If you upload a new version of a file, then look at the File history section, the new version will still be showing the old thumbnail. I assume this is some kind of cache invalidation failure. See first attached screenshot was taken about an hour after I uploaded the new file.
I could force the correct thumbnail to show by reloading the page with Shift-Reload (second screenshot).
https://en.wikipedia.org/wiki/File:Twinkle_XFD_Menu_Screenshot.tiff
I'm using:
Chrome Version 76.0.3809.132 (Official Build) (64-bit)
MacOS 10.13.6 (17G8030)

