When the ipod is shut off for long enough to forget your place, it will not resync even when you click the headset in the setup screen. You have to re-pair them to use the bluetooth headset. If you just shut off the ipod and headset for a few minutes to an hour, it comes back on just fine. If you wait until the ipod forgets where you are and you have to go back into music and re-select stuff, it will not find the headset no matter what you do. You have to "forget this device" and then re-pair them. On the same set of headphones, they pair with my phone every time no matter how long it's been off or what else is going on. Same with macbook pro and ipad. It's only on the ipod and only if you leave the ipod off long enough to forget where you were in the playlist.