diff --git a/cron/scheduler_provider.py b/cron/scheduler_provider.py
index 28964e2301..c78549d785 100644
--- a/cron/scheduler_provider.py
+++ b/cron/scheduler_provider.py
@@ -299,6 +299,133 @@ def provider_supports_fire_cancel(provider: Any) -> bool:
     )
 
 
+DEFAULT_MISFIRE_GRACE_MINUTES = 10
+
+
+def _misfire_grace_minutes() -> float:
+    """Resolve the misfire catch-up grace window from config.
+
+    ``cron.misfire_grace_minutes`` (number, default
+    ``DEFAULT_MISFIRE_GRACE_MINUTES``). A non-positive value disables the
+    catch-up sweep entirely.
+    """
+    try:
+        from hermes_cli.config import cfg_get, load_config
+
+        return float(
+            cfg_get(
+                load_config(),
+                "cron",
+                "misfire_grace_minutes",
+                default=DEFAULT_MISFIRE_GRACE_MINUTES,
+            )
+        )
+    except Exception:
+        return float(DEFAULT_MISFIRE_GRACE_MINUTES)
+
+
+def fire_overdue_jobs(
+    provider: "CronScheduler",
+    *,
+    adapters: Any = None,
+    loop: Any = None,
+    now: Any = None,
+) -> int:
+    """Fire jobs whose scheduled time passed without an external fire arriving.
+
+    The misfire catch-up half of the hosted fire path. External providers
+    (Chronos) deliver scheduled fires over HTTP to this process's api_server
+    adapter; when that hop is down at fire time (gateway restart window,
+    api_server not bound, scheduler retry budget exhausted), the job's
+    ``next_run_at`` stays parked in the past and — because external providers
+    have no local tick loop — nothing ever runs it. The day is silently lost
+    even though the gateway may be healthy again minutes later.
+
+    Called from the gateway housekeeping loop. Deliberately:
+
+    - **No-op for the built-in provider.** Its tick loop already picks up
+      past-due jobs via ``get_due_jobs`` — local scheduling self-heals.
+    - **Routes through the provider's own two-phase fire path** — a
+      synchronous ``claim_fire`` (store CAS, so a late external retry
+      landing concurrently is de-duplicated) and then ``fire_claimed`` in
+      a daemon thread, mirroring the webhook admission pattern. The
+      housekeeping loop that calls this must never block for the length
+      of an agent run. Provider-specific re-arm logic (Chronos NAS
+      one-shots) runs exactly as for a normal fire.
+    - **Waits out a grace window** (``cron.misfire_grace_minutes``, default
+      10, non-positive disables) so the external scheduler's own retry
+      backoff gets first right to deliver — catch-up is the backstop, not
+      a race.
+    - **Operates on the process-global cron store only** — same profile
+      scoping as the external provider's reconcile.
+
+    Returns the number of jobs this sweep claimed and dispatched.
+    """
+    import logging
+    import threading
+    from datetime import datetime
+
+    logger = logging.getLogger("cron.scheduler_provider")
+
+    if isinstance(provider, InProcessCronScheduler):
+        return 0
+
+    grace_minutes = _misfire_grace_minutes()
+    if grace_minutes <= 0:
+        return 0
+
+    from cron.jobs import _ensure_aware, _hermes_now, is_job_runnable, load_jobs
+
+    if now is None:
+        now = _hermes_now()
+
+    fired = 0
+    for job in load_jobs():
+        if not is_job_runnable(job):
+            continue
+        next_run_at = job.get("next_run_at")
+        if not next_run_at:
+            continue
+        try:
+            due_dt = _ensure_aware(datetime.fromisoformat(next_run_at))
+        except (ValueError, TypeError):
+            continue
+        overdue_seconds = (now - due_dt).total_seconds()
+        if overdue_seconds < grace_minutes * 60:
+            continue
+        job_id = str(job.get("id") or "")
+        logger.warning(
+            "Misfire catch-up: job %s (%s) was due %s (%.0f min overdue) and "
+            "no external fire arrived — firing locally.",
+            job_id,
+            job.get("name") or "unnamed",
+            next_run_at,
+            overdue_seconds / 60,
+        )
+        try:
+            # Two-phase, webhook-style: claim synchronously (fast store
+            # CAS — losing means an external retry beat us, which is
+            # fine), then run the job off-thread so the caller's loop is
+            # never blocked for the length of an agent run.
+            claimed = provider.claim_fire(job_id)
+            if claimed is None:
+                continue
+            threading.Thread(
+                target=provider.fire_claimed,
+                args=(claimed,),
+                kwargs={"adapters": adapters, "loop": loop},
+                daemon=True,
+                name=f"cron-misfire-{job_id[:12]}",
+            ).start()
+            fired += 1
+        except Exception as exc:
+            logger.warning(
+                "Misfire catch-up failed for job %s: %s: %s",
+                job_id, type(exc).__name__, exc,
+            )
+    return fired
+
+
 def resolve_cron_scheduler() -> "CronScheduler":
     """Return the active cron scheduler provider.
 
