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i have a map that wont upload. its a 1.1mb jpeg. i'm trying to drop it into a handout. a grey bar appears like its attempting to show the load bar but it doesn't. 
One thing you can try is change the filename to end with .jpg instead of .jpeg. It was a long-standing bug that Roll20 would not accept the .jpeg file extension, but it was reportedly fixed a few months ago. You might want to give it a try, all the same.
Hey Edward G. -  Just checking in here, did the advice provided by Rabulias above help you get this figured out? Or did you still need some assistance?