Does "Automatically fill free space with songs" refill the iPhone regularly

I have a bit of music I'd like to have it shuffle, and having it essentially use the autofill command every time I sync my iPhone would be a bonus.
So when you choose "Automatically fill free space with songs" in Sync Music, does it refill the iPhone's music regularly, or do you need to uncheck, sync, and check again in order to keep the autofilled music from stagnating on the phone?

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

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    Ah, it looks like the solution is here:
    http://discussions.apple.com/thread.jspa?messageID=12209799&#12209799
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    This is a bizarre bug that I can't figure out. The "Automatically fill free space with songs" option on both my iPods and my iPhone will only select from songs that were in my iTunes library as of November 2009, about 7 months ago. I know this because I began importing a large portion of my CD library at about that time, and have been expecting to be hearing some new material (like the entire Beatles box set). Instead, I'm getting replays again and again of songs that I know were in there from before 11-09.
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    Ah, it looks like the solution is here:
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  • When iTunes automatically fills free space with songs....

    When iTunes automatically fills free space with songs, where are these songs listed?
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    When iTunes automatically fills free space with songs, where are these songs listed?
    Under Songs, Artsts, Albums, etc.
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    I am very nearly at my limit, so been deleting a few playlists but as I was doing that, it seemed to be filling back up again just as quick.
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    So I deselected the 'Automatically fill free space with songs' button, and the capacity has stayed exactly the same
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    Using iTunes 10.1.0.54 on Windows 7 I've encountered an issue when using the "Automatically fill free space with songs" option with any of my iPod devices.
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    you can report bugs to Apple via this site.
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    Hi,
    When I select "Automatically fill free space with songs" my ipod touch then goes over capacity by .01gb.
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    Ah, it looks like the solution is here:
    http://discussions.apple.com/thread.jspa?messageID=12209799&#12209799
    And involves going to the summary tab, selecting "manually sync music" then deleting all of my songs and resyncing. That shouldn't take more than 45 minutes. I'll report back if it works.

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    You'll probably need to backup or clone the remaining OS X partition, definitely clone the bootcamp partition then erase and reformat the drive. You'll need a 3rd party app.
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    http://manuals.info.apple.com/MANUALS/1000/MA1565/en_US/iphone_user_guide.pdf
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