@mkeaton after talking to the team I learned that the issue is that the file extension is uppercase. Can you rename or resave the JPG file to have a lowercase extension? ‘image.jpg’ will work, but ‘image.JPG’ causes issues.
I learned something new too!
@SoMol Contact Support is display in bold at the top of our support page and on every support article. Using Google to find phone numbers for businesses is how people end up getting scammed.