diff --git a/src/mudlib/commands/play.py b/src/mudlib/commands/play.py
index df5cfbd..5fc2b03 100644
--- a/src/mudlib/commands/play.py
+++ b/src/mudlib/commands/play.py
@@ -39,9 +39,11 @@ async def cmd_play(player: Player, args: str) -> None:
     try:
         intro = await session.start()
     except FileNotFoundError:
+        await session.stop()
         await player.send("error: dfrotz not found. cannot play IF games.\r\n")
         return
     except OSError as e:
+        await session.stop()
         await player.send(f"error starting game: {e}\r\n")
         return
 
diff --git a/src/mudlib/if_session.py b/src/mudlib/if_session.py
index b9cb116..3cf26bc 100644
--- a/src/mudlib/if_session.py
+++ b/src/mudlib/if_session.py
@@ -42,10 +42,10 @@ class IFSession:
     async def handle_input(self, text: str) -> IFResponse:
         """Handle player input. Route to dfrotz or handle escape commands."""
         # Check for escape commands (:: prefix)
-        if text == "::quit":
+        if text.lower() == "::quit":
             return IFResponse(output="", done=True)
 
-        if text == "::help":
+        if text.lower() == "::help":
             help_text = """escape commands:
 ::quit - exit the game
 ::help - show this help"""
diff --git a/src/mudlib/server.py b/src/mudlib/server.py
index ffa197d..8cde532 100644
--- a/src/mudlib/server.py
+++ b/src/mudlib/server.py
@@ -353,6 +353,9 @@ async def shell(
             if _writer.is_closing():
                 break
     finally:
+        # Clean up IF session if player was playing
+        if player.if_session:
+            await player.if_session.stop()
         # Save player state on disconnect (if not already saved by quit command)
         if player_name in players:
             save_player(player)
diff --git a/tests/test_play_command.py b/tests/test_play_command.py
index 7d122e2..13bcd02 100644
--- a/tests/test_play_command.py
+++ b/tests/test_play_command.py
@@ -95,6 +95,7 @@ async def test_play_handles_dfrotz_missing(player):
     # Mock IFSession to raise FileNotFoundError on start
     mock_session = Mock()
     mock_session.start = AsyncMock(side_effect=FileNotFoundError())
+    mock_session.stop = AsyncMock()
 
     with patch("mudlib.commands.play.IFSession") as MockIFSession:
         MockIFSession.return_value = mock_session
@@ -114,3 +115,6 @@ async def test_play_handles_dfrotz_missing(player):
 
     # Verify session was NOT attached
     assert player.if_session is None
+
+    # Verify session.stop() was called
+    mock_session.stop.assert_called_once()