diff --git a/src/log_pruner.py b/src/log_pruner.py
index a5f35ca8..6d0f9be9 100644
--- a/src/log_pruner.py
+++ b/src/log_pruner.py
@@ -100,21 +100,24 @@ class LogPruner:
     try:
      sys.stderr.write(f"[LogPruner] Removing {session_id} at {resolved_path} (Size: {total_size} bytes)\n")
      
-     # Windows specific: sometimes files are locked. 
-     # We try a few times with small delays.
+     # Windows specific: sometimes files are locked by the running GUI process.
+     # We try a few times with backoff so transient locks are retried but
+     # the main thread (e.g. hook server startup) is not blocked.
      def remove_readonly(func, path, excinfo):
       os.chmod(path, 0o777)
       func(path)
 
-     for attempt in range(3):
+     last_err = None
+     for attempt in range(2):
       try:
        shutil.rmtree(resolved_path, onerror=remove_readonly)
+       last_err = None
        break
-      except OSError:
-       if attempt < 2:
-        time.sleep(0.1)
-       else:
-        raise
+      except OSError as e:
+       last_err = e
+       time.sleep(0.05)
+     if last_err is not None:
+      raise last_err
      
      # Also remove from registry to keep it in sync
      if session_id in self.log_registry.data: