Pat S. said: Jpegs is not a supported format. They need to be jpgs, pngs, or pdfs. Art library Roll20 supports the following image file types: JPG, PNG, & PDF (upon upload, you'll be asked which page from the PDF will be converted to an image) Roll20 doesn't fully support GIF files due to the inconsistencies and non-standardization of its file type. Some GIF images will upload to Roll20 with no issue, while others will outright fail. Animated GIFs do not work at all on Roll20. I know this is not the problem, but in case anyone reading this is confused or the waters of the question are muddied, the only difference between a jpg and a jpeg is in the name. The file is the same. The issue with using ".jpeg" in a file name is one of Roll20 not accepting the naming convention. Renaming filename.jpeg to filename.jpg can solve many problems.