Hi Banquo! Some questions and things to try: 1) have you checked your storage quota on your accounts page? Audio eats up space fast. 2) What is the format and size of the audio file you are uploading. Not all are recognized. Roll20 supports four audio file types: MP3, OGG, FLAC, and WAV, with all audio uploads having a maximum upload size of 20MB each, although that 20MB limit might be outdated. 3) You can try deleting cache and cookies, then logging out and back in again. You could have some bad cached data or code. You could also test with an incognito/private browsing window, or a different browser all together. That should rule out most possible extension conflicts. 4) Have you tested with a different file, to rule out the possibility of corruption in your audio file? If none of that yields any results, your best bet is to capture a Console Log ( Chrome , Firefox ) and file a Help Center Request to get team member attention.