Corollary to the thread on reuploads, I think I just stumbled into an edge case where an interrupted submission is locking out further uploads:
The other day I had prepared an image for submission, only to suspend the final upload to preserve the original gallery order, and some time later I navigated away from the page by mistake. Trying to submit the image now, the file successfully uploads (100% with green outline), but attempting to post prompts a popup error "Your uploaded file seems to be missing. Please try uploading it again."
My best guess is, the file itself is on the server, but because the initial submission wasn't completed, it's orphaned in the database and is preventing uploads with the same filename. tl;dr if you have to abort a submission, cancel the upload first.
For reference, original file is named Catch That Obergruppenführer.gif,