When I upload a new version of this file, it keeps the old version as the current version and puts my new version as the previous version
No. It's just a caching issue. The image on the page will be updated later.
Thanks for your patience.
Not sure about that... I'm referring to the thumbnails on the file upload page, and I did the update yesterday but its still wrong today. Other files I've updated have worked fine straight away. Anyway, I'll give it a bit longer.
From my understanding, when you upload a new image and the displayed size change a new image is generated and immediately displayed. When the new image has the same dimension has the old image or the image is displayed with a fixed width, when the cached image is used. In this case, we need to wait around two weeks to see the cache invalided and the new image displayed.
Hope this help.