diff --git a/hermes_cli/backup.py b/hermes_cli/backup.py
index 206808267..0c6bf8692 100644
--- a/hermes_cli/backup.py
+++ b/hermes_cli/backup.py
@@ -670,6 +670,105 @@ def restore_quick_snapshot(
     return restored > 0
 
 
+# Relative path of the cron job database inside HERMES_HOME. Kept in sync with
+# the entry in ``_QUICK_STATE_FILES`` and with ``cron/jobs.py``'s ``JOBS_FILE``.
+_CRON_JOBS_REL = "cron/jobs.json"
+
+
+def _count_cron_jobs(path: Path) -> Optional[int]:
+    """Return the number of cron jobs stored in ``path``.
+
+    The canonical on-disk shape is ``{"jobs": [...]}`` (see ``cron/jobs.py``).
+    A legacy bare-list shape (``[...]``) is also honoured.
+
+    Returns:
+        The job count for any *valid, readable* JSON document, or ``None`` if
+        the file is missing or cannot be parsed. ``None`` means "unknown" —
+        callers must not treat it as "zero jobs", because acting on an
+        unreadable file could mask a real corruption the user needs to see.
+    """
+    if not path.is_file():
+        return None
+    try:
+        with open(path, "r", encoding="utf-8") as f:
+            data = json.load(f)
+    except (OSError, json.JSONDecodeError):
+        return None
+    if isinstance(data, dict):
+        jobs = data.get("jobs", [])
+        return len(jobs) if isinstance(jobs, list) else None
+    if isinstance(data, list):
+        return len(data)
+    return None
+
+
+def restore_cron_jobs_if_emptied(
+    snapshot_id: str,
+    hermes_home: Optional[Path] = None,
+) -> Optional[Dict[str, Any]]:
+    """Safety net for silent cron-job loss across ``hermes update``.
+
+    Config-version migrations have been observed to leave ``cron/jobs.json``
+    valid-but-empty after an update, silently dropping every scheduled job
+    (issue #34600). The existing malformed-shape guards in ``cron/jobs.py``
+    don't catch this case because ``{"jobs": []}`` is perfectly valid JSON.
+
+    This compares the *current* job count against the pre-update snapshot. If
+    the live file now has **zero** jobs while the snapshot captured **one or
+    more**, the snapshot copy of ``cron/jobs.json`` is restored in place.
+
+    The check is deliberately conservative — it only ever restores when there
+    is unambiguous evidence of loss (snapshot had jobs, live file has none),
+    so a user who genuinely deleted all their jobs during/after the update is
+    never second-guessed, and an unreadable live file (count ``None``) is left
+    untouched so real corruption still surfaces.
+
+    Args:
+        snapshot_id: The pre-update quick-snapshot id (from
+            :func:`create_quick_snapshot`).
+        hermes_home: Override for the Hermes home directory (tests).
+
+    Returns:
+        ``None`` when no action was taken (the common, healthy path). On a
+        successful restore, a dict ``{"restored": True, "job_count": N,
+        "snapshot_id": ...}`` so the caller can warn the user.
+    """
+    if not snapshot_id:
+        return None
+
+    home = hermes_home or get_hermes_home()
+    live_path = home / _CRON_JOBS_REL
+
+    live_count = _count_cron_jobs(live_path)
+    # Only act when the live file is readable AND empty. ``None`` (missing or
+    # unparseable) is intentionally left alone — that's a different failure
+    # mode the user should see rather than have papered over.
+    if live_count is None or live_count > 0:
+        return None
+
+    snap_path = _quick_snapshot_root(home) / snapshot_id / _CRON_JOBS_REL
+    snap_count = _count_cron_jobs(snap_path)
+    if not snap_count:  # None or 0 — nothing worth restoring
+        return None
+
+    try:
+        live_path.parent.mkdir(parents=True, exist_ok=True)
+        shutil.copy2(snap_path, live_path)
+    except (OSError, PermissionError) as exc:
+        logger.error(
+            "Cron jobs were emptied during update but auto-restore failed: %s", exc
+        )
+        return None
+
+    logger.warning(
+        "Restored %d cron job(s) from pre-update snapshot %s "
+        "(cron/jobs.json was emptied during migration)",
+        snap_count,
+        snapshot_id,
+    )
+    return {"restored": True, "job_count": snap_count, "snapshot_id": snapshot_id}
+
+
 def _prune_quick_snapshots(root: Path, keep: int = _QUICK_DEFAULT_KEEP) -> int:
     """Remove oldest quick snapshots beyond the keep limit. Returns count deleted."""
