Does the "Fill free space with music" not work like it did before?

Before updating my iphone 4 to iOS5, the fill free space with music seemed to rotate in and out music and also provided space to add more pictures, podcasts, etc.  Now it just seems to fill the phone to the max on the first sync and just leave what it put on there in place.  If I try to add something like a folder of pictures it will only add a few of the pictures because there is no room.  Before I think it freed up room by deleting some of the "free space" music.  I'd like to go back to that.  I really don't want have to had select every song I put on the iPhone when I have more music than my phone will hold.

Also, how does it decide what to add to the iPhone?

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