diff --git a/cron/jobs.py b/cron/jobs.py
index 851e15b5eeb..62633ff2d73 100644
--- a/cron/jobs.py
+++ b/cron/jobs.py
@@ -1186,7 +1186,14 @@ def update_job(job_id: str, updates: Dict[str, Any]) -> Optional[Dict[str, Any]]
                 updated["model_snapshot"] = model_snapshot
 
             if updated.get("enabled", True) and updated.get("state") != "paused" and not updated.get("next_run_at"):
-                updated["next_run_at"] = compute_next_run(updated["schedule"])
+                next_run = compute_next_run(updated["schedule"])
+                if next_run is None and updated["schedule"].get("kind") == "once":
+                    run_at = updated["schedule"].get("run_at", "unknown")
+                    raise ValueError(
+                        f"Requested one-shot time {run_at} is in the past "
+                        f"(grace window: {ONESHOT_GRACE_SECONDS}s) and cannot be scheduled."
+                    )
+                updated["next_run_at"] = next_run
 
             jobs[i] = updated
             save_jobs(jobs)
@@ -1217,6 +1224,12 @@ def resume_job(job_id: str) -> Optional[Dict[str, Any]]:
         return None
 
     next_run_at = compute_next_run(job["schedule"])
+    if next_run_at is None and job["schedule"].get("kind") == "once":
+        run_at = job["schedule"].get("run_at", "unknown")
+        raise ValueError(
+            f"Cannot resume: one-shot time {run_at} is in the past "
+            f"(grace window: {ONESHOT_GRACE_SECONDS}s) and will never fire."
+        )
     return update_job(
         job["id"],
         {
diff --git a/tests/cron/test_jobs.py b/tests/cron/test_jobs.py
index 4ba0e966dc5..67f3e772f18 100644
--- a/tests/cron/test_jobs.py
+++ b/tests/cron/test_jobs.py
@@ -444,6 +444,35 @@ class TestPauseResumeJob:
         assert resumed["paused_at"] is None
         assert resumed["paused_reason"] is None
 
+    def test_resume_rejects_past_oneshot(self, tmp_cron_dir, monkeypatch):
+        """Resuming a paused one-shot whose time is now in the past must raise
+        ValueError — the revived job would silently never fire."""
+        now = datetime(2026, 7, 6, 12, 0, 0, tzinfo=timezone.utc)
+        monkeypatch.setattr("cron.jobs._hermes_now", lambda: now)
+        # Create directly — bypass create_job's past-oneshot guard so we can
+        # test the resume path independently.
+        job = {
+            "id": "test-resume-past",
+            "name": "test-resume-past",
+            "prompt": "Past one-shot",
+            "schedule": {"kind": "once", "run_at": (now - timedelta(minutes=5)).isoformat(), "display": "once"},
+            "repeat": {"times": 1, "completed": 0},
+            "enabled": False,
+            "state": "paused",
+            "paused_at": now.isoformat(),
+            "paused_reason": "test",
+            "next_run_at": None,
+            "last_run_at": None,
+            "last_status": None,
+            "last_error": None,
+            "last_delivery_error": None,
+            "created_at": (now - timedelta(hours=1)).isoformat(),
+            "deliver": "local",
+        }
+        save_jobs([job])
+        with pytest.raises(ValueError, match="in the past"):
+            resume_job("test-resume-past")
+
 
 class TestResolveJobRef:
     """Name-based job lookup for CLI/tool callers (PR #2627, @buntingszn)."""