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Welcome Lizzy. Been too many iterations since I use my PRS-500 and there have probably been some changes. That said, you might try using Calibre (see the WIKI pages here on MR). I understand that it might be easier to use than the Sony Library SW.
Back in the old days, you could just drag the book from the hard drive to the Sony Reader using the Sony SW. However it did not work in reverse (i.e. from reader to hard drive).
Good luck & you'll probably get some better answers soon from more knowledgeable people.
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