OK, by your post, I assume the graphic is of reasonable size (5k is quite small and should never be an issue), that the graphic is a jpg, with the ".jpg" extension, and not the .jpeg extension, which can cause problems, and that you have tried both Chrome and Firefox. If all those are so, l'll post the remaining Troubleshooting steps below. if you still get no upload joy after that, please follow step four and post the log so the dev team can see exactly what's going on. 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 and anti-virus programs. (This can often be accomplished by loading the site in an incognito window) 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!