I just purchased two language learning audio courses from the iTune store. Purchased them on my iPhone and they play fine. Now I want to put them on my iPod Shuffle. I created a playlist that contains just these two items. They are both "Protected AAC audio file" types. And as I said, they play fine on my iPhone and in iTunes itself. I plug in my shuffle and select that playlist as the one to fill it from. But iTunes refuses. It give me some BS like "iTunes cannot add any songs to the iPod "iPod Shuffle 1GB" because no songs in the playlist "iPod Shuffle JLearn" can be copied to this iPod." And that's it. I've tried playing with all the options on this shuffle (Replace all items when Autofilling, Convert Higher bit rate songs, etc.) to no avail. iTunes just refuses to copy them. And worse, it won't tell me why (this is straight out of the Microsoft play book Anyway if anyone has seen this before and can offer any clues, I'd be grateful. Are there restrictions on what can be put on a shuffle??? Why do these tracks work on my iPhone but not on the shuffle? I've used this shuffle for a long time now and have frequently filled it with various music. But this is the first time I have tried a "Protected AAC audio" file. If that's the reason, why on Earth would Apple do that? So I can't play audio I bought, on my own iPod??? Yeah, I know, I should try burning them to CD and then reimporting them. But since I moved all my blank CDs are in some unknown box in some closet somewhere...!