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I've bought some new e-books and they're in my Digital Editions, and I can open them in my ADE just fine. I've transferred e-books to my Icarus GO reader via ADE in the past, and it worked. Now, however, when I transfer these e-books and try to open them on my reader, it tells me that it failed to open the file. My reader is authorized to my ADE account, there's no issues there as far as I know, and it used to work just fine. I'm not sure how to fix this. I'd rather not read these books directly via ADE on my pc screen, it hurts my eyes.
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Digital Edition and your Reader authorize with the same Adobe ID?
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Yes.
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You can open the file with Digital Edition?
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Yes, I said so, "I can open them in my ADE just fine."
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Seems a problem with a transfer or the Reader itself. Have you try to transfer a eBook out a other source. For example the sample files: Sample eBook Library | Adobe Digital Editions