     if not root.exists():
diff --git a/hermes_cli/main.py b/hermes_cli/main.py
index 8540048aa..76bd12a53 100644
--- a/hermes_cli/main.py
+++ b/hermes_cli/main.py
@@ -9125,12 +9125,13 @@ def _cmd_update_impl(args, gateway_mode: bool):
         # though `git pull` can't touch $HERMES_HOME, this is cheap
         # belt-and-suspenders insurance and gives the user something to
         # restore from via `/snapshot list` / `/snapshot restore <id>`.
+        pre_update_snapshot_id = None
         try:
             from hermes_cli.backup import create_quick_snapshot
 
-            snap_id = create_quick_snapshot(label="pre-update", keep=1)
-            if snap_id:
-                print(f"  ✓ Pre-update snapshot: {snap_id}")
+            pre_update_snapshot_id = create_quick_snapshot(label="pre-update", keep=1)
+            if pre_update_snapshot_id:
+                print(f"  ✓ Pre-update snapshot: {pre_update_snapshot_id}")
         except Exception as exc:
             # Never let a snapshot failure block an update.
             logger.debug("Pre-update snapshot failed: %s", exc)
@@ -9467,6 +9468,25 @@ def _cmd_update_impl(args, gateway_mode: bool):
         else:
             print("  ✓ Configuration is up to date")
 
+        # Safety net: config-version migrations have been observed to leave
+        # cron/jobs.json valid-but-empty, silently dropping every scheduled
+        # job (issue #34600). If the live file is now empty while the
+        # pre-update snapshot held jobs, restore it and warn loudly.
+        try:
+            from hermes_cli.backup import restore_cron_jobs_if_emptied
+
+            cron_restore = restore_cron_jobs_if_emptied(pre_update_snapshot_id)
+            if cron_restore:
+                print()
+                print(
+                    "  ⚠️  cron/jobs.json was emptied during this update — "
+                    f"restored {cron_restore['job_count']} job(s) from "
+                    f"pre-update snapshot {cron_restore['snapshot_id']}."
+                )
+        except Exception as exc:
+            # Never let the cron safety net break an otherwise-good update.
+            logger.debug("Cron jobs auto-restore check failed: %s", exc)
+
         print()
         print("✓ Update complete!")
 
diff --git a/tests/hermes_cli/test_backup.py b/tests/hermes_cli/test_backup.py
index a8657d770..8c0f2a398 100644
--- a/tests/hermes_cli/test_backup.py
+++ b/tests/hermes_cli/test_backup.py
@@ -1679,3 +1679,105 @@ class TestPreMigrationBackup:
             _t.sleep(1.05)
         # Update backup must still be there
         assert update_backup.exists(), "pre-migration rotation wrongly pruned the pre-update backup"
+
+
+# ---------------------------------------------------------------------------
+# Cron jobs auto-restore after silent migration loss (issue #34600)
+# ---------------------------------------------------------------------------
+
+class TestRestoreCronJobsIfEmptied:
+    """`hermes update` config migration can leave cron/jobs.json valid-but-empty,
+    silently dropping every scheduled job. `restore_cron_jobs_if_emptied` is the
+    post-migration safety net that restores from the pre-update snapshot."""
+
+    @staticmethod
+    def _seed_jobs(path: Path, jobs):
+        path.parent.mkdir(parents=True, exist_ok=True)
+        path.write_text(json.dumps({"jobs": jobs}))
+
+    def _make_snapshot(self, hermes_home: Path, label="pre-update"):
+        from hermes_cli.backup import create_quick_snapshot
+        return create_quick_snapshot(label=label, hermes_home=hermes_home, keep=5)
+
+    def test_restores_when_emptied_after_migration(self, tmp_path):
+        from hermes_cli.backup import restore_cron_jobs_if_emptied
+        hermes_home = tmp_path / ".hermes"
+        jobs_path = hermes_home / "cron" / "jobs.json"
+        # Pre-update: 3 real jobs.
