Smart Playlists – “Live Updating” on IPOD

So, In iTunes, I have created a few smart playlists – playlists that update on specific criteria – and set the live updating
flag so each playlist is updated as contained songs are played (my
playlists contain the least recently played 100 tracks).  Only
problem is that the live updating feature doesn’t appear to work on my

A little Google searching found me a page on the Apple web site, where
Apple admits breaking this feature with the June ’05 software update.