diff --git a/src/fastmcp/server/http.py b/src/fastmcp/server/http.py
index 72d64a93e..a842f0248 100644
--- a/src/fastmcp/server/http.py
+++ b/src/fastmcp/server/http.py
@@ -3,7 +3,7 @@ from __future__ import annotations
 from collections.abc import AsyncGenerator, Callable, Generator
 from contextlib import asynccontextmanager, contextmanager
 from contextvars import ContextVar
-from typing import TYPE_CHECKING
+from typing import TYPE_CHECKING, Union
 
 from mcp.server.auth.middleware.bearer_auth import RequireAuthMiddleware
 from mcp.server.lowlevel.server import LifespanResultT
@@ -113,7 +113,7 @@ def create_base_app(
         A Starlette application
     """
     # Always add RequestContextMiddleware as the outermost middleware
-    middleware.append(Middleware(RequestContextMiddleware))
+    middleware.insert(0, Middleware(RequestContextMiddleware))
 
     return StarletteWithLifespan(
         routes=routes,