How to reshuffle my Shuffle?

I fill my iPod Shuffle 4 from a playlist that has many more songs in it than the Shuffle will hold.  So, when I plug in (iTunes on Windows 7), I like to reshuffle and get a new selection of songs.  That always worked fine with my iPod Shuffle 2 (I think it was called "autofill"), which recently died, but now that option doesn't seem to be available.  If I click Sync, nothing happens, it just tells me that I am "over capacity."  I do have the box checked for "automatically fill free space with songs."  What am I doing wrong? Thanks!

Autofill is available on the new shuffle as well, just in a difference place.
To use Autofill, first select the shuffle in iTunes and go to the shuffle's Summary screen.  Set it to Manually manage music, if it is not already, and Apply the change.
In the iTunes sidebar (which may be hidden in the latest iTunes), select the shuffle under DEVICES, and show (drop down) its contents.  You should see Music under the shuffle there.  Select it, and over to the right, there is a listing of songs currently on the shuffle.  At the bottom of the listing, you should see the settings and button for Autofill.
NOTE:  If you want to use automatic syncing, you can post back.
This document has more info on syncing the shuffle
http://support.apple.com/kb/HT1719

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