iTunes 11 won't sync/autofill; not enough free space.

I follow the support thread for 4th Gen iPod Shuffle looking for "autofill" instructions... it winds its way to instructions for iTunes 10. I know how to do it in 10, but I hav 11 now and it doesn't seem to be the same. I do get the option to sync the ipod but now I get the error "Not enough free space to hold all of the selected items." That is the point. I want it to randomly autofill my 2GB iPod from a selection of songs that is significantly larger than that. That way, I get some fresh songs rotated in when i sync. In v10 I used to get that error but I could say "Okay" and it would randomly choose from the list until the iPod was full. Now it just doesn't do anything. It makes me sad to think of all the time I've spent trying to keep this $50 player useful, and that autofill from a vast library feature is the entire reason for the Shuffle's being.

I sort of hope the answer is right in front of my eyes. Sort of.

Thanks in advance for any blindingly obvious answers and/or words of comfort you might have. ;-)