {
   return typeof value === "number" && Number.isFinite(value);
 }
@@ -248,6 +276,14 @@ export function computeJobNextRunAtMs(job: CronJob, nowMs: number): number | und
   return isFiniteTimestamp(next) ? next : undefined;
 }
 
+export function computeJobPreviousRunAtMs(job: CronJob, nowMs: number): number | undefined {
+  if (!job.enabled || job.schedule.kind !== "cron") {
+    return undefined;
+  }
+  const previous = computeStaggeredCronPreviousRunAtMs(job, nowMs);
+  return isFiniteTimestamp(previous) ? previous : undefined;
+}
+
 /** Maximum consecutive schedule errors before auto-disabling a job. */
 const MAX_SCHEDULE_ERRORS = 3;
 
diff --git a/src/cron/service/timer.ts b/src/cron/service/timer.ts
index ec9d919ec..081e94084 100644
--- a/src/cron/service/timer.ts
+++ b/src/cron/service/timer.ts
@@ -14,6 +14,7 @@ import type {
   CronRunTelemetry,
 } from "../types.js";
 import {
+  computeJobPreviousRunAtMs,
   computeJobNextRunAtMs,
   nextWakeAtMs,
   recomputeNextRunsForMaintenance,
@@ -700,6 +701,7 @@ function isRunnableJob(params: {
   nowMs: number;
   skipJobIds?: ReadonlySet<string>;
   skipAtIfAlreadyRan?: boolean;
+  allowCronMissedRunByLastRun?: boolean;
 }): boolean {
   const { job, nowMs } = params;
   if (!job.state) {
@@ -732,13 +734,46 @@ function isRunnableJob(params: {
     return false;
   }
   const next = job.state.nextRunAtMs;
-  return typeof next === "number" && Number.isFinite(next) && nowMs >= next;
+  if (typeof next === "number" && Number.isFinite(next) && nowMs >= next) {
+    return true;
+  }
+  if (
+    typeof next === "number" &&
+    Number.isFinite(next) &&
+    next > nowMs &&
+    job.state.lastStatus === "error"
+  ) {
+    // Respect persisted retry backoff windows for recurring jobs on restart.
+    return false;
+  }
+  if (!params.allowCronMissedRunByLastRun || job.schedule.kind !== "cron") {
+    return false;
+  }
+  let previousRunAtMs: number | undefined;
+  try {
+    previousRunAtMs = computeJobPreviousRunAtMs(job, nowMs);
+  } catch {
+    return false;
+  }
+  if (typeof previousRunAtMs !== "number" || !Number.isFinite(previousRunAtMs)) {
+    return false;
+  }
+  const lastRunAtMs = job.state.lastRunAtMs;
+  if (typeof lastRunAtMs !== "number" || !Number.isFinite(lastRunAtMs)) {
+    // Only replay a "missed slot" when there is concrete run history.
+    return false;
+  }
+  return previousRunAtMs > lastRunAtMs;
 }
 
 function collectRunnableJobs(
   state: CronServiceState,
   nowMs: number,
-  opts?: { skipJobIds?: ReadonlySet<string>; skipAtIfAlreadyRan?: boolean },
+  opts?: {
+    skipJobIds?: ReadonlySet<string>;
+    skipAtIfAlreadyRan?: boolean;
+    allowCronMissedRunByLastRun?: boolean;
+  },
 ): CronJob[] {
   if (!state.store) {
     return [];
@@ -749,6 +784,7 @@ function collectRunnableJobs(
       nowMs,
       skipJobIds: opts?.skipJobIds,
       skipAtIfAlreadyRan: opts?.skipAtIfAlreadyRan,
+      allowCronMissedRunByLastRun: opts?.allowCronMissedRunByLastRun,
     }),
   );
 }
@@ -764,7 +800,11 @@ export async function runMissedJobs(
     }
     const now = state.deps.nowMs();
     const skipJobIds = opts?.skipJobIds;
-    const missed = collectRunnableJobs(state, now, { skipJobIds, skipAtIfAlreadyRan: true });
+    const missed = collectRunnableJobs(state, now, {
+      skipJobIds,
+      skipAtIfAlreadyRan: true,
+      allowCronMissedRunByLastRun: true,
+    });
     if (missed.length === 0) {
       return [] as Array<{ jobId: string; job: CronJob }>;
     }