I just bought a Shuffle to listen to podcasts. I created a smart playlist as follows: - Podcast = True - Date Added in last 10 days - Late date played before last 12 months (to make sure it contains only podcasts that I did not listen) The smart playlist contains 12 podcasts. So far, so good. I then went to the Contents panel on my iPod page and choose Autofill from Podcast, Podcast being the name of the playlist named above. I then click on Autofill and nothing happens. It says sync complete, but my iPod is still empty. I restarted my iMac and plugged the iPod. iTunes autostarts, but no transfer is done. My iPod is still empty. When I manually drag my smart playlist to the iPod, the podcasts are transferred. Why doesn't the transfer occur naturally when I connect the iPod to my iMac. What is going on?