diff --git a/litellm/proxy/auth/user_api_key_auth.py b/litellm/proxy/auth/user_api_key_auth.py
index c44723a4bb9..caa886c0a7c 100644
--- a/litellm/proxy/auth/user_api_key_auth.py
+++ b/litellm/proxy/auth/user_api_key_auth.py
@@ -2737,12 +2737,17 @@ async def user_api_key_auth_builder(
         if (
             prisma_client is None
         ):  # if both master key + user key submitted, and user key != master key, and no db connected, raise an error
-            if not PrismaDBExceptionHandler.is_database_configured():
+            if (
+                not PrismaDBExceptionHandler.is_database_configured()
+                and PrismaDBExceptionHandler.should_allow_request_on_db_unavailable()
+            ):
                 # No database was ever configured, so there is no outage to
                 # ride out. ``allow_requests_on_db_unavailable`` must not fail
                 # open here: a non-master key cannot be verified and is
                 # rejected, instead of being admitted via the
-                # ``no_db_connection`` fallback token. See #47119.
+                # ``no_db_connection`` fallback token. See #47119. When the
+                # flag is off no fallback token is issued anyway, so the
+                # established ``no_db_connection`` error below stands.
                 raise ProxyException(
                     message="Authentication Error - No database configured. Virtual keys require a configured database; only the master key can be used without one.",
                     type=ProxyErrorTypes.auth_error,
diff --git a/litellm/proxy/db/exception_handler.py b/litellm/proxy/db/exception_handler.py
index 0458af22b7e..3f5d4558716 100644
--- a/litellm/proxy/db/exception_handler.py
+++ b/litellm/proxy/db/exception_handler.py
@@ -1,5 +1,6 @@
 import os
 import re
+import sys
 from collections.abc import Awaitable, Callable, Iterator
 from http import HTTPStatus
 from typing import Final, Protocol, TypeVar
@@ -107,14 +108,13 @@ class PrismaDBExceptionHandler:
         """
         if os.getenv("DATABASE_URL") or os.getenv("DIRECT_URL"):
             return True
-        try:
-            from litellm.proxy.proxy_server import general_settings
-
-            if isinstance(general_settings, dict):
-                return bool(general_settings.get("database_url"))
-        except Exception:
-            return False
-        return False
+        # Read ``general_settings`` through ``sys.modules``: importing
+        # ``proxy_server`` here could fail or recurse while it is still
+        # being imported, and a proxy server that has not been imported
+        # yet has not configured a database through it either.
+        proxy_server_module = sys.modules.get("litellm.proxy.proxy_server")
+        general_settings = getattr(proxy_server_module, "general_settings", None)
+        return isinstance(general_settings, dict) and bool(general_settings.get("database_url"))
 
     @staticmethod
     def is_database_connection_error(e: Exception) -> bool:
diff --git a/tests/unit/proxy/db/test_exception_handler.py b/tests/unit/proxy/db/test_exception_handler.py
index f21f2e82748..a0391781cd5 100644
--- a/tests/unit/proxy/db/test_exception_handler.py
+++ b/tests/unit/proxy/db/test_exception_handler.py
@@ -964,3 +964,9 @@ def test_is_database_configured(monkeypatch):
     monkeypatch.setenv("DATABASE_URL", "postgresql://user:pass@localhost:5432/litellm")
     with patch("litellm.proxy.proxy_server.general_settings", {}):
         assert PrismaDBExceptionHandler.is_database_configured() is True
+    monkeypatch.delenv("DATABASE_URL", raising=False)
+    with patch(
+        "litellm.proxy.proxy_server.general_settings",
+        {"database_url": "postgresql://localhost:5432/litellm"},
+    ):
+        assert PrismaDBExceptionHandler.is_database_configured() is True