diff --git a/litellm/proxy/proxy_server.py b/litellm/proxy/proxy_server.py
index e3bf5949c4a..af51a05f782 100644
--- a/litellm/proxy/proxy_server.py
+++ b/litellm/proxy/proxy_server.py
@@ -7649,10 +7649,14 @@ class ProxyConfig:
             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):
+        last_attempt: Final = self._last_cleanup_schedule_attempt
+        schedule_changed: Final = last_attempt is not None and attempt != last_attempt
+        job_missing: Final = wants_job and not has_job and attempt != last_attempt
+        if previous_retention_values != resolved or schedule_changed or job_missing or (has_job and not wants_job):
             self._last_cleanup_schedule_attempt = attempt
             await self._reschedule_spend_log_cleanup_job()
+        elif last_attempt is None:
+            self._last_cleanup_schedule_attempt = attempt
 
     async def _apply_ssrf_settings(self, db_values: Mapping[str, SettingsJsonValue]) -> None:
         _apply_ssrf_general_settings(db_values)
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 33403915635..ab7803d28a6 100644
--- a/tests/test_litellm/proxy/proxy_server/test_proxy_config.py
+++ b/tests/test_litellm/proxy/proxy_server/test_proxy_config.py
@@ -3940,6 +3940,28 @@ async def test_ProxyConfig__update_general_settings_retries_a_failed_schedule_on
     assert fake_scheduler.add_job.call_args.kwargs["id"] == "spend_log_cleanup_job"
 
 
+@pytest.mark.asyncio
+async def test_ProxyConfig__update_general_settings_reschedules_when_only_the_cron_changes(monkeypatch):
+    fake_scheduler = MagicMock()
+    fake_scheduler.get_job.return_value = MagicMock()
+    monkeypatch.setattr("litellm.proxy.proxy_server.scheduler", fake_scheduler)
+    monkeypatch.setattr("litellm.proxy.proxy_server.prisma_client", None)
+    pc = ProxyConfig()
+    hourly = {"maximum_daily_tag_spend_retention_period": "90d", "maximum_spend_logs_cleanup_cron": "0 * * * *"}
+    pc.settings.apply_db_row("general_settings", hourly)
+    monkeypatch.setattr("litellm.proxy.proxy_server.general_settings", pc.settings)
+    await pc._update_general_settings(hourly)
+    await pc._update_general_settings(hourly)
+    assert fake_scheduler.add_job.call_count == 0
+
+    daily = {**hourly, "maximum_spend_logs_cleanup_cron": "0 3 * * *"}
+    pc.settings.apply_db_row("general_settings", daily)
+    await pc._update_general_settings(daily)
+    assert fake_scheduler.add_job.call_count == 1
+    assert fake_scheduler.add_job.call_args.kwargs["id"] == "spend_log_cleanup_job"
+    assert "hour='3'" in str(fake_scheduler.add_job.call_args.args[1])
+
+
 # ---------------------------------------------------------------------------
 # ProxyConfig._update_general_settings
 # ---------------------------------------------------------------------------