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I've been trying for a few hours now to upload map images into my game. This includes both png and jpg images and this also includes me going between firefox, chrome and explorer to see if there's a difference.
How big are the images in bytes? As a Pro user your images are limited to 10MB in size. Check your Storage Quota (<a href="https://app.roll20.net/account/" rel="nofollow">https://app.roll20.net/account/</a>) and see if it is full. As a Pro user you have 6GB of storage, so it is not likely that is full, but it is possible if you have uploaded a lot of sound files.
I don't think you can upload textfiles... I have never tried. Your best bet would be to open a handout to edit, copy and paste the text into the handout, and then save it.
I tried it and it didn't seem to change anything. Something I did notice is that if I'm quick enough after loading a campaign I can sometimes manage to load in one image as long as it's fairly small (so usually doesn't work for maps unless piecemealed but it works for a single token) but then afterwards uploading images doesn't work.
