diff --git a/src/mcp/server/session.py b/src/mcp/server/session.py
index b71b372..d918b98 100644
--- a/src/mcp/server/session.py
+++ b/src/mcp/server/session.py
@@ -126,19 +126,20 @@ class ServerSession(
             case types.InitializeRequest(params=params):
                 self._initialization_state = InitializationState.Initializing
                 self._client_params = params
-                await responder.respond(
-                    types.ServerResult(
-                        types.InitializeResult(
-                            protocolVersion=types.LATEST_PROTOCOL_VERSION,
-                            capabilities=self._init_options.capabilities,
-                            serverInfo=types.Implementation(
-                                name=self._init_options.server_name,
-                                version=self._init_options.server_version,
-                            ),
-                            instructions=self._init_options.instructions,
+                with responder:
+                    await responder.respond(
+                        types.ServerResult(
+                            types.InitializeResult(
+                                protocolVersion=types.LATEST_PROTOCOL_VERSION,
+                                capabilities=self._init_options.capabilities,
+                                serverInfo=types.Implementation(
+                                    name=self._init_options.server_name,
+                                    version=self._init_options.server_version,
+                                ),
+                                instructions=self._init_options.instructions,
+                            )
                         )
                     )
-                )
             case _:
                 if self._initialization_state != InitializationState.Initialized:
                     raise RuntimeError(
diff --git a/src/mcp/shared/session.py b/src/mcp/shared/session.py
index e21bcbc..3d3988c 100644
--- a/src/mcp/shared/session.py
+++ b/src/mcp/shared/session.py
@@ -40,6 +40,21 @@ RequestId = str | int
 
 
 class RequestResponder(Generic[ReceiveRequestT, SendResultT]):
+    """Handles responding to MCP requests and manages request lifecycle.
+
+    This class MUST be used as a context manager to ensure proper cleanup and
+    cancellation handling:
+
+    Example:
+        with request_responder as resp:
+            await resp.respond(result)
+
+    The context manager ensures:
+    1. Proper cancellation scope setup and cleanup
+    2. Request completion tracking
+    3. Cleanup of in-flight requests
+    """
+
     def __init__(
         self,
         request_id: RequestId,
@@ -55,19 +70,36 @@ class RequestResponder(Generic[ReceiveRequestT, SendResultT]):
         self._completed = False
         self._cancel_scope = anyio.CancelScope()
         self._on_complete = on_complete
+        self._entered = False  # Track if we're in a context manager
 
     def __enter__(self) -> "RequestResponder[ReceiveRequestT, SendResultT]":
+        """Enter the context manager, enabling request cancellation tracking."""
+        self._entered = True
+        self._cancel_scope = anyio.CancelScope()
         self._cancel_scope.__enter__()
         return self
 
     def __exit__(self, exc_type, exc_val, exc_tb) -> None:
+        """Exit the context manager, performing cleanup and notifying completion."""
         try:
             if self._completed:
                 self._on_complete(self)
         finally:
+            self._entered = False
+            if not self._cancel_scope:
+                raise RuntimeError("No active cancel scope")
             self._cancel_scope.__exit__(exc_type, exc_val, exc_tb)
 
     async def respond(self, response: SendResultT | ErrorData) -> None:
+        """Send a response for this request.
+
+        Must be called within a context manager block.
+        Raises:
+            RuntimeError: If not used within a context manager
+            AssertionError: If request was already responded to
+        """
+        if not self._entered:
+            raise RuntimeError("RequestResponder must be used as a context manager")
         assert not self._completed, "Request already responded to"
 
         if not self.cancelled:
@@ -79,6 +111,11 @@ class RequestResponder(Generic[ReceiveRequestT, SendResultT]):
 
     async def cancel(self) -> None:
         """Cancel this request and mark it as completed."""
+        if not self._entered:
+            raise RuntimeError("RequestResponder must be used as a context manager")
+        if not self._cancel_scope:
+            raise RuntimeError("No active cancel scope")
+
         self._cancel_scope.cancel()
         self._completed = True  # Mark as completed so it's removed from in_flight
         # Send an error response to indicate cancellation