fix(auth): scope the JWT enterprise gate to actual JWTs

litellm/proxy/auth/user_api_key_auth.py

@@ -1191,13 +1191,15 @@ async def _user_api_key_auth_builder(
             return await handle_oauth2_proxy_request(request=request)
 
         if general_settings.get("enable_jwt_auth", False) is True:
-            from litellm.proxy.proxy_server import premium_user
-
-            if premium_user is not True:
-                raise ValueError(f"JWT Auth is an enterprise only feature. {CommonProxyErrors.not_premium_user.value}")
             is_jwt = jwt_handler.is_jwt(token=api_key)
             verbose_proxy_logger.debug("is_jwt: %s", is_jwt)
             if is_jwt:
+                from litellm.proxy.proxy_server import premium_user
+
+                if premium_user is not True:
+                    raise ValueError(
+                        f"JWT Auth is an enterprise only feature. {CommonProxyErrors.not_premium_user.value}"
+                    )
                 # Try JWT-to-Virtual-Key mapping first to avoid
                 # unnecessary DB queries in auth_builder
                 do_standard_jwt_auth = True

tests/test_litellm/proxy/auth/test_user_api_key_auth.py

@@ -3992,6 +3992,80 @@ async def test_non_admin_cli_session_token_reaches_production_auth_path(monkeypa
     assert result.is_session_token is True
 
 
+@pytest.mark.asyncio
+async def test_cli_session_token_authenticates_when_jwt_auth_enabled_without_license(monkeypatch):
+    """A lite login token is an encrypted (non-JWT) session blob. With
+    enable_jwt_auth on and no enterprise license (premium_user False), the JWT
+    premium gate used to fire for every request before the token was decoded, so
+    the CLI token 401'd with 'JWT Auth is an enterprise only feature' and was
+    never decrypted. The gate must apply only to actual JWTs; a non-JWT session
+    token has to keep authenticating on its own path regardless of license."""
+    monkeypatch.delenv("EXPERIMENTAL_UI_LOGIN", raising=False)
+    cli_token = _mint_cli_session_token(monkeypatch)
+
+    jwt_handler = MagicMock()
+    jwt_handler.is_jwt = JWTHandler.is_jwt
+    jwt_handler.litellm_jwtauth = LiteLLM_JWTAuth()
+
+    mock_request = MagicMock()
+    mock_request.url.path = "/v1/messages"
+    mock_request.method = "POST"
+    mock_request.headers = {"authorization": f"Bearer {cli_token}"}
+    mock_request.query_params = {}
+
+    with (
+        patch("litellm.proxy.proxy_server.general_settings", {"enable_jwt_auth": True}),
+        patch("litellm.proxy.proxy_server.premium_user", False),
+        patch("litellm.proxy.proxy_server.jwt_handler", jwt_handler),
+        patch("litellm.proxy.proxy_server.master_key", "sk-master"),
+        patch("litellm.proxy.proxy_server.prisma_client", None),
+    ):
+        result = await user_api_key_auth(
+            request=mock_request,
+            api_key=f"Bearer {cli_token}",
+        )
+
+    assert result.user_id == "cli-admin"
+    assert result.team_id == "cli-team"
+    assert result.token is not None and result.token.startswith("cli-session-")
+
+
+@pytest.mark.asyncio
+async def test_real_jwt_still_requires_license_when_jwt_auth_enabled(monkeypatch):
+    """Guard for the reorder above: the enterprise gate must still reject an
+    actual JWT when there is no license. Moving the premium check inside the
+    is_jwt branch must not open JWT auth to non-premium deployments."""
+    monkeypatch.delenv("EXPERIMENTAL_UI_LOGIN", raising=False)
+    monkeypatch.setenv("LITELLM_SALT_KEY", "sk-salt-cli-test")
+
+    jwt_token = "eyJhbGciOiJSUzI1NiJ9.eyJzdWIiOiJ1c2VyMSJ9.sig"
+    jwt_handler = MagicMock()
+    jwt_handler.is_jwt = JWTHandler.is_jwt
+    jwt_handler.litellm_jwtauth = LiteLLM_JWTAuth()
+
+    mock_request = MagicMock()
+    mock_request.url.path = "/v1/messages"
+    mock_request.method = "POST"
+    mock_request.headers = {"authorization": f"Bearer {jwt_token}"}
+    mock_request.query_params = {}
+
+    with (
+        patch("litellm.proxy.proxy_server.general_settings", {"enable_jwt_auth": True}),
+        patch("litellm.proxy.proxy_server.premium_user", False),
+        patch("litellm.proxy.proxy_server.jwt_handler", jwt_handler),
+        patch("litellm.proxy.proxy_server.master_key", "sk-master"),
+        patch("litellm.proxy.proxy_server.prisma_client", None),
+    ):
+        with pytest.raises(Exception) as exc_info:
+            await user_api_key_auth(
+                request=mock_request,
+                api_key=f"Bearer {jwt_token}",
+            )
+
+    message = str(getattr(exc_info.value, "message", exc_info.value))
+    assert "enterprise only feature" in message
+
+
 @pytest.mark.asyncio
 async def test_auth_path_caches_team_object_under_canonical_team_id_key():
     """Regression for LIT-4000: the auth builder must cache the team object under