Sounds familiar, First check here, see if your Storage Quota is full: <a href="https://app.roll20.net/account/" rel="nofollow">https://app.roll20.net/account/</a> If it's full you can go into your Art Library and start deleting the old ones, to free up enough room. (Or upgrade to Roll20 Plus or Pro, that gives you larger quota space). NEXT Just so you know, there's a different Roll20 feature designed to change your Character Picture for each game, and you only upload once. You don't upload a new Character picture onto your Roll20 Profile avatar picture. Normally you just upload that picture once, to your Character Sheet or Character Journal within the game that you're playing. After that just use the drop-down menu at the bottom-right (below the chat), called the "As" dropdown, and change it to your Character there, so that your avatar portrait will switch to appear AS your character. This doesn't work in every game --- it doesn't work if the game has Roll20 Video tech enabled. If your storage quota is NOT full then you've encountered a different problem/bug --- post again