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Sounds like you recorded the songs in WMA format with DRM (digital rights management) enabled. Those songs are now copy protected and you will have to jump through hoops to use them on anything but the machine they were recorded on. Also, you mentioned deleting some things...if one of those things was the folder containing your DRM licenses, you won't even be able to play those on your computer let alone transfer them to your PocketPC. Your best bet is to rip the music again with copy protection off.
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