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Transparency isn't possible on most ereaders.
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Bummer.
Do you think there's a way to work around it with my idea of multiple images and selecting on based on the eReader's background color?
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Also epubs of any kind don't work on Kindle. Either you or Amazon have to convert them.
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Amazon must be doing it then. I'm using
https://www.amazon.com/sendtokindle and it won't even take mobi files. From what I read, Amazon finally abandoned mobi for epub recently. But maybe they still use mobi under the hood.