Windows iTunes Users Should Hold Off On Vista Upgrade
Apple advises Windows users to hold off on upgrading to Vista for "a few weeks" while they resolve some issues with iTunes on Vista. While many users will experience no problems, a few will including the inability to play music or video purchased from the iTunes store, difficulties synchronizing contacts and calendars and possible failures of iPods plugged into a Vista computer.
Update: The iTunes Repair Tool for Vista 1.0 will repair permissions for important files required by iTunes to play your iTunes Store purchases.
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