You cannot play media files that you purchased from the iTunes Music Store after you upgrade to Windows Vista
After you upgrade from an earlier version of Microsoft Windows to Windows Vista, you cannot play media files that you purchased from the iTunes Music Store.
Note: You try to play these files in Apple iTunes.
Additionally, when you try to upload a media file that you purchased from the iTunes Music Store to an iPod, you may receive an error message that resembles the following:
Song name was not copied to iPod name iPod because you are not authorized to play it on this computer
For more information on this issue, including potential causes, workarounds, and resolutions, see: Microsoft KB Article KB936649.

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