E.g. see [[commons:File:Kassari mõisa valitsejamaja.jpg#filehistory]] or [[commons:File:Vana-Põltsamaa mõisa aia_piirdemüür.jpg#filehistory]]. There are multiple versions uploaded at the same time. As revision history for both mentions no new versions uploaded (though upload log does), I assume these files were uploaded at once.
I haven't tested myself, but probably it was possible because the same title was chosen for multiple images? As images that are overwritten by newer versions are lost and can't be used in Wikipedia articles, I assume this is something that UW sholdn't allow.
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