I will show you how to use TwonkyMedia to play music from your iTunes library on your Xbox.
Note: **This DOES NOT work with music you bought directly off of iTunes**

1.First you need TwonkyMedia. I have provided a link to the download w/ crack.
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2. Install TwonkyMedia by clicking on the setup.exe I provided. When installing place the media root directory in "C:\Documents and Settings\Owner\My Documents\My Music\iTunes\iTunes Music". Or wherever your iTunes Music folder is. Install the main program files where it is set to by default. **If you do not have an iTunes Music folder than skip to step 7 and then come back to this step and go on**



3. Now in the download you should have gotten a folder called "crack". Replace the file in C:\Program Files\TwonkyMedia\ with that file in the crack folder. Done, now you should have a working server.
**Make sure TwonkyMedia is not running at all when you replace the file**



4. Now open TwonkyMedia. If it does not open a tab in your browser than click on the "Open Configuration Page" on the quick access button on the taskbar.



5. On the configuration page click on the tab on the left "First steps" then pick a language, make a server name (doesn't matter what it is), and then leave the last one as default. Next click the tab on the left called "Clients/Security". Click on the drop down box under the preset "twonkyplayer" already there. Click on Xbox 360. It should not have the IP Address for the Xbox yet. That's it for that you can close out of the configuration page. Picture for help:
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6. Open iTunes and on the top right click File - Library - Organize Library...
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7. Check both boxes. If you can only check the first one than you have already done the second one in the past. Click "OK" and wait until it is finished.



8. You are finished on your computer. Now head to your xbox and go to My Xbox / Music Library and click on the last one. It should say PVConnect with your Server name you picked in front of it. If you click on that you should be able to see your ENTIRE iTunes library, playlists and good stuff like that.

I hope I helped and if I missed anything, or you need help PLEASE post below.