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Not sure what to suggest now.
Have you got calibre working? Does that detect your reader?
If you have books that don't have DRM (eg from MobileRead or other free sites) you can treat your reader like a memory card or hard drive and transfer files onto your reader that way.
You could also try posting onto the main Sony 500/505 forum and asking if other mac users can help you as they may know something easy that will sort things out for you.
Sorry it didn't work!
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