diff --git a/choreographer/browser_async.py b/choreographer/browser_async.py
index 2b272597..29a36214 100644
--- a/choreographer/browser_async.py
+++ b/choreographer/browser_async.py
@@ -169,20 +169,23 @@ async def _is_closed(self, wait: int | None = 0) -> bool:
 
     async def _close(self) -> None:
         if await self._is_closed():
+            _logger.debug("No _close(), already is closed")
             return
 
         try:
             await self.send_command("Browser.close")
         except (BrowserClosedError, BrowserFailedError):
+            _logger.debug("Browser is closed trying to send Browser.close")
             return
         except ChannelClosedError:
-            pass
+            _logger.debug("Can send browser.close on close channel")
 
         await asyncio.to_thread(self._channel.close)
 
         if await self._is_closed():
+            _logger.debug("Browser is closed after closing channel")
             return
-
+        _logger.info("Must kill browser.")
         await asyncio.to_thread(kill, self.subprocess)
         if await self._is_closed(wait=4):
             return
@@ -206,7 +209,7 @@ async def close(self) -> None:
         _logger.info("Broker cleaned up.")
         if self._logger_pipe:
             os.close(self._logger_pipe)
-        _logger.info("Logging pipe closed.")
+            _logger.info("Logging pipe closed.")
         self._channel.close()
         _logger.info("Browser channel closed.")
         self._browser_impl.clean()  # threading this just seems to cause problems
diff --git a/choreographer/utils/_tmpfile.py b/choreographer/utils/_tmpfile.py
index 339ab05d..abdbc104 100644
--- a/choreographer/utils/_tmpfile.py
+++ b/choreographer/utils/_tmpfile.py
@@ -185,10 +185,13 @@ def remove_readonly(
             _logger.info(f"shutil.rmtree() failed to delete temporary file. Error {e}")
 
             def extra_clean() -> None:
-                _logger.info("Extra manual clean waiting 3 seconds.")
-                time.sleep(1)
-                _logger.info("Extra manual clean executing.")
-                self._delete_manually()
+                i = 0
+                tries = 5
+                while self.path.exists() and i < tries:
+                    time.sleep(1)
+                    _logger.info(f"Extra manual clean executing {i}.")
+                    self._delete_manually()
+                    i += 1
 
             # testing doesn't look threads so I guess we'll block
             extra_clean()