diff --git a/pkgs/clan-app/clan_app/middleware/logging.py b/pkgs/clan-app/clan_app/middleware/logging.py
index e356e8034..d7f936d9d 100644
--- a/pkgs/clan-app/clan_app/middleware/logging.py
+++ b/pkgs/clan-app/clan_app/middleware/logging.py
@@ -1,5 +1,7 @@
 import io
 import logging
+import os
+import sys
 import types
 from dataclasses import dataclass
 from typing import Any
@@ -91,12 +93,18 @@ class LoggingMiddleware(Middleware):
                 exc_val: BaseException | None,
                 exc_tb: types.TracebackType | None,
             ) -> None:
+                orig_stderr = None
                 if self.handler:
                     self.handler.root_logger.removeHandler(self.handler.new_handler)
                     self.handler.new_handler.close()
                 if self.original_ctx:
                     set_async_ctx(self.original_ctx)
+                    orig_stderr = self.original_ctx.stderr
                 if self.log_f:
+                    # Replace the file descriptor instead of closing it
+                    stderr = orig_stderr or sys.stderr
+                    new_fd = stderr.fileno()
+                    os.dup2(self.log_f.fileno(), new_fd)
                     self.log_f.close()
 
         # Register the logging context manager