diff --git a/src/mcp/client/session.py b/src/mcp/client/session.py
index 7151d57cd..d6ce1d8c5 100644
--- a/src/mcp/client/session.py
+++ b/src/mcp/client/session.py
@@ -1,4 +1,5 @@
 import logging
+from types import TracebackType
 from typing import Any, Protocol
 
 import anyio.lowlevel
@@ -107,6 +108,8 @@ class ClientSession(
         types.ServerNotification,
     ]
 ):
+    _entered: bool
+
     def __init__(
         self,
         read_stream: MemoryObjectReceiveStream[SessionMessage | Exception],
@@ -133,10 +136,29 @@ def __init__(
         self._tool_output_schemas: dict[str, dict[str, Any] | None] = {}
         self._server_capabilities: types.ServerCapabilities | None = None
         self._experimental_features: ExperimentalClientFeatures | None = None
+        self._entered = False
 
         # Experimental: Task handlers (use defaults if not provided)
         self._task_handlers = experimental_task_handlers or ExperimentalTaskHandlers()
 
+    async def __aenter__(self) -> "ClientSession":
+        self._entered = True
+        await super().__aenter__()
+        return self
+
+    async def __aexit__(
+        self,
+        exc_type: type[BaseException] | None,
+        exc_value: BaseException | None,
+        traceback: TracebackType | None,
+    ) -> None:
+        self._entered = False
+        await super().__aexit__(exc_type, exc_value, traceback)
+
+    def _check_is_active(self) -> None:
+        if not self._entered:
+            raise RuntimeError("ClientSession must be used within an 'async with' block.")
+
     @property
     def _receive_request_adapter(self) -> TypeAdapter[types.ServerRequest]:
         return types.server_request_adapter
@@ -146,6 +168,7 @@ def _receive_notification_adapter(self) -> TypeAdapter[types.ServerNotification]
         return types.server_notification_adapter
 
     async def initialize(self) -> types.InitializeResult:
+        self._check_is_active()
         sampling = (
             (self._sampling_capabilities or types.SamplingCapability())
             if self._sampling_callback is not _default_sampling_callback
diff --git a/tests/client/test_session.py b/tests/client/test_session.py
index 5c1f55d23..51b38a270 100644
--- a/tests/client/test_session.py
+++ b/tests/client/test_session.py
@@ -1,4 +1,4 @@
-from typing import Any
+from typing import Any, cast
 
 import anyio
 import pytest
@@ -705,3 +705,18 @@ async def mock_server():
         await session.initialize()
 
         await session.call_tool(name=mocked_tool.name, arguments={"foo": "bar"}, meta=meta)
+
+
+@pytest.mark.anyio
+async def test_initialize_without_context_manager_raises_error():
+    """Test that calling initialize() without entering the context manager raises RuntimeError."""
+    send_stream, receive_stream = anyio.create_memory_object_stream[Any](0)
+
+    read_stream = cast(Any, receive_stream)
+    write_stream = cast(Any, send_stream)
+
+    async with send_stream, receive_stream:
+        session = ClientSession(read_stream, write_stream)
+
+        with pytest.raises(RuntimeError, match="must be used within"):
+            await session.initialize()