Hey mhmtn;
If you’re referring to the link in the admin-menu, that is an AJAX-request which can time out. In that case go the the AO settings-screen and click on “save changes and clear cache”.
If you’re referring to the fact that when clicking on that “save changes and clear cache”-button on the AO settings-screen you still see a number of files as being in cache; that is normal as AO will “warm up” the cache by immediately generating and caching optimized JS/ CSS for your homepage.
Hope this clarifies,
frank