Hi DM Ben, This definitely sounds... odd. Would you mind sending in a support ticket via Roll20.net/help and attaching the file you are attempting to upload? Further, if you could make sure to include a link to this thread so we know its you :) I'd like to see if we can reproduce on our end and get this to our dev team to take a look. Some things you may try in the interim is test converting to a different file type -- its a long shot but worth a try! EDIT: Typo