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Sort of. I've followed the directions from the iPod support site several times on both my laptop and desktop. It finally seemed to work, allowing music to transfer but won't play. I've given up. I got got and it's my fault.
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If you haven't yet, download the latest Shuffle software and try restoring the Shuffle. This is in effect a "hard reset" bring the Treo back to it's initial state.
Here's a
related thread on the topic.
Good luck.
-Chris