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Sony's Mac version only supports the PRS-505 and above. Even after the PRS-500 update, the software still did not support the PRS-500. They also did not support the 500 under 64 bit windows, and I don't know if they've rectified that (or Win7 support for that matter).
While I, too, am disappointed with this, I would pull short of ragging on Sony. It's an old Reader, and obviously uses a different technology for connecting to the computer, and supporting this old connection protocol may simply not be worth the time (consider how slow they are at general updates as it is!). But even so, they offer a free hardware ePub upgrade to PRS-500, which is pretty-much unheard of in the industry. If anything, they deserve kudos for their support of the PRS-500, for that one thing alone! (Yes, I realize you aren't eligible.)
And as has been pointed out several times now, you can use Calibre with the PRS-500. You don't need the Sony Reader Software at all. There are other older solutions that also allow you to copy files to your PRS-500 from the Mac. So the gap in Sony's lack of software support has been filled pretty readily by 3rd parties. And they arguably do a better job anyway!
-Pie
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