I recently posted about a trick in iTunes to fix an issue where the sort order chosen for a playlist in iTunes doesn’t get copied over to the iPod unless you right click on the playlist in iTunes and choose “Copy to Sort Order” before syncing.

In a strange twist of fate this trick stopped working for the Smart Playlist I use to listen to Podcasts on my iPod Touch within days of posting the tutorial. It seems that a new bug appeared in either the iPod OS 3.1.x, or perhaps in iTunes itself, and so far there is no official fix.

The issue is that certain combinations of settings for Smart Playlists result in the sort order selected in iTunes not being synced onto the iPod, regardless of whether “Copy to Sort Order” is selected. Note that the sort order appears to transfer if you look at the iPod version of the playlist within iTunes, but not when you look on the iPod itself.

There are various combinations of settings for the Smart Playlist that will resolve this problem (including turning off “Live Updating”, but that defeats the purpose of using a Smart Playlist for Podcasts in the first place), and certainly multiple combinations for which the error occurs. I haven’t even begun to look for all of them, but I have found one that works very well and gets my Podcast Playlist working perfectly.

If you want iTunes to be able to update your Smart Playlist for Podcasts correctly with the sort order you selected in iTunes, try setting up your playlist as follows:

1. Checked: Match ALL of the following rules:
2. Playlist IS NOT Music
3. Media Kind IS Podcast
4. Checked: Match only checked items
5. Checked: Live updating

Most likely the only change is the addition of item 2 above. The other settings are all defaults for Smart Playlists and will only be different if you intentionally changed them for some reason.

NOTE – You will still have to use the “Copy to Sort Order” trick I previously posted (because that’s how iTunes was designed). Today’s fix merely gets you back to the point where that trick actually works…

I have submitted this as a bug to Apple, but similar bugs have existed for ages so I’m not holding my breath that they’re going to fix this one anytime soon.

I listen to lots of Podcasts on my iPod Touch and I prefer to listen to them in the order that they are released. Podcasts are much like radio or TV shows in that the information presented is often timely, or at least referential to prior episodes, and so it generally makes more sense to listen to shows in the order they are released so that related and timely information is heard around about the same time.

The included “Podcasts” view in iTunes and on my iPod Touch groups different episodes of the same show together with no option to see all episodes of all shows in one big list. This makes it easy to listen to all the episodes of one show in the order they were released, but virtually impossible to listen to all episodes of all shows in the order they were released.

I got around that by creating a Smart Playlist that searches my iTunes Library for Podcasts. My preferred sort order for that playlist, naturally, is by date. That sort order gets transferred over to the iPod initially, and as new shows are added (as they automatically get downloaded by iTunes) they get added to the end of the list in the order they are downloaded. This works extremely well for me most of the time.

Unfortunately every once in awhile the sort order on my iPod gets out of whack (seemingly at random, and in a totally random order), and there is no way on the iPod to reorganize playlists. /They can be reorganized in many different ways in iTunes (by artist, by date, alphabetically, etc.), but I couldn’t figure out how to sync those changes back to my iPod. No matter what I changed in iTunes, the sort order on my iPod stayed scrambled.

Finally I noticed a cryptic command on the right-click menu for the playlist called “Copy to Play Order“. I still have no idea what the name of this command is supposed to mean, because it doesn’t do anything to the playlist in iTunes, but after choosing this option and syncing the iPod to iTunes, the sort order for my playlist magically matches with that in iTunes. Yay!

I don’t understand why I would have to take this extra step as it seems obvious to me that if I can’t sort my playlists directly on the iPod, but I can in iTunes, then I probably want the sort order on my iPod to match what I choose in iTunes. Is that so much of a stretch??