diff --git a/litellm/proxy/proxy_server.py b/litellm/proxy/proxy_server.py
index 0cc4e51da41..e3bf5949c4a 100644
--- a/litellm/proxy/proxy_server.py
+++ b/litellm/proxy/proxy_server.py
@@ -5081,6 +5081,7 @@ class ProxyConfig:
         self._last_websearch_interception_config: dict[str, object] | None = None
         self._last_hashicorp_vault_config: dict[str, object] | None = None
         self._last_cyberark_config: dict[str, object] | None = None  # mutable-ok: change-detection cache
+        self._last_cleanup_schedule_attempt: tuple[SettingsJsonValue | None, ...] | None = None
         self._cyberark_boot_env: dict[str, str | None] | None = None  # mutable-ok: deployment env snapshot, set once
         self.worker_registry: list[WorkerRegistryEntry] = []
         self.config_sync_subscriber: ConfigSyncSubscriber | None = None
@@ -7643,7 +7644,14 @@ class ProxyConfig:
         resolved: Final = self._resolved_retention_values()
         wants_job: Final = any(value is not None for value in resolved)
         has_job: Final = scheduler is not None and scheduler.get_job("spend_log_cleanup_job") is not None
-        if previous_retention_values != resolved or wants_job != has_job:
+        attempt: Final = (
+            *resolved,
+            self.settings.get("maximum_spend_logs_cleanup_cron"),
+            self.settings.get("maximum_spend_logs_retention_interval"),
+        )
+        job_missing: Final = wants_job and not has_job and attempt != self._last_cleanup_schedule_attempt
+        if previous_retention_values != resolved or job_missing or (has_job and not wants_job):
+            self._last_cleanup_schedule_attempt = attempt
             await self._reschedule_spend_log_cleanup_job()
 
     async def _apply_ssrf_settings(self, db_values: Mapping[str, SettingsJsonValue]) -> None:
diff --git a/tests/test_litellm/proxy/proxy_server/test_proxy_config.py b/tests/test_litellm/proxy/proxy_server/test_proxy_config.py
index 70debd6a4cb..33403915635 100644
--- a/tests/test_litellm/proxy/proxy_server/test_proxy_config.py
+++ b/tests/test_litellm/proxy/proxy_server/test_proxy_config.py
@@ -3918,6 +3918,28 @@ async def test_ProxyConfig__update_general_settings_schedules_cleanup_when_db_ro
     assert fake_scheduler.add_job.call_args.kwargs["id"] == "spend_log_cleanup_job"
 
 
+@pytest.mark.asyncio
+async def test_ProxyConfig__update_general_settings_retries_a_failed_schedule_once_per_settings_value(monkeypatch):
+    """An unparseable cron leaves no job behind; reloads must not retry it every tick, only when the
+    cron or a retention value changes."""
+    fake_scheduler = MagicMock()
+    fake_scheduler.get_job.return_value = None
+    monkeypatch.setattr("litellm.proxy.proxy_server.scheduler", fake_scheduler)
+    monkeypatch.setattr("litellm.proxy.proxy_server.prisma_client", None)
+    pc = ProxyConfig()
+    bad_cron = {"maximum_daily_tag_spend_retention_period": "90d", "maximum_spend_logs_cleanup_cron": "not a cron"}
+    pc.settings.apply_db_row("general_settings", bad_cron)
+    monkeypatch.setattr("litellm.proxy.proxy_server.general_settings", pc.settings)
+    for _ in range(3):
+        await pc._update_general_settings(bad_cron)
+    assert fake_scheduler.add_job.call_count == 0
+    assert fake_scheduler.remove_job.call_count == 1
+
+    await pc._update_general_settings({**bad_cron, "maximum_spend_logs_cleanup_cron": "* * * * *"})
+    assert fake_scheduler.add_job.call_count == 1
+    assert fake_scheduler.add_job.call_args.kwargs["id"] == "spend_log_cleanup_job"
+
+
 # ---------------------------------------------------------------------------
 # ProxyConfig._update_general_settings
 # ---------------------------------------------------------------------------