ITunes 11 Autofill Not Working On iPod Shuffle

I had to reinstall iTunes 11 following a reinstall of Windows and now iTunes will no longer "Autofill" my iPod Shuffle.
Formerly, Autofill would randomly refill my iPod Shuffle with tunes from my iTunes library, but it no longer wiill.
When I select "Autofill" the status bar at the top indicates it has begun a synchronization and iTunes seems to "hang" at that point. I am never presented with the screen showing the "random" tunes selected or showing them being updated on my iPod Touch. After some bit of time, iTunes reports that it could not add any more songs to my IPod Shuffle because there was no more space on it.
As of now, my iPod Shuffle is "stuck" with the tunes it had on it before I reinstalled iTunes as part of a Windows reinstall..........the Autofill feature of iTuned 11 doesn't appear to be working.
I've worked on this for hours and hours and tried every combination of settings I can think of with innumerable reboots to have Windows 7 re-recognize the iPod Shuffle. (It disappears following the "hang" of iTunes 11. I'm out of ideas and have no more time to expend on this. Oh....and it will not let me reset my iPod Shuffle back to factory state eitehr.
QUESTION: Does anyone know how to "fix" this............or is this a bug in the current release of iTunes 11?

Hello,
I have the exact same problem as you do. I tried updating iTunes to the latest version (10.0) and my iOS on my iPod Touch (2nd generation, 8GB) to the latest version (4.0.2) and unsyncing all of my apps to see if they were conflicting with the top tens list somehow. However, my top tens list is still blank/empty.
Let me know if you find a fix.
Thanks

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ITunes 11 Autofill Not Working On iPod Shuffle

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