hmm.. I downloaded your image and dropped it in a game, it uploaded fine for me. What OS and Browser are you using? I suggest following the Bug Report Steps: Bug Report Template Detailed description of the problem Minimum number of steps to reproduce the problem Description of setup Browser + Version Browser Addons/Extensions Operating System Bug Triage Results Please carefully work through to the first three 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 succeed in resolving the problem, please thoroughly work through Step 4 . (Don't forget the complete Console Log!) Supplemental Information Including screenshots by using the "Attach a File" link when submitting a post can provide a great deal of information! The more information you can provide, the better able a fix will be reached.