Be sure that you are deleting images from the Recent Uploads section of the Art Library. Just deleting them off maps and pages does not remove them from your Storage Quota. See the wiki here: <a href="https://wiki.roll20.net/Art_Library#Freeing_Up_Storage_Space" rel="nofollow">https://wiki.roll20.net/Art_Library#Freeing_Up_Storage_Space</a> Similarly for audio, removing them from Playlists does not remove them from your Storage Quota. From the main Roll20 menu, click Tools, then Manage Audio. Click the Tracks tab to see audio files associated with your account. If you delete them from here, that will free up space. Also, be sure that the image file you are trying to upload is less than 5MB in size; free users are limited in that no one image file can be larger than 5MB.