I’ve had a long-standing issue with my iPod Shuffle (first gen) where regardless of what order I place my music and podcasts in, podcasts always play before music, and the podcasts play in reverse chronological order (so newest podcast first). I had read of a solution in which deleting your iTunes Database and other files would fix the problem, but I have so many custom playlists related to podcasts that it seemed like less work to deal with the weird sort order than to try to recreate my iTunes environment.

This was all peachy until a few months ago. I abused my 512MB shuffle so much that the headset jack was loose and it would only play audio through one channel. I really wanted another 1st-gen Shuffle (the built-in USB jack is the killer feature for me) and I eventually found out that my niece had upgraded to a nano. After some not-especially-fierce haggling I bought her 1st-gen 1GB Shuffle. Both audio channels, more storage, and as an added bonus, a sane playlist order!

That’s right, somehow her iPod allowed me to sort the podcasts in the order I wanted them to be in. Heaven.

Then a week ago, to fix some perceived problem, I updated the iPod software to 1.1.5 (I don’t know what version it had on it before – based on the rest of this story it seems likely it had an older release, but it seems unlike me not to immediately update the software). Guess what? Podcasts went back to the old behavior where they were played in reverse chronological order. Hell.

I finally got mad enough to spend some time on the problem. One very valuable piece of information I had this time is that there was nothing necessarily tying my problem to my specific machine, since I had used this newer shuffle for a few months on this PC without problems.

The first thing I tried was reformatting the iPod on my Mac Server. Didn’t work. Then I tried moving my iTunes folder out of the way and reinstalling. Didn’t work. Drat. That was basically the suggestion of people to rebuild your iTunes library.

One very interesting thing I did find is that this behavior isn’t really hard coded to reverse-chronological. It’s actually tied to the sort order of your “Podcasts” Library section. I was able to prove this to myself, I could change to forward chronological and the podcasts would always play oldest to newest. This wasn’t perfect (I really want to listen to “today’s” podcasts in whatever order, then listen to “older” podcasts oldest-to-newest. I like having finer control than that, but that’s all I really need).

I was excited for a few minutes because I though “ah, I don’t need very granular control, I can just create an artificial rating and sort on it!” Nope. I have no idea why (older posts I found indicated this wasn’t always the case) but my iTunes (8.0.2.20 on Windows XP) will only allow me to sort on the “Release Date” column, so my idea of rating the “daily” podcasts 5 stars and the “other” podcasts 3 stars wouldn’t work. Drat.

I finally came full circle and realized that maybe it was a software revision issue. I know my problem started when I installed 1.1.5, but I don’t know what version it had previously been running. Also, I found no mention of software version in the (many) discussions of this issue on the web. In fact, I found several that swore up and down that “nothing had changed”. Sure, right.

I had spent so much time on this that giving up would have left me not only unhappy with the Shuffle behavior but also with all the time I wasted. So, I tried the thing I was sure would fail (and in fact that I wasn’t even sure I would be able to attempt). I downgraded from release 1.1.5 to 1.1.4. Et voila! I can’t believe that worked! How did you not tell me that, Internet? =)

Here are the exact steps I followed that fixed my problem. I think some of them are superfluous (I doubt it matters that I did the actual update on a Mac) but I want to state what I did exactly since there seems to be a lot of confusion on this issue:

• Download iPod Updater 2006-06-28 from Apple
• Install updater on my Mac server (still running 10.3.9, iTunes 7.7.1(11) – don’t laugh, it’s rock solid)
• Quit iTunes
• Delete iTunes folder (after making a backup of course)
• Run iPod updater
• Choose “restore”, say yes to everything
• “Quit” the updater when it informs you that the iPod is restarting
• Once iTunes starts up (it did so automatically for me) and you’ve renamed the iPod, unplug it
• Transfer iPod to Win XP machine running iTunes 8.0.2.20. “Erase” when you are informed that your iPod is attached to another machine
• Transfer a couple podcasts and a couple of songs to the iPod, sort to the two types are intermixed
• unplug shuffle
• plug shuffle back in
• See that the podcasts and songs are in same order as when you unplugged!

Like I said, it probably doesn’t matter that I did it on a different machine or that I delete the iTunes folder while doing it, but those are the steps I happened to do that worked.