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You're right, this is weird ; I thought I did transfer a DRM'd ebook from the Mac ADE to my PRS505, but I may have done it on my work machine (which is a Windows XP PC). My bad, then, sorry.
Bu I'm pretty sure I read somewhere that ADE on the Mac worked the same way with the reader than on Windows, which is (IIRC) simply by using the reader as a USB drive (which works perfectly on my iMac). So, it should work...
I'm almost sure that I did this : I authorized my reader in ADE on Windows, then copied the DRM'd file (a PDF IIRC) to the Calibre library, and used Calibre to copy it to the PRS.
Hope you'll find a way, however I think a virtual machine should be a good idea...
Cheers,
David.
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