If you're like me, you are frustrated by how this is seemingly impossible. Microsoft wants you to buy a PC with Media Center Extender to do any kind of media streaming, and Apple won't let anyone else parse its DRM-protection. Argh! I bought the music (instead of stealing it), why won't you let me enjoy it??!!! Well, with enough determination, I think I have found a decent workaround that is both convenient and relatively inexpensive. It's like AirPlay, but for Xbox 360. Here are the limitations: 1. You still need a computer running (would be nice to throw an itunes library on a NAS box and be able to decode it on the fly through the Xbox 360, but alas, no). 2. As of now, I've only figured this out for audio (music, audiobooks, podcasts, etc). No video (tv episodes, movies, video podcasts). Here's what you'll need: 1. Mac with iTunes 2. Xbox 360 w/network adapter 3. Router (to which both of the above are connected) 4. Mac-compatible media server software that can fool your Xbox into thinking it is talking to a PC. I use Connect360, but I've heard of others (e.g. Rivet, which I haven't tested). Both are ~$20. 5. A way to create a .m3u stream from your iTunes output. I use NiceCast (full version is $40). There may be a free alternative out there, not sure. ----- 6. (For convenience) an iPhone w/the 'Remote' app (free) installed to control what you're listening to, since you will not be able to navigate your library on your Xbox 360 using this method. Steps: 1. Give your Mac a static IP, or reserve an assigned DHCP IP address so that it will always be accessible at the same address. 2. Install NiceCast on your Mac. Set it up to stream your iTunes output to an .m3u file. Take note of its network address (which shouldn't change). 3. Broadcast and test this stream by playing a song in iTunes, opening a browser and navigating to the stream URL. If it works, save the .m3u file to your desktop. 4. Create a new playlist in iTunes called "Library Stream" (or whatever you'd like). Drag the .m3u file into this playlist. 5. Install Connect360 and configure it to share your iTunes library. NOTE: A word of caution here, if you happen to use Elgato EyeTV, know that it installs something called EyeConnect for sharing TV captures that can cause some serious problems. It conflicts with Connect360 and prevents it from seeing and authorizing your Xbox. This ate about 3 hours for me. Here's how you can completely remove it. 6. Once Connect360 sees your Xbox and the connection is established, head over to your Xbox 360. Go to My Xbox -> Music -> select your Connect360 connection as the source and choose the playlist that you set up earlier (with the m3u stream in it). You should now be able to hear whatever your mac is playing in iTunes. The cool part - this works even with DRM-protected songs! 7. Last step - since your mac is controlling what is playing, you'll want a convenient way to change songs, pause, advance, etc. Since I have my iPhone on me constantly, I use Remote to remotely control iTunes. Airplay let's you control playback on all kinds of Apple devices, but now you can have similar control over playback on your Xbox 360. This way, the computer can be elsewhere and you can control what's playing while you are at the 360 (perhaps while you frag some n00bs). The app is free, and also available for iPad. EDIT: To automate things a bit more, set NiceCast and iTunes to open at login. Then go to System Preferences -> Accounts -> Login Items and minimize all of them (so you aren't bombarded with open windows every time you turn on your computer). In NiceCast preferences, set it to start broadcasting at launch. Enjoy what you rightfully own, the way you want to. PS - if anyone figures out how to use a similar setup to access protected video content, let us know by posting a reply in this thread with instructions!