diff --git a/gateway/run.py b/gateway/run.py
index a7b8e79e57..1439cc601a 100644
--- a/gateway/run.py
+++ b/gateway/run.py
@@ -29467,7 +29467,7 @@ def _run_planned_stop_watcher(
         stop_event.wait(poll_interval)
 
 
-def _start_gateway_housekeeping(stop_event: threading.Event, adapters=None, loop=None, interval: int = 60):
+def _start_gateway_housekeeping(stop_event: threading.Event, adapters=None, loop=None, interval: int = 60, cron_provider=None):
     """Background thread for gateway-only periodic chores (NOT cron).
 
     Split out of the historical ``_start_cron_ticker`` so the cron *trigger*
@@ -29496,6 +29496,7 @@ def _start_gateway_housekeeping(stop_event: threading.Event, adapters=None, loop
     CURATOR_EVERY = 60       # ticks — poll hourly (inner gate handles the real cadence)
     AUTO_ARCHIVE_EVERY = 60  # ticks — poll hourly (state_meta gate owns the real cadence)
     MEMORY_TRIM_EVERY = 1    # shared helper cooldown bounds actual allocator work
+    MISFIRE_SWEEP_EVERY = 5  # ticks — every 5 minutes (grace window gates real work)
 
     # Every platform media cache prunes on the same hourly cadence — one loop
     # over (name, cleanup_fn), not a copy-pasted try/except per cache.
@@ -29550,6 +29551,27 @@ def _start_gateway_housekeeping(stop_event: threading.Event, adapters=None, loop
             except Exception as e:
                 logger.debug("Paste sweep error: %s", e)
 
