That's actually what I've been trying to do. The playlist I've been trying to sync is strictly composed of podcasts. And to quote, straight from Apple's technote: "The Autofill feature of iTunes will not add audiobooks and podcasts to iPod shuffle." On Aug 28, 2008, at 9:00 PM, Bernard Munter wrote: > One workaround is to put your new podcasts into a playlist of their > own, as > if they were music, and sync the Shuffle from that. People > sometimes do that > so the podcasts play in order on a regular iPod.