diff --git a/cron/jobs.py b/cron/jobs.py
index 766209148d..089299bd8c 100644
--- a/cron/jobs.py
+++ b/cron/jobs.py
@@ -1854,6 +1854,7 @@ def create_job(
         "last_status": None,
         "last_error": None,
         "last_delivery_error": None,
+        "failure_streak": 0,
         # Delivery configuration
         "deliver": deliver,
         "origin": origin,  # Tracks where job was created for "origin" delivery
@@ -2282,6 +2283,15 @@ def _mark_job_run_locked(
                 if success:
                     job.pop("preflight_alerted", None)
                     job.pop("drift_alerted", None)
+                # Consecutive agent-failure streak. Any successful run resets
+                # it; delivery failures alone do NOT count (the agent did its
+                # job). Read by the scheduler's failure-delivery path to nudge
+                # the user to review a repeatedly-failing automation
+                # (Poke-inspired; see cron/scheduler._failure_streak_nudge).
+                if success:
+                    job["failure_streak"] = 0
+                else:
+                    job["failure_streak"] = int(job.get("failure_streak") or 0) + 1
                 # Track delivery failures separately — cleared on successful delivery
                 job["last_delivery_error"] = delivery_error
                 # Clear any external-fire claim so a re-armed recurring job can
diff --git a/cron/scheduler.py b/cron/scheduler.py
index 1f77030000..9eb8f28da8 100644
--- a/cron/scheduler.py
+++ b/cron/scheduler.py
@@ -148,6 +148,48 @@ def _fallback_chain_phrase() -> str:
     )
 
 
+def _failure_streak_nudge(job: dict) -> str:
+    """Return a review nudge when a recurring job keeps failing, else "".
+
+    Inspired by Poke (poke.com), which "encourages users to review recurring
+    automations that haven't been acted upon": once a recurring job has failed
+    several runs in a row, the per-run failure ping stops being information and
+    starts being noise — the useful message is "this automation needs your
+    attention (fix, pause, or remove it)".
+
+    The streak counter (``failure_streak``) is persisted by
+    ``cron.jobs.mark_job_run`` and reset on any successful run. Because the
+    failure message is delivered BEFORE ``mark_job_run`` records this run, the
+    prospective streak for the current failure is stored+1.
+
+    Threshold config: ``cron.failure_nudge_threshold`` (default 3, ``0``
+    disables the nudge). One-shot jobs never nudge — they don't recur.
+    """
+    schedule_kind = (job.get("schedule") or {}).get("kind")
+    if schedule_kind not in {"cron", "interval"}:
+        return ""
+    try:
+        cfg = load_config() or {}
+        threshold = int(
+            ((cfg.get("cron") or {}) if isinstance(cfg, dict) else {}).get(
+                "failure_nudge_threshold", 3
+            )
+        )
+    except Exception:
+        threshold = 3
+    if threshold <= 0:
+        return ""
+    streak = int(job.get("failure_streak") or 0) + 1  # +1 = this run
+    if streak < threshold:
+        return ""
+    job_ref = job.get("name") or job.get("id") or "this job"
+    return (
+        f"\nThis job has failed {streak} runs in a row — worth a review. "
+        f"Fix its prompt/config, or pause it with `hermes cron pause {job_ref}` "
+        "(resume/remove also available) to stop the noise."
+    )
+
+
 def _summarize_cron_failure_for_delivery(job: dict, error: str | None) -> str:
     """Return a compact one-line failure message for chat delivery.
 
@@ -6070,7 +6112,10 @@ def _run_one_job_body(
                     "the configuration is fixed."
                 )
             else:
-                deliver_content = final_response if success else _summarize_cron_failure_for_delivery(job, error)
+                deliver_content = final_response if success else (
+                    _summarize_cron_failure_for_delivery(job, error)
+                    + _failure_streak_nudge(job)
+                )
                 if drift_skip and not success:
                     # Drift-skip alert: bypass the generic summarizer's
                     # 180-char truncation (it would eat the remediation
diff --git a/hermes_cli/cron.py b/hermes_cli/cron.py
index 4120ab62c3..240b212b9e 100644
--- a/hermes_cli/cron.py
+++ b/hermes_cli/cron.py
@@ -182,6 +182,9 @@ def cron_list(show_all: bool = False):
                 status_display = color("ok", Colors.GREEN)
             else:
                 status_display = color(f"{last_status}: {job.get('last_error', '?')}", Colors.RED)
+                streak = int(job.get("failure_streak") or 0)
+                if streak >= 2:
+                    status_display += color(f"  ({streak} failures in a row)", Colors.RED)
             print(f"    Last run:  {last_run}  {status_display}")
 
         latest_execution = job.get("latest_execution")
diff --git a/tests/cron/test_jobs.py b/tests/cron/test_jobs.py
index 0416bdcc7c..8f195ae9ef 100644
--- a/tests/cron/test_jobs.py
+++ b/tests/cron/test_jobs.py
@@ -484,6 +484,34 @@ class TestMarkJobRun:
         assert updated["last_error"] is None
         assert updated["last_delivery_error"] == "platform 'telegram' not configured"
 
