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Depending on how old the reader is you may have some files that are LRF or LRX. If so, you should be able to download the purchases again from the Sony Store with the EPUB extension. I also find it is much easier to use Calibre to upload books to either Bluefire, or iBooks instead of iTunes. Just use the Calibre Server, and go to the IP address of your server using Safari, and then choose open book with either iBooks or Bluefire. It will then add the book to your library. Hope this helps some.
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