I'm desperate to find out. If there is not a way, I've got to hack it. I run 5 miles a day and have to fumble around and go through a series of annoying commands every single time a podcast ends, several times during my run. Also while driving this is not safe. Newest iPod nano: How can I play all my Podcasts at once without having to re-hit the play button after every single podcast? Shuffle is OFF. This is supposed to fix it but does not. My op system is OSX 10.4.11, and I have all of the latest iTunes updates and Mac updates installed. Thanks!