I'm having the same problem as others in this thread . . . and I do not manually manage music and videos. I use smart playlists, only sync checked items, etc.
I have noticed the problem happens only with songs I buy from iTunes on my phone. Here's what happens:
1. Buy song on phone.
2. Play however many times.
3. Sync. Song copies to computer with a play count, as it always did before iOS5.
- I don't use the cloud and I don't use automatic downloads. Because when I did, the downloaded song on my computer would also copy to my phone, and I'd have two copies of the song, neither of which synced playcounts. Not what I'm after.
4. Move off iPhone's screen in iTunes. Get warning (that does not go away, despite my trying out the tips in another thread) about my having changed settings (I haven't), do I want to apply the changes, etc. I say yes and eject.
5. Go about my day or week. Play various songs, including my recent purchase.
6. Sync again. All playcounts will sync except . . . the recent purchase.
The only way I've found to get around this is to:
1. Buy
2. Sync
3. Delete song from iPhone
4. Sync again, with song copying from computer back to iPhone
It works. But it's a really stupid workaround.
This problem began with iOS 5. And again: I am not manually managing anything. With that factor removed, does anyone have any ideas?