diff --git a/src/gitea_codex_bot/config.py b/src/gitea_codex_bot/config.py
index c010ac9..0bd792e 100644
--- a/src/gitea_codex_bot/config.py
+++ b/src/gitea_codex_bot/config.py
@@ -65,6 +65,8 @@ class Settings(BaseSettings):
 
     @model_validator(mode="after")
     def validate_job_lease_timeout(self) -> "Settings":
+        if self.max_stuck_job_retries < 0:
+            raise ValueError("MAX_STUCK_JOB_RETRIES must be >= 0.")
         minimum_lease_timeout = (self.max_review_minutes * 60) + 60
         if self.job_lease_timeout_seconds < minimum_lease_timeout:
             raise ValueError(
diff --git a/src/gitea_codex_bot/services/jobs.py b/src/gitea_codex_bot/services/jobs.py
index 03ca2ef..6964d72 100644
--- a/src/gitea_codex_bot/services/jobs.py
+++ b/src/gitea_codex_bot/services/jobs.py
@@ -172,6 +172,15 @@ def recover_stuck_jobs(session: Session, *, lease_timeout_seconds: int, action:
             latest_run.status = RunStatus.failed
             latest_run.finished_at = now
             latest_run.error_message = message
+        else:
+            session.add(
+                ReviewRun(
+                    job_id=job.id,
+                    status=RunStatus.failed,
+                    finished_at=now,
+                    error_message=message,
+                )
+            )
         job.last_error = message
         if should_fail:
             job.status = JobStatus.failed
diff --git a/tests/test_config.py b/tests/test_config.py
index 3b3a903..b879836 100644
--- a/tests/test_config.py
+++ b/tests/test_config.py
@@ -23,3 +23,11 @@ def test_job_lease_timeout_must_cover_max_review_runtime(monkeypatch: pytest.Mon
 
     with pytest.raises(ValidationError, match="JOB_LEASE_TIMEOUT_SECONDS must be at least"):
         get_settings()
+
+
+def test_max_stuck_job_retries_must_be_non_negative(monkeypatch: pytest.MonkeyPatch) -> None:
+    monkeypatch.setenv("MAX_STUCK_JOB_RETRIES", "-1")
+    get_settings.cache_clear()
+
+    with pytest.raises(ValidationError, match="MAX_STUCK_JOB_RETRIES must be >= 0"):
+        get_settings()
diff --git a/tests/test_transitions.py b/tests/test_transitions.py
index 8166f14..03277fb 100644
--- a/tests/test_transitions.py
+++ b/tests/test_transitions.py
@@ -169,3 +169,49 @@ def test_requeue_allows_one_retry_then_fails_on_second_timeout() -> None:
         assert second[0].failed is True
         failed = session.execute(select(ReviewJob).where(ReviewJob.id == job.id)).scalar_one()
         assert failed.status == JobStatus.failed
+
+
+def test_recovery_persists_timeout_retry_even_if_latest_run_not_running() -> None:
+    session_factory = get_session_factory()
+    with session_factory() as session:
+        job = enqueue_job(
+            session,
+            repo="acme/repo",
+            pr_number=5,
+            head_sha="33334444",
+            trigger_comment_id=1005,
+            trigger_comment_body="@codex review",
+            requested_by="alice",
+            command=ParsedCommand(name="review", raw="@codex review"),
+        )
+        claimed = claim_next_job(session)
+        assert claimed is not None
+        assert claimed.id == job.id
+
+    with session_factory() as session:
+        latest_run = session.execute(select(ReviewRun).where(ReviewRun.job_id == job.id).order_by(ReviewRun.id.desc()).limit(1)).scalar_one()
+        latest_run.status = RunStatus.succeeded
+        latest_run.finished_at = datetime.now(timezone.utc)
+        stale = session.execute(select(ReviewJob).where(ReviewJob.id == job.id)).scalar_one()
+        stale.started_at = datetime.now(timezone.utc) - timedelta(seconds=601)
+        session.commit()
+
+    with session_factory() as session:
+        first = recover_stuck_jobs(session, lease_timeout_seconds=300, action="requeue", max_retries=1)
+        assert len(first) == 1
+        assert first[0].failed is False
+        claimed_again = claim_next_job(session)
+        assert claimed_again is not None
+        assert claimed_again.id == job.id
+
+    with session_factory() as session:
+        stale_again = session.execute(select(ReviewJob).where(ReviewJob.id == job.id)).scalar_one()
+        stale_again.started_at = datetime.now(timezone.utc) - timedelta(seconds=601)
+        session.commit()
+
+    with session_factory() as session:
+        second = recover_stuck_jobs(session, lease_timeout_seconds=300, action="requeue", max_retries=1)
+        assert len(second) == 1
+        assert second[0].failed is True
+        final = session.execute(select(ReviewJob).where(ReviewJob.id == job.id)).scalar_one()
+        assert final.status == JobStatus.failed