Currently Being ModeratedMar 24, 2013 10:35 AM (in response to MTAapple)
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
Currently Being ModeratedMar 24, 2013 12:14 PM (in response to MTAapple)
Not sure why that happens... Check the Settings button next to the Autofill button. If it's not checked already, try checking the box for Replace all items when Autofilling. Also, make sure the the slider for Reserve space for disk use is set to zero (or a setting that allows space for loading songs).