+        # Misfire catch-up (external cron providers only): fire jobs whose
+        # scheduled time passed with no external fire delivered — the
+        # backstop for a dead loopback fire hop (gateway restart window,
+        # api_server not bound, scheduler retries exhausted). The helper
+        # no-ops for the built-in ticker and enforces the
+        # cron.misfire_grace_minutes window; the store CAS claim de-dupes
+        # against a late external retry arriving concurrently.
+        if cron_provider is not None and tick_count % MISFIRE_SWEEP_EVERY == 0:
+            try:
+                from cron.scheduler_provider import fire_overdue_jobs
+
+                caught_up = fire_overdue_jobs(
+                    cron_provider, adapters=adapters, loop=loop
+                )
+                if caught_up:
+                    logger.info(
+                        "Misfire catch-up: fired %d overdue job(s)", caught_up
+                    )
+            except Exception as e:
+                logger.debug("Misfire catch-up sweep error: %s", e)
+
         # Curator — piggy-back on the housekeeping loop so long-running
         # gateways get weekly skill maintenance without needing restarts.
         # maybe_run_curator() is internally gated by config.interval_hours
@@ -30324,7 +30346,11 @@ async def start_gateway(config: Optional[GatewayConfig] = None, replace: bool =
     housekeeping_thread = threading.Thread(
         target=_start_gateway_housekeeping,
         args=(cron_stop,),
-        kwargs={"adapters": runner.adapters, "loop": asyncio.get_running_loop()},
+        kwargs={
+            "adapters": runner.adapters,
+            "loop": asyncio.get_running_loop(),
+            "cron_provider": cron_provider,
+        },
         daemon=True,
         name="gateway-housekeeping",
     )
diff --git a/tests/cron/test_misfire_catchup.py b/tests/cron/test_misfire_catchup.py
new file mode 100644
index 0000000000..53ceb31887
--- /dev/null
+++ b/tests/cron/test_misfire_catchup.py
@@ -0,0 +1,163 @@
+"""Tests for fire_overdue_jobs — misfire catch-up for external cron providers.
+
+External providers (Chronos) deliver scheduled fires over HTTP; when the
+loopback hop is down at fire time and the scheduler's retry budget exhausts,
+the job's next_run_at stays parked in the past and nothing ever runs it
+(external providers have no local tick loop). fire_overdue_jobs, called from
+gateway housekeeping, claims and fires those jobs after a grace window.
+"""
+
+import threading
+import time
+from datetime import timedelta
+
+import pytest
+
+from cron.jobs import _hermes_now, create_job, get_job, load_jobs, save_jobs
+from cron.scheduler_provider import (
+    CronScheduler,
+    InProcessCronScheduler,
+    fire_overdue_jobs,
+)
+
+
+@pytest.fixture()
+def tmp_cron_dir(tmp_path, monkeypatch):
+    """Redirect cron storage to a temp directory."""
+    monkeypatch.setattr("cron.jobs.CRON_DIR", tmp_path / "cron")
+    monkeypatch.setattr("cron.jobs.JOBS_FILE", tmp_path / "cron" / "jobs.json")
+    monkeypatch.setattr("cron.jobs.OUTPUT_DIR", tmp_path / "cron" / "output")
+    return tmp_path
+
+
+class RecordingProvider(CronScheduler):
+    """External-provider stand-in: real base-class claim_fire (store CAS),
+    recorded fire_claimed instead of the blocking run_one_job."""
+
+    def __init__(self):
+        self.fired = []
+        self._done = threading.Event()
+
+    @property
+    def name(self):
+        return "recording"
+
+    def start(self, stop_event, **kw):  # pragma: no cover - unused
+        return None
+
+    def fire_claimed(self, claimed_job, *, adapters=None, loop=None,
+                     cancel_event=None):
+        self.fired.append(claimed_job["id"])
+        self._done.set()
+        return True
+
+    def wait_fired(self, timeout=5.0):
+        return self._done.wait(timeout)
+
+
+def _park_in_past(job_id, minutes):
+    """Rewind a job's next_run_at into the past (simulates missed fires)."""
+    jobs = load_jobs()
+    for j in jobs:
+        if j["id"] == job_id:
+            j["next_run_at"] = (
+                _hermes_now() - timedelta(minutes=minutes)
+            ).isoformat()
+    save_jobs(jobs)
+
+
+class TestFireOverdueJobs:
+    def test_noop_for_builtin_provider(self, tmp_cron_dir):
+        """The in-process ticker self-heals past-due jobs — the sweep must
+        never double-dispatch under it."""
+        job = create_job(prompt="p", schedule="every 1h")
+        _park_in_past(job["id"], minutes=60)
+        assert fire_overdue_jobs(InProcessCronScheduler()) == 0
+
+    def test_fires_job_past_grace(self, tmp_cron_dir):
+        job = create_job(prompt="p", schedule="every 1h")
+        _park_in_past(job["id"], minutes=30)
+        provider = RecordingProvider()
+        assert fire_overdue_jobs(provider) == 1
+        assert provider.wait_fired()
+        assert provider.fired == [job["id"]]
+
+    def test_respects_grace_window(self, tmp_cron_dir):
+        """A job only a few minutes overdue is still the external
+        scheduler's to retry — the backstop must not race it."""
+        job = create_job(prompt="p", schedule="every 1h")
+        _park_in_past(job["id"], minutes=5)  # < default 10 min grace
+        provider = RecordingProvider()
+        assert fire_overdue_jobs(provider) == 0
+        assert provider.fired == []
+
+    def test_grace_zero_disables(self, tmp_cron_dir, monkeypatch):
+        monkeypatch.setattr(
+            "cron.scheduler_provider._misfire_grace_minutes", lambda: 0.0
+        )
+        job = create_job(prompt="p", schedule="every 1h")
+        _park_in_past(job["id"], minutes=600)
+        assert fire_overdue_jobs(RecordingProvider()) == 0
+
+    def test_future_job_not_fired(self, tmp_cron_dir):
+        create_job(prompt="p", schedule="every 1h")  # next_run_at in future
+        provider = RecordingProvider()
+        assert fire_overdue_jobs(provider) == 0
+
+    def test_paused_job_not_fired(self, tmp_cron_dir):
+        from cron.jobs import pause_job
+
+        job = create_job(prompt="p", schedule="every 1h")
+        _park_in_past(job["id"], minutes=30)
+        pause_job(job["id"])
+        assert fire_overdue_jobs(RecordingProvider()) == 0
+
+    def test_fresh_external_claim_wins(self, tmp_cron_dir):
+        """A concurrent external fire holds the store claim — the sweep's
+        claim_fire loses the CAS and must not dispatch (at-most-once)."""
+        from cron.jobs import claim_job_for_fire
+
+        job = create_job(prompt="p", schedule="every 1h")
+        _park_in_past(job["id"], minutes=30)
+        assert claim_job_for_fire(job["id"]) is True  # external fire claims
+
+        # The external claim also advanced next_run_at (recurring bump), so
+        # re-park it to isolate the claim-CAS as the thing that blocks us.
+        _park_in_past(job["id"], minutes=30)
+
+        provider = RecordingProvider()
+        assert fire_overdue_jobs(provider) == 0
+        assert provider.fired == []
+
+    def test_claim_advances_next_run_no_refire(self, tmp_cron_dir):
+        """After a catch-up fire, the recurring job's next_run_at moved to
+        the future — the next sweep pass must not fire it again."""
+        job = create_job(prompt="p", schedule="every 1h")
+        _park_in_past(job["id"], minutes=30)
+        provider = RecordingProvider()
+        assert fire_overdue_jobs(provider) == 1
+        assert provider.wait_fired()
+
+        stamped = get_job(job["id"])
+        assert stamped["next_run_at"] > _hermes_now().isoformat()
+
+        provider2 = RecordingProvider()
+        assert fire_overdue_jobs(provider2) == 0
+
+    def test_dispatch_is_nonblocking(self, tmp_cron_dir):
+        """fire_claimed runs off-thread — a slow job must not stall the
+        sweep (housekeeping loop) for the length of an agent run."""
+
+        class SlowProvider(RecordingProvider):
+            def fire_claimed(self, claimed_job, **kw):
+                time.sleep(3.0)
+                return super().fire_claimed(claimed_job, **kw)
+
+        job = create_job(prompt="p", schedule="every 1h")
+        _park_in_past(job["id"], minutes=30)
+        provider = SlowProvider()
+        start = time.monotonic()
+        assert fire_overdue_jobs(provider) == 1
+        assert time.monotonic() - start < 1.0  # returned before the run
+        assert provider.wait_fired(timeout=10)
+        assert provider.fired == [job["id"]]
diff --git a/website/docs/user-guide/features/cron.md b/website/docs/user-guide/features/cron.md
index 168d7e57d3..6e12e8e5e3 100644
--- a/website/docs/user-guide/features/cron.md
+++ b/website/docs/user-guide/features/cron.md
@@ -678,6 +678,18 @@ These misses are stamped on the job record as `last_fire_error` (timestamp + rea
 
