diff --git a/litellm/proxy/proxy_server.py b/litellm/proxy/proxy_server.py
index 7cb2954c10e..92d98606b23 100644
--- a/litellm/proxy/proxy_server.py
+++ b/litellm/proxy/proxy_server.py
@@ -7630,7 +7630,10 @@ class ProxyConfig:
         db_values: Mapping[str, SettingsJsonValue],
         previous_retention_values: tuple[SettingsJsonValue | None, ...],
     ) -> None:
-        if previous_retention_values != self._resolved_retention_values():
+        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:
             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 10e02634023..6d7b89dfd09 100644
--- a/tests/test_litellm/proxy/proxy_server/test_proxy_config.py
+++ b/tests/test_litellm/proxy/proxy_server/test_proxy_config.py
@@ -3808,6 +3808,7 @@ async def test_ProxyConfig__reschedule_spend_log_cleanup_job_daily_tag_spend_ret
 async def test_ProxyConfig__update_general_settings_updates_daily_tag_spend_retention(monkeypatch):
     settings = {}
     monkeypatch.setattr("litellm.proxy.proxy_server.general_settings", settings)
+    monkeypatch.setattr("litellm.proxy.proxy_server.scheduler", None)
     pc = ProxyConfig()
     reschedule = AsyncMock()
     monkeypatch.setattr(pc, "_reschedule_spend_log_cleanup_job", reschedule)
@@ -3818,6 +3819,22 @@ async def test_ProxyConfig__update_general_settings_updates_daily_tag_spend_rete
     reschedule.assert_awaited_once()
 
 
+@pytest.mark.asyncio
+async def test_ProxyConfig__update_general_settings_schedules_cleanup_when_db_row_was_already_applied(monkeypatch):
+    """A config reload applies the db row to the store before the side effects run, so the
+    before/after snapshot is equal; the job must still be scheduled when none is running."""
+    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()
+    pc.settings.apply_db_row("general_settings", {"maximum_daily_tag_spend_retention_period": "90d"})
+    monkeypatch.setattr("litellm.proxy.proxy_server.general_settings", pc.settings)
+    await pc._update_general_settings({"maximum_daily_tag_spend_retention_period": "90d"})
+    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
 # ---------------------------------------------------------------------------
@@ -3949,6 +3966,7 @@ async def test_ProxyConfig__update_general_settings_skips_redundant_retention_re
     pc = ProxyConfig()
     reschedule: Final = AsyncMock()
     monkeypatch.setattr(proxy_server, "general_settings", {})
+    monkeypatch.setattr(proxy_server, "scheduler", MagicMock())
     monkeypatch.setattr(pc, "_reschedule_spend_log_cleanup_job", reschedule)
 
     await pc._update_general_settings({"maximum_health_check_retention_period": "30d"})