Can't get iTunes to Autofill from a Smart Playlist

I think the subject line says it all: I can get iTunes to Autofill my 1GB shuffle from a manually created playlist, from the main Library, or from my Purchased Music but if I use a Smart Playlist as the source of the Autofill I get nothing but a blank stare--nothing changes--it doesn't even flinch. What am I missing?
I have restored the shuffle using the 1.1.2 firmware update and it still doesn't work. It has been this way with every version of iTunes I've used since I got the shuffle up until the current version, iTunes 5.0. I'm currently running Mac OS X 10.4.2 with 1.25GB of RAM on a PowerBook G4
Any help would be appreciated.

I have practically the same problem, but only with podcasts. From a smartlist having all my podcasts, autofill only puts two onto the shuffle. From a normal playlist, none. I can drag them all into the shuffle. I'm on an iBook with Panther, iTunes 6, September 2005 iPod updater.

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