'Automatic' filling of free space

Maybe this is more of an iphone question, but hey. My question is, when I am syncing my iphone with itunes, and I select a few playlists which have a total size of 1.4gb, and then when I instruct itunes to 'automatically fill space with songs' - which, to my mind, should be a random selection - and that free space is some 13gb - I seem to always have the same songs! Is there a way I can make the selection more random? I have nearly 8000 songs in itunes, yet seem to hear the same 100 on my iphone?
Thanks!

I see that there are many similar discussions here, but no-one seems to have resolved this...? Anyone?

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