 The stamp always reflects **current** auto-fire health: it is overwritten by newer misses and cleared automatically by the next successful run. If you see it, the job and its schedule are fine — the gateway side of the fire path needs attention (most commonly, restart the gateway through its supervisor so it loads the full profile environment: `hermes gateway restart`).
 
+### Misfire catch-up
+
+When an external scheduler provider is active (managed cron on hosted deployments), the gateway also runs a catch-up sweep: a job whose scheduled time passed with no fire delivered — and whose grace window has elapsed — is claimed and run locally, so an outage in the fire hand-off costs minutes instead of the whole day. The sweep is de-duplicated against late scheduler retries by the same store claim used for normal fires.
+
+```yaml
+cron:
+  misfire_grace_minutes: 10   # wait this long for the scheduler's own retries
+                              # before catching up locally; 0 disables catch-up
+```
+
+Local (built-in ticker) deployments don't need this — the ticker already picks up past-due jobs on its next tick.
+
 ## Schedule formats
 
 The agent's final response is automatically delivered to the job's `deliver:` target — the agent no longer fires messages itself, so the user-facing content simply goes in the final response. To deliver to **additional or different** targets, list multiple `deliver:` targets on the cron job (comma-separated, e.g. `deliver: "telegram,discord"`) rather than having the agent send them.