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I don't believe you can b/c it's all Apple proprietary **bleep**. That's one reason I won't own an iPhone or iPod. Some phones are actually locked from iTunes from what I read. Please read this article as it may clarify some things for you, but I think you're **bleep** at this time as Apple does not guarantee player compatibility with non Apple producs.
For more info ---> http://arstechnica.com/apple/news/2009/06/apple-warns-about-itunes-syncing-with-non-apple-devices-1.ars
-JustinA "Quickpull" a day keeps the lag away. Get it here---> http://software.crackberry.com/product.asp?id=27660&n=QuickPull-v2-(BETA)Serving proudly, USAF, Land of the free because of the brave.
Rim offers a free program called, if I remember correctly, Media Manager. It interfaces quite nicely with iTunes and will load any unprotected tracks you want onto your Tour. You just have to put things into a playlist first. It's actually quite a slick little program.
Best of luck.
Thats if he didnt get one of the Tour disks that don't work. If you didnt get DM5.0 disk dl here
http://vzw.smithmicro.com/blackberry/desktop.aspx