+        self._seed_jobs(jobs_path, [{"id": "a"}, {"id": "b"}, {"id": "c"}])
+        snap_id = self._make_snapshot(hermes_home)
+        assert snap_id
+
+        # Migration silently empties the file (valid JSON, zero jobs).
+        jobs_path.write_text(json.dumps({"jobs": []}))
+
+        result = restore_cron_jobs_if_emptied(snap_id, hermes_home=hermes_home)
+        assert result is not None
+        assert result["restored"] is True
+        assert result["job_count"] == 3
+        assert result["snapshot_id"] == snap_id
+
+        # The live file now has the jobs back.
+        restored = json.loads(jobs_path.read_text())
+        assert len(restored["jobs"]) == 3
+
+    def test_noop_when_live_file_still_has_jobs(self, tmp_path):
+        from hermes_cli.backup import restore_cron_jobs_if_emptied
+        hermes_home = tmp_path / ".hermes"
+        jobs_path = hermes_home / "cron" / "jobs.json"
+        self._seed_jobs(jobs_path, [{"id": "a"}, {"id": "b"}])
+        snap_id = self._make_snapshot(hermes_home)
+
+        # Healthy path: file unchanged after update.
+        result = restore_cron_jobs_if_emptied(snap_id, hermes_home=hermes_home)
+        assert result is None
+
+    def test_noop_when_snapshot_had_no_jobs(self, tmp_path):
+        from hermes_cli.backup import restore_cron_jobs_if_emptied
+        hermes_home = tmp_path / ".hermes"
+        jobs_path = hermes_home / "cron" / "jobs.json"
+        # Pre-update genuinely had zero jobs; current is also empty.
+        self._seed_jobs(jobs_path, [])
+        snap_id = self._make_snapshot(hermes_home)
+        jobs_path.write_text(json.dumps({"jobs": []}))
+
+        result = restore_cron_jobs_if_emptied(snap_id, hermes_home=hermes_home)
+        assert result is None
+
+    def test_noop_when_live_file_unreadable(self, tmp_path):
+        """An unparseable live file is left alone — that's a different failure
+        mode the user should see, not silently overwrite."""
+        from hermes_cli.backup import restore_cron_jobs_if_emptied
+        hermes_home = tmp_path / ".hermes"
+        jobs_path = hermes_home / "cron" / "jobs.json"
+        self._seed_jobs(jobs_path, [{"id": "a"}])
+        snap_id = self._make_snapshot(hermes_home)
+        jobs_path.write_text("{ this is not valid json")
+
+        result = restore_cron_jobs_if_emptied(snap_id, hermes_home=hermes_home)
+        assert result is None
+        # File left untouched.
+        assert jobs_path.read_text() == "{ this is not valid json"
+
+    def test_noop_when_snapshot_id_missing(self, tmp_path):
+        from hermes_cli.backup import restore_cron_jobs_if_emptied
+        hermes_home = tmp_path / ".hermes"
+        jobs_path = hermes_home / "cron" / "jobs.json"
+        self._seed_jobs(jobs_path, [])
+        assert restore_cron_jobs_if_emptied(None, hermes_home=hermes_home) is None
+        assert restore_cron_jobs_if_emptied("", hermes_home=hermes_home) is None
+
+    def test_restores_legacy_bare_list_snapshot_shape(self, tmp_path):
+        """A legacy snapshot storing a bare JSON list (not {"jobs": [...]}) is
+        still counted and restored."""
+        from hermes_cli.backup import restore_cron_jobs_if_emptied
+        hermes_home = tmp_path / ".hermes"
+        jobs_path = hermes_home / "cron" / "jobs.json"
+        jobs_path.parent.mkdir(parents=True, exist_ok=True)
+        jobs_path.write_text(json.dumps([{"id": "a"}, {"id": "b"}]))
+        snap_id = self._make_snapshot(hermes_home)
+
+        jobs_path.write_text(json.dumps({"jobs": []}))
+        result = restore_cron_jobs_if_emptied(snap_id, hermes_home=hermes_home)
+        assert result is not None
+        assert result["job_count"] == 2