diff --git a/src/commands/doctor/cron/index.test.ts b/src/commands/doctor/cron/index.test.ts
index 0f41b062d451..a667d5aa7b45 100644
--- a/src/commands/doctor/cron/index.test.ts
+++ b/src/commands/doctor/cron/index.test.ts
@@ -543,6 +543,88 @@ describe("maybeRepairLegacyCronStore", () => {
     });
   });
 
+  describe("chronic failure advisory", () => {
+    it("warns about repeatedly failing jobs without touching the store", async () => {
+      const storePath = await makeTempStorePath();
+      await writeCurrentCronStore(storePath, [
+        createCurrentCronJob({
+          id: "failing-job",
+          state: { lastRunStatus: "error", consecutiveErrors: 5, lastError: "boom" },
+        }),
+      ]);
+      const prompter = makePrompter(true);
+
+      await maybeRepairLegacyCronStore({
+        cfg: createCronConfig(storePath),
+        options: {},
+        prompter,
+      });
+
+      expectNoteContaining("1 cron job has failed 3+ runs in a row", "Cron");
+      expectNoteContaining("re-fires it on error backoff", "Cron");
+      expectNoteContaining("resets on the next successful run", "Cron");
+      expectNoteContaining("interrupted by a gateway restart", "Cron");
+      expectNoteContaining("openclaw cron show <id>", "Cron");
+
+      // Observer-only: no repair prompt and the failure counters stay untouched.
+      expect(prompter.confirm).not.toHaveBeenCalled();
+      const jobs = await readPersistedJobs(storePath);
+      const state = requireRecord(requirePersistedJob(jobs, 0).state, "cron state");
+      expect(state.consecutiveErrors).toBe(5);
+    });
+
+    it("pluralizes and only counts enabled jobs at or above the threshold", async () => {
+      const storePath = await makeTempStorePath();
+      await writeCurrentCronStore(storePath, [
+        createCurrentCronJob({
+          id: "failing-a",
+          state: { lastRunStatus: "error", consecutiveErrors: 3 },
+        }),
+        createCurrentCronJob({
+          id: "failing-b",
+          state: { lastRunStatus: "error", consecutiveErrors: 12 },
+        }),
+        createCurrentCronJob({
+          id: "recovering",
+          state: { lastRunStatus: "error", consecutiveErrors: 2 },
+        }),
+        // Exhausted one-shot jobs get disabled with their error state retained;
+        // they no longer re-fire, so the advisory must not count them.
+        createCurrentCronJob({
+          id: "disabled-exhausted",
+          enabled: false,
+          state: { lastRunStatus: "error", consecutiveErrors: 9 },
+        }),
+      ]);
+
+      await maybeRepairLegacyCronStore({
+        cfg: createCronConfig(storePath),
+        options: {},
+        prompter: makePrompter(true),
+      });
+
+      expectNoteContaining("2 cron jobs have failed 3+ runs in a row", "Cron");
+    });
+
+    it("stays silent when failure streaks are below the threshold", async () => {
+      const storePath = await makeTempStorePath();
+      await writeCurrentCronStore(storePath, [
+        createCurrentCronJob({
+          id: "single-failure",
+          state: { lastRunStatus: "error", consecutiveErrors: 2 },
+        }),
+      ]);
+
+      await maybeRepairLegacyCronStore({
+        cfg: createCronConfig(storePath),
+        options: {},
+        prompter: makePrompter(true),
+      });
+
+      expectNoNoteContaining("runs in a row", "Cron");
+    });
+  });
+
   it("repairs legacy cron store fields and migrates notify fallback to webhook delivery", async () => {
     const storePath = await makeTempStorePath();
     await writeCronStore(storePath, [createLegacyCronJob()]);
diff --git a/src/commands/doctor/cron/index.ts b/src/commands/doctor/cron/index.ts
index 43597b642967..cbc9eb5ac2e4 100644
--- a/src/commands/doctor/cron/index.ts
+++ b/src/commands/doctor/cron/index.ts
@@ -85,6 +85,38 @@ function countInFlightCronJobs(jobs: Array<Record<string, unknown>>): number {
   }).length;
 }
 
+// Fixed advisory threshold: three failures in a row is a clear chronic signal on
+// its own. It coincides with the scheduler's default transient-retry budget, but
+// `cron.retry.maxAttempts` is per-job configurable and doctor deliberately does
+// not mirror retry config or exhaustion semantics (`consecutiveErrors > maxAttempts`).
+const CHRONIC_FAILURE_MIN_CONSECUTIVE_ERRORS = 3;
+
+// Count enabled jobs stuck in repeated run failures. `state.consecutiveErrors`
+// resets to 0 on the next successful run and also increments for runs interrupted
+// by a gateway restart (startup marks in-flight runs failed, `src/cron/service/ops.ts`),
+// so a streak can mean task failures, interrupted runs, or a mix — the note says so.
+// Failure alerts are opt-in, so by default nothing else surfaces the streak.
+// Disabled jobs no longer re-fire (e.g. the scheduler disables exhausted
+// one-shot jobs with their error state retained), so they are excluded.
+function countChronicallyFailingCronJobs(jobs: Array<Record<string, unknown>>): number {
+  return jobs.filter((job) => {
+    // Missing `enabled` counts as enabled, matching `isJobEnabled`
+    // (`src/cron/service/jobs.ts`); only an explicit `false` is excluded.
+    if (job.enabled === false) {
+      return false;
+    }
+    const state = job.state;
+    if (typeof state !== "object" || state === null) {
+      return false;
+    }
+    const consecutiveErrors = (state as { consecutiveErrors?: unknown }).consecutiveErrors;
+    return (
+      typeof consecutiveErrors === "number" &&
+      consecutiveErrors >= CHRONIC_FAILURE_MIN_CONSECUTIVE_ERRORS
+    );
+  }).length;
+}
+
 type LegacyCronRepairState = {
   storePath: string;
   quarantinePath: string;
@@ -575,6 +607,18 @@ export async function maybeRepairLegacyCronStore(params: {
     );
   }
 
+  const chronicFailureCount = countChronicallyFailingCronJobs(rawJobs);
+  if (chronicFailureCount > 0) {
+    note(
+      [
+        `${pluralize(chronicFailureCount, "cron job")} ${chronicFailureCount === 1 ? "has" : "have"} failed ${CHRONIC_FAILURE_MIN_CONSECUTIVE_ERRORS}+ runs in a row (\`state.consecutiveErrors\`), so the scheduler only re-fires ${chronicFailureCount === 1 ? "it" : "them"} on error backoff.`,
+        `- The count resets on the next successful run and also counts runs interrupted by a gateway restart, so a lasting streak means repeated task failures, repeatedly interrupted runs, or a mix. Failure alerts are opt-in, so this may be the only notice.`,
+        `- Review with ${formatCliCommand("openclaw cron list")} or ${formatCliCommand("openclaw cron show <id>")}.`,
+      ].join("\n"),
+      "Cron",
+    );
+  }
+
   const normalized = normalizeStoredCronJobs(rawJobs);
   const notifyCount = rawJobs.filter((job) => job.notify === true).length;
   const dreamingStaleCount = countStaleDreamingJobs(rawJobs);