From 755f3e404210c93f7d0afbeb1e5f9027cf10cb41 Mon Sep 17 00:00:00 2001
From: yucheng <yucheng@berri.ai>
Date: Thu, 24 Sep 2026 18:05:21 +0000
Subject: [PATCH] fix(proxy): retry a failed cleanup schedule only when its
 settings change

_apply_retention_settings rescheduled whenever retention was set and no job existed, so an unparseable cleanup cron was retried on every config reload. Remember the last attempted retention, cron and interval tuple and retry only when it differs

Co-Authored-By: Devin AI <158243242+devin-ai-integration[bot]@users.noreply.github.com>
---
 litellm/proxy/proxy_server.py                 | 10 ++++++++-
 .../proxy/proxy_server/test_proxy_config.py   | 22 +++++++++++++++++++
 2 files changed, 31 insertions(+), 1 deletion(-)

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
 # ---------------------------------------------------------------------------