+    def test_failure_streak_increments_and_resets(self, tmp_cron_dir):
+        """failure_streak counts consecutive agent failures; success resets."""
+        job = create_job(prompt="Flaky", schedule="every 1h")
+        assert get_job(job["id"])["failure_streak"] == 0
+        mark_job_run(job["id"], success=False, error="timeout")
+        mark_job_run(job["id"], success=False, error="timeout")
+        assert get_job(job["id"])["failure_streak"] == 2
+        mark_job_run(job["id"], success=True)
+        assert get_job(job["id"])["failure_streak"] == 0
+
+    def test_failure_streak_ignores_delivery_errors(self, tmp_cron_dir):
+        """A successful run with a delivery error must not count as a failure."""
+        job = create_job(prompt="Report", schedule="every 1h")
+        mark_job_run(job["id"], success=False, error="timeout")
+        mark_job_run(job["id"], success=True, delivery_error="send failed: 502")
+        assert get_job(job["id"])["failure_streak"] == 0
+
+    def test_failure_streak_backcompat_missing_field(self, tmp_cron_dir):
+        """Jobs persisted before the field existed increment from 0."""
+        job = create_job(prompt="Old", schedule="every 1h")
+        # Simulate a pre-field record on disk.
+        jobs = load_jobs()
+        for j in jobs:
+            j.pop("failure_streak", None)
+        save_jobs(jobs)
+        mark_job_run(job["id"], success=False, error="boom")
+        assert get_job(job["id"])["failure_streak"] == 1
+
 
     def test_recurring_cron_not_disabled_when_croniter_missing(self, tmp_cron_dir, monkeypatch):
         """Regression test for issue #16265.
diff --git a/tests/cron/test_scheduler.py b/tests/cron/test_scheduler.py
index 1450b99a03..a1b8cd64e5 100644
--- a/tests/cron/test_scheduler.py
+++ b/tests/cron/test_scheduler.py
@@ -2556,3 +2556,55 @@ class TestSetCronSessionTitle:
         assert out == "Nightly Synthesis #2"
         db.get_next_title_in_lineage.assert_called_once_with("Nightly Synthesis")
 
+
+
+
+class TestFailureStreakNudge:
+    """Poke-inspired repeated-failure review nudge (_failure_streak_nudge)."""
+
+    def _job(self, streak, kind="cron", name="scout"):
+        return {
+            "id": "j1",
+            "name": name,
+            "failure_streak": streak,
+            "schedule": {"kind": kind},
+        }
+
+    def test_nudges_at_threshold(self):
+        from cron.scheduler import _failure_streak_nudge
+        # stored streak 2 + this run = 3 >= default threshold 3
+        with patch("cron.scheduler.load_config", return_value={}):
+            out = _failure_streak_nudge(self._job(2))
+        assert "failed 3 runs in a row" in out
+        assert "hermes cron pause scout" in out
+
+    def test_silent_below_threshold(self):
+        from cron.scheduler import _failure_streak_nudge
+        with patch("cron.scheduler.load_config", return_value={}):
+            assert _failure_streak_nudge(self._job(0)) == ""
+            assert _failure_streak_nudge(self._job(1)) == ""
+
+    def test_oneshot_never_nudges(self):
+        from cron.scheduler import _failure_streak_nudge
+        with patch("cron.scheduler.load_config", return_value={}):
+            assert _failure_streak_nudge(self._job(10, kind="once")) == ""
+
+    def test_config_threshold_and_disable(self):
+        from cron.scheduler import _failure_streak_nudge
+        cfg5 = {"cron": {"failure_nudge_threshold": 5}}
+        with patch("cron.scheduler.load_config", return_value=cfg5):
+            assert _failure_streak_nudge(self._job(3)) == ""
+            assert "failed 5 runs" in _failure_streak_nudge(self._job(4))
+        with patch("cron.scheduler.load_config", return_value={"cron": {"failure_nudge_threshold": 0}}):
+            assert _failure_streak_nudge(self._job(50)) == ""
+
+    def test_missing_streak_field_backcompat(self):
+        from cron.scheduler import _failure_streak_nudge
+        job = {"id": "old", "schedule": {"kind": "interval"}}  # pre-field job
+        with patch("cron.scheduler.load_config", return_value={}):
+            assert _failure_streak_nudge(job) == ""
+
+    def test_config_load_failure_falls_back(self):
+        from cron.scheduler import _failure_streak_nudge
+        with patch("cron.scheduler.load_config", side_effect=RuntimeError("boom")):
+            assert "failed 3 runs" in _failure_streak_nudge(self._job(2))
diff --git a/website/docs/user-guide/features/cron.md b/website/docs/user-guide/features/cron.md
index 38473ff7ea..7b3c7e1a6f 100644
--- a/website/docs/user-guide/features/cron.md
+++ b/website/docs/user-guide/features/cron.md
@@ -328,6 +328,21 @@ Inspect recent attempts with `hermes cron runs [job-id] --limit 20` (alias:
 `history`). Terminal history is bounded; active attempts are never pruned. The
 ledger is included in quick backups.
 
+### Repeated-failure review nudge
+
+Each job tracks a `failure_streak` — consecutive runs where the agent failed
+(delivery failures don't count). When a *recurring* job's streak reaches the
+threshold, the failure message delivered to chat gains a review nudge telling
+you the job has failed N runs in a row and suggesting you fix, pause
+(`hermes cron pause <job>`), or remove it. Any successful run resets the
+streak, and `hermes cron list` shows the streak alongside a failing job's last
+run. One-shot jobs never nudge.
+
+```yaml
+cron:
+  failure_nudge_threshold: 3   # default; 0 disables the nudge
+```
+
 ## Delivery options
 
 When scheduling jobs, you specify where the output goes: