fix: improve cleanup error handling in CopilotClient and CopilotSession to propagate errors correctly

Author: Sumanth007

python/copilot/client.py

@@ -14,7 +14,6 @@
 
 import asyncio
 import inspect
-import logging
 import os
 import re
 import subprocess
@@ -238,8 +237,10 @@ async def __aexit__(
         Exit the async context manager.
 
         Performs graceful cleanup by destroying all active sessions and stopping
-        the CLI server. If cleanup errors occur, they are logged but do not
-        prevent the context from exiting.
+        the CLI server. If a cleanup error occurs and no exception was raised
+        inside the context, the cleanup error is propagated. If an exception
+        was already raised inside the context, the cleanup error is suppressed
+        so the original exception is not masked.
 
         Args:
             exc_type: The type of exception that occurred, if any.
@@ -250,14 +251,10 @@ async def __aexit__(
             False to propagate any exception that occurred in the context.
         """
         try:
-            stop_errors = await self.stop()
-            # Log any session destruction errors
-            if stop_errors:
-                for error in stop_errors:
-                    logging.warning("Error during session cleanup in CopilotClient: %s", error)
+            await self.stop()
         except Exception:
-            # Log the error but don't raise - we want cleanup to always complete
-            logging.warning("Error during CopilotClient cleanup", exc_info=True)
+            if exc_type is None:
+                raise
         return False
 
     @property

python/copilot/session.py

@@ -7,7 +7,6 @@
 
 import asyncio
 import inspect
-import logging
 import threading
 from types import TracebackType
 from typing import Any, Callable, Optional
@@ -113,8 +112,10 @@ async def __aexit__(
         Exit the async context manager.
 
         Automatically destroys the session and releases all associated resources.
-        If an error occurs during cleanup, it is logged but does not prevent the
-        context from exiting.
+        If a cleanup error occurs and no exception was raised inside the context,
+        the cleanup error is propagated. If an exception was already raised inside
+        the context, the cleanup error is suppressed so the original exception is
+        not masked.
 
         Args:
             exc_type: The type of exception that occurred, if any.
@@ -127,8 +128,8 @@ async def __aexit__(
         try:
             await self.destroy()
         except Exception:
-            # Log the error but don't raise - we want cleanup to always complete
-            logging.warning("Error during CopilotSession cleanup", exc_info=True)
+            if exc_type is None:
+                raise
         return False
 
     @property