diff --git a/tests/server/test_http_middleware.py b/tests/server/test_http_middleware.py
new file mode 100644
index 000000000..2ff4127be
--- /dev/null
+++ b/tests/server/test_http_middleware.py
@@ -0,0 +1,219 @@
+"""Tests for custom middleware in HTTP servers."""
+
+from collections.abc import Callable
+from typing import Any
+
+import httpx
+import pytest
+from httpx import ASGITransport
+from starlette.middleware import Middleware
+from starlette.middleware.base import BaseHTTPMiddleware
+from starlette.requests import Request
+from starlette.responses import JSONResponse
+from starlette.routing import BaseRoute, Route
+from starlette.types import ASGIApp
+
+from fastmcp.server import FastMCP
+from fastmcp.server.http import create_sse_app, create_streamable_http_app
+
+
+class HeaderMiddleware(BaseHTTPMiddleware):
+    """Simple middleware that adds a custom header to responses."""
+
+    def __init__(self, app: ASGIApp, header_name: str, header_value: str):
+        super().__init__(app)
+        self.header_name = header_name
+        self.header_value = header_value
+
+    async def dispatch(self, request: Request, call_next: Callable):
+        response = await call_next(request)
+        response.headers[self.header_name] = self.header_value
+        return response
+
+
+class RequestModifierMiddleware(BaseHTTPMiddleware):
+    """Middleware that adds a value to request state."""
+
+    def __init__(self, app: ASGIApp, key: str, value: Any):
+        super().__init__(app)
+        self.key = key
+        self.value = value
+
+    async def dispatch(self, request: Request, call_next: Callable):
+        request.state.custom_value = {self.key: self.value}
+        return await call_next(request)
+
+
+async def endpoint_handler(request: Request):
+    """Endpoint that returns request state or headers."""
+    if hasattr(request.state, "custom_value"):
+        return JSONResponse({"state": request.state.custom_value})
+    return JSONResponse({"message": "Hello, world!"})
+
+
+@pytest.mark.asyncio
+async def test_sse_app_with_custom_middleware():
+    """Test that custom middleware works with SSE app."""
+    server = FastMCP(name="TestServer")
+
+    # Create custom middleware
+    custom_middleware = [
+        Middleware(
+            HeaderMiddleware, header_name="X-Custom-Header", header_value="test-value"
+        )
+    ]
+
+    # Add a test route to server's additional routes
+    routes: list[BaseRoute] = [Route("/test", endpoint_handler)]
+    server._additional_http_routes = routes
+
+    # Create the app with custom middleware
+    app = server.sse_app(middleware=custom_middleware)
+
+    # Create a test client
+    transport = ASGITransport(app=app)
+    async with httpx.AsyncClient(
+        transport=transport, base_url="http://testserver"
+    ) as client:
+        response = await client.get("/test")
+
+        # Verify middleware was applied
+        assert response.status_code == 200
+        assert response.headers["X-Custom-Header"] == "test-value"
+
+
+@pytest.mark.asyncio
+async def test_streamable_http_app_with_custom_middleware():
+    """Test that custom middleware works with StreamableHTTP app."""
+    server = FastMCP(name="TestServer")
+
+    # Create custom middleware
+    custom_middleware = [
+        Middleware(
+            HeaderMiddleware, header_name="X-Custom-Header", header_value="test-value"
+        )
+    ]
+
+    # Add a test route to server's additional routes
+    routes: list[BaseRoute] = [Route("/test", endpoint_handler)]
+    server._additional_http_routes = routes
+
+    # Create the app with custom middleware
+    app = server.streamable_http_app(middleware=custom_middleware)
+
+    # Create a test client
+    transport = ASGITransport(app=app)
+    async with httpx.AsyncClient(
+        transport=transport, base_url="http://testserver"
+    ) as client:
+        response = await client.get("/test")
+
+        # Verify middleware was applied
+        assert response.status_code == 200
+        assert response.headers["X-Custom-Header"] == "test-value"
+
+
+@pytest.mark.asyncio
+async def test_create_sse_app_with_custom_middleware():
+    """Test that custom middleware works with create_sse_app function."""
+    server = FastMCP(name="TestServer")
+
+    # Create custom middleware
+    custom_middleware = [
+        Middleware(RequestModifierMiddleware, key="modified_by", value="middleware")
+    ]
+
+    # Add a test route
+    additional_routes: list[BaseRoute] = [Route("/test", endpoint_handler)]
+
+    # Create the app with custom middleware
+    app = create_sse_app(
+        server=server,
+        message_path="/message",
+        sse_path="/sse",
+        middleware=custom_middleware,
+        routes=additional_routes,
+    )
+
+    # Create a test client
+    transport = ASGITransport(app=app)
+    async with httpx.AsyncClient(
+        transport=transport, base_url="http://testserver"
+    ) as client:
+        response = await client.get("/test")
+
+        # Verify middleware was applied
+        assert response.status_code == 200
+        data = response.json()
+        assert "state" in data
+        assert data["state"]["modified_by"] == "middleware"
+
+
+@pytest.mark.asyncio
+async def test_create_streamable_http_app_with_custom_middleware():
+    """Test that custom middleware works with create_streamable_http_app function."""
+    server = FastMCP(name="TestServer")
+
+    # Create custom middleware
+    custom_middleware = [
+        Middleware(RequestModifierMiddleware, key="modified_by", value="middleware")
+    ]
+
+    # Add a test route
+    additional_routes: list[BaseRoute] = [Route("/test", endpoint_handler)]
+
+    # Create the app with custom middleware
+    app = create_streamable_http_app(
+        server=server,
+        streamable_http_path="/streamable",
+        middleware=custom_middleware,
+        routes=additional_routes,
+    )
+
+    # Create a test client
+    transport = ASGITransport(app=app)
+    async with httpx.AsyncClient(
+        transport=transport, base_url="http://testserver"
+    ) as client:
+        response = await client.get("/test")
+
+        # Verify middleware was applied
+        assert response.status_code == 200
+        data = response.json()
+        assert "state" in data
+        assert data["state"]["modified_by"] == "middleware"
+
+
+@pytest.mark.asyncio
+async def test_multiple_middleware_ordering():
+    """Test that multiple middleware are applied in the correct order."""
+    server = FastMCP(name="TestServer")
+
+    # Create multiple middleware
+    custom_middleware = [
+        Middleware(
+            HeaderMiddleware, header_name="X-First-Header", header_value="first"
+        ),
+        Middleware(
+            HeaderMiddleware, header_name="X-Second-Header", header_value="second"
+        ),
+    ]
+
+    # Add a test route to server's additional routes
+    routes: list[BaseRoute] = [Route("/test", endpoint_handler)]
+    server._additional_http_routes = routes
+
+    # Create the app with custom middleware
+    app = server.sse_app(middleware=custom_middleware)
+
+    # Create a test client
+    transport = ASGITransport(app=app)
+    async with httpx.AsyncClient(
+        transport=transport, base_url="http://testserver"
+    ) as client:
+        response = await client.get("/test")
+
+        # Verify both middleware were applied
+        assert response.status_code == 200
+        assert response.headers["X-First-Header"] == "first"
+        assert response.headers["X-Second-Header"] == "second"