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Erm, I don't know which OS you're using (if it's Windows, please ignore!) but if you've got a Mac, it won't recognize your reader, and as far as I know there's no way to make it do so. You can, however, still manually drag files onto the reader (from documents --> Digital Editions) and transfer everything that way.
I spent a couple very frustrating hours learning that when I first got mine, heh heh...
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