Hi Andrew, by portrait are you referring to the avatar on a journal? If so, this is a feature of all journals. I've not had any issues adding png files with transparency although I always advise making sure your cursor is in the box for drag and drop even if the transparency makes it looks like the image is outside of the box! Failing that the standard tech help may identify other issues: I'm sorry to hear that you're having issues with the site. Could you please carefully work through 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 and anti-virus programs. 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!