I just uploaded something successfully. You might want to try again, and if it doesn't work you will probably need to provide more information (browser used, whether you tried both supported browsers in case it was a browser issue, file size, file type, console log, etc.) and probably send it through the Help Center ticket system. <a href="https://roll20.zendesk.com/hc/en-us/requests/new?ticket_form_id=360004417173" rel="nofollow">https://roll20.zendesk.com/hc/en-us/requests/new?ticket_form_id=360004417173</a>