diff --git a/.jules/bolt.md b/.jules/bolt.md
index d81dff90..f1595cb4 100644
--- a/.jules/bolt.md
+++ b/.jules/bolt.md
@@ -1,3 +1,6 @@
 ## 2025-05-15 - [Sequential session destruction in SDKs]
 **Learning:** All Copilot SDKs (Node.js, Python, Go, .NET) were initially implementing session destruction sequentially during client shutdown. This leads to a linear increase in shutdown time as the number of active sessions grows, especially when individual destructions involve retries and backoff.
 **Action:** Parallelize session cleanup using language-specific concurrency primitives (e.g., `Promise.all` in Node.js, `asyncio.gather` in Python, `Task.WhenAll` in .NET, or WaitGroups/Channels in Go) to ensure shutdown time remains constant and minimal.
+## 2026-02-07 - [Python SDK] Parallelize Session Destruction
+**Learning:** Sequential cleanup of network-bound resources (like JSON-RPC sessions) leads to (N)$ shutdown time. Parallelizing with `asyncio.gather` reduces it to (1)$ relative to session count.
+**Action:** Always check cleanup/stop methods for sequential IO and parallelize where safe. Implement retry logic for cleanup to match robust SDK patterns.
diff --git a/python/copilot/client.py b/python/copilot/client.py
index 85b72897..e384ef91 100644
--- a/python/copilot/client.py
+++ b/python/copilot/client.py
@@ -313,13 +313,29 @@ async def stop(self) -> list["StopError"]:
             sessions_to_destroy = list(self._sessions.values())
             self._sessions.clear()
 
-        for session in sessions_to_destroy:
-            try:
-                await session.destroy()
-            except Exception as e:
-                errors.append(
-                    StopError(message=f"Failed to destroy session {session.session_id}: {e}")
+        async def destroy_with_retry(session: CopilotSession) -> Optional[StopError]:
+            last_error: Optional[Exception] = None
+            # Try up to 3 times with exponential backoff (match Node.js SDK)
+            for attempt in range(1, 4):
+                try:
+                    await session.destroy()
+                    return None
+                except Exception as e:
+                    last_error = e
+                    if attempt < 3:
+                        # Exponential backoff: 100ms, 200ms
+                        await asyncio.sleep(0.1 * (2 ** (attempt - 1)))
+
+            return StopError(
+                message=(
+                    f"Failed to destroy session {session.session_id} after 3 attempts: {last_error}"
                 )
+            )
+
+        # Destroy all active sessions in parallel to ensure shutdown time is
+        # independent of the number of active sessions.
+        results = await asyncio.gather(*(destroy_with_retry(s) for s in sessions_to_destroy))
+        errors.extend([r for r in results if r is not None])
 
         # Close client
         if self._client: