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I don't usually use the sharing feature, but I just tried it with a book sideloaded to Amazon's cloud, and it worked fine. It didn't work with a book sideloaded over USB cable, though.
I didn't do anything with the ASIN on either book, so I don't know if that would make it work for the USB loaded book (or not work for the cloud loaded book). I tried this on my Voyage running 5.7.3. I don't have a PW2 handy--it's out on loan right now. I can check it on my jailbroken PW3 that's on 5.7.2.1 if that would be any help.
Shari
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