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2. Roll20 has a maximum filesize of 5 MB for images you upload to them, and a total upload limit of 100 MB across images and audio. Make sure your image is under 5 MB or else it will just fail without any kind of notification. If your file is too big, use an image compressor, there are plenty of them online that will let you upload your image, compress them on the site, and download the new version.
Make your map
Save as JPG
Open Roll20
On left side click the cube icon then click "map and background"
Drag and drop your map onto Roll20
Adjust the map so that it fills the Roll20 background
Done! Just be sure to click the cube again and click "Objects and tokens" to place tokens.