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Is there a certain limit towards the file size of uploads? I've been trying all day to upload a certain map (Amber Temple from Schley Stack, it's 16.5mb big) but the uploader won't budge at all.
You can scale the map down in an image-editing program (e.g., Photoshop, Paint.NET, GIMP) to a much smaller size without a noticeable loss of quality in Roll20. Try saving the image scaled down to various levels, starting at 25% of the original size. You don't need print-quality images when using them online.