Is it maybe too big? That's the main reason I get that message when trying to upload pictures to the site - I have to resize the picture a bit in Paintshop (usually reduce to 70%ish of the original size) and then it seems to work.
If it keeps saying failed file it sometimes helps to put it on like tinypic.com, then use "Upload File from URL" instead. It was happening to me awhile back, but my file type was fine and so was the size
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