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Which phone do you have? My experience with DRM-encrypted WMA has been:
With my Motorola MPx200 and any DRM-WMA, with the phone runnning WM2003 and thus WMP9, the files will not play despite my transferring them via WMP on the PC unless I transfer them to main memory.
However,
with my i-mate Smartphone2, all DRM-WMA files transfer and play flawlessly (to SD or to main memory); the Smartphone2 is running WM2003 and has WMP9 as well.
I can't find any explanation for it; I've used MusicMatch and Napster and the same holds true for both.
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Current Toy Bag ~ T-Mobile Dash ~ Apple MacBook (2GHz, 2GB RAM, 160GB HDD, SuperDrive) ~ 30GB iPod ~ Canon MP500 ~
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