In addition to bug 43320, in the following step the UW failed to identify that the auto-entered filenames where identical and upon confirmation went to the next step, uploading three files under the same title (see URL).
After the third upload it realised the mistake and told me "There is another file already on the wiki with the same filename" for all the other files, offering to edit metadata for them.

Version: master
Severity: major
URL: https://commons.wikimedia.org/wiki/File:Scribe_Machine_Acquisition.jpg
See Also:
https://bugzilla.wikimedia.org/show_bug.cgi?id=54750
https://bugzilla.wikimedia.org/show_bug.cgi?id=43320