There is a setting in the Confluence General Configuration on the Admin pages that sets the max size for the attachment. The default is significantly less than that. I noticed the same that it would APPEAR to all get there and then fail. I suspect is buffering in a copy location in the DB and then stores once the transmission is complete.
Anyway, if you change that setting, you'll be good. I have had a couple of occasions where a very large file needed to be placed. That is a HUGE size so I set it up high enough for the file to get loaded and then set it back to something reasonable (15MB) after it's there so there is some measure of control on the size of the files stored on the site.
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