When I upload a file in one of our wikis, embed it in a wiki page and then upload an updated version, the the file details page shows the new version, but page where I embedded it still shows the original version.
This is a problem especially for human interface guidelines, where we often have to update screenshots to reflect design changes. Of course as a workaround I can upload the new version under a new name and change the wiki page, but that's extra effort which adds up over time, and leaves us with lots of unlinked files over time.