I'm really hoping someone else has this problem and can email me a solution. My sanity is in your hands.
I'm having a bit of a problem with my Xbox 360 as it relates to the music on my iPod. It seems that the console took a bit of a "snapshot" of my iPod when I first connected the two for our Labor Day party and now, no matter how many songs I add to the iPod, no matter how many new playlists I create, and even if I rename the iPod, everytime I reconnect the two the X360 only sees the music and playlists that were there back in September.
I've since added a fair number of songs and albums, created new playlists, and even renamed the iPod device in iTunes in hopes that it would cause the game console to refresh, but no. None of my new content appears in any of the search fields on the X360 dashboard display and none of my new playlists even show up on the list. It's as if my console grew very attached to the order of things back on Labor Day and doesn't dare want to allow them to change. I've tried rebooting the iPod while it was connected; I've tried logging out of my gamer profile and seeing if that would cause it to see it for the first time, and I've even rebooted the X360 while the iPod was connected, but nothing seems to matter.
Please let me know if this has ever happened to you and what you did to fix it. Thanks.