Put iTunes Music on a Zune MP3 Player
"I purchased about 300 songs from iTunes. I just got a new Zune MP3 Player and I can't figure out how to get my iTunes songs on my Zune. I really don't want to have to buy all these songs again."
Unless you purchased songs from iTunes very recently as iTunes Plus files, your iTunes music purchases are locked down to only work with iTunes, an iPod, iPhone, or Apple TV. There are basically two ways to solve your problem - you can burn audio CDs of all your iTunes purchases and re-rip them using the Zune software, or you can get some help from software that simulates CD burning. Burning CDs can take an extremely long time, while using software works very quickly.
The first step in converting your files is to download SoundTaxi and install it.
Once the software is installed, you simply need to select which files you want to convert, choose a Zune compatible audio format like MP3 or WMA, and wait a few minutes for the software to make all the files playable on your Zune.
After conversion is complete, open your Zune software and import the converted tracks into your Zune music library.