I have a 16GB iPhone. I manually manage the music (I don't sync). I feed the iPhone with a smart playlist containing a random 10GB of music. In the iTunes library, if I select all the music in the smart playlist and delete it, the playlist automatically repopulates itself with a fresh 10GB. This *was* how I kept a fresh batch of tunes on my phone. Previously, when I used to sync automatically, any change I made to the smart playlist in the library would automatically update said playlist on the iPhone. But now that I manually manage music, the smart playlist on the iPhone no longer gets the updates from the library version. It's like I have 2 smart playlists; one in the library, which is dynamic or smart, and one on the iPhone which is static, or not so smart. The workaround is to drag the dynamic playlist from the library onto the phone, and have iTunes tell me there's already a playlist with the same name and overwrite the existing one. Seems iTunes draws the line at smart playlists on a manually managed device. Is it just me, or doesn't this sort of go against the concept of a smart playlist? If this is the intended behavior, shouldn't iTunes "rasterize" the smart playlist on the iPhone, and just convert it into a normal playlist, instead of keeping the smart playlist icon?