So my mom got me a iPod Shuffle for Christmas. It's perfect for me to listen to my podcasts while I am doing work around the house. So I hook it up and do the AutoFill of music and it takes 5 minutes to load the thing up.. that's cool. Works perfect.
I hook it back up and try to load a podcast up (TWiT) and take it out and nothing. The light on the power blinks green and orange for two seconds. I look on the little light indicator cheat sheet it came with and that means there are no songs loaded onto the iPod Shuffle. This made absolutely no sense to me...I tried everything re-encoding it. Loading it onto the shuffle as a data item but it still wouldn't work.
After looking around the internet I found a few people are having a problem with regular iPods playing podcasts in playlists where they had to manually start the podcasts. They found that each podcast is by default flagged with the do not shuffle flag. This meant that the podcast file wouldn't come up when you were playing songs in shuffle mode.
Ah, now it makes perfect sense why this isn't working. The iPod Shuffle works exclusively in shuffle mode so that's why it looks like there is no music on it after updating.
To get around this...select the Podcasts you want to load and right-click (yeah I am on a Windows machine) and check the check box that says shuffle and select yes. If you want to load just one file click on the options tab and click to uncheck the skip when shuffle option. Now add the Podcasts to your iPod's playlist, right-click and select Add to Playlist and then select the Playlist of your iPod shuffle. After the shuffle updates and you disconnect you can revert the shuffle option back to no (if not they will play when you have it set to random in iTunes) or just delete the podcast altogether.
I hope this helps someone that might have the same problem I ran into.