iPod Smart playlist does not transfer to Shuffle

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?

theLimit said:

The 1st gen Shuffles ignore podcasts and audiobooks when using Autofill, which I find quite annoying. Maybe the 2nd gens are the same.

Click to expand...

Oh, that is a bummer. I bought the Shuffle to listen to podcasts.

Looks like I found a turnaround solution:

http://www.macosxhints.com/article.php?story=20070218041737189