Hello Dylan L., I'm sorry to hear that you're having issues with uploading photos. To rule out any potential issues, we ask that you please carefully work through these steps of our guide to Solving Technical Issues ? Step 1: Make sure to use the right browser Please check if these issues persist when using both Chrome and Firefox. Step 2: Ensure that there are no extensions/addons interfering with Roll20 Please disable all add-ons/extensions. Step 3: Clear your cache If none of the above succeeds, please thoroughly work through Step 4 . (Don't forget the complete Console Log!) Thank you!