Q: When is a playlist not a playlist?

A: When it won’t play.

I have an iPod Nano, 2nd generation. I have a pretty simple routine for using it. I have two smart playlists in iTunes that I sync with the Nano, one contains music, and one contains podcasts. Every week, I update the podcasts, randomize the music, and sync my iPod. I always leave my iPod set to “shuffle songs”. Whether I am listening to music or podcasts, I want to pick the next one randomly. I don’t want to listen in alphabetic order. I listen to my iPod primarily in the car, and mostly listen to podcasts as opposed to music. I typically have several episodes of each podcast in the playlist. While driving, when one podcast ends, I don’t want to fiddle with my iPod, I just want it to start playing the next podcast. I also don’t want to listen to all the episodes of a single podcast before hearing any of the others. (Who could stand 4 episodes of Car Talk in a row?) None of the available sort orders in iTunes seems right. Date Modified seemed like a good choice, but some providers modify a lot of their podcasts at the same time, so I would get, say, a bunch of NPR podcasts in a row. So the best for me is random, aka shuffle. If I do hear the same one twice, or something I don’t like, all I have to do is hit the next button on the iPod to skip past it.

Way back in 2006, this stopped working for me when I upgraded from firmware 1.1.1 to 1.2. As I understood the situation then, in iPod Nano firmware 1.2:

1.) Any playlist with only podcasts won’t play.

2.) A playlist with some songs and some podcasts will play, but only the songs will play. A playlist with 2 songs and 10 podcasts plays, saying “1 of 2″.

There was some discussion about this on the Apple support forums, but no real resolution, except to revert to 1.1.1. Surely, I thought, Apple would fix this egregious bug in later firmware versions. However, Apple never says what changes are made in any of the iPod firmware releases, so I just stayed with 1.1.1.

When iTunes 9.0.2 came out, it was incompatible with the old firmware and all of a sudden, I couldn’t connect my iPod to iTunes anymore. I was forced to update the firmware to 1.3.1 (BTW, this was way, way too difficult), and the problem was back.

Finally, after four years, I understand what the problem was. It’s not a bug, it’s a “feature”. Podcasts typically all have an obscure setting called Skip when shuffling turned on. Since I always had Shuffle Songs turned on, I could never play any podcasts as part of a playlist. The only way to play a podcast was one at a time. I now understand that firmware 1.1.1 was the last release for the Nano that didn’t implement the Skip when shuffling bit. It sure would have been nice if Apple had been telling us what changed in each firmware release.

Somebody at Apple decided, in their infinite wisdom, that nobody would ever want to shuffle podcasts. Well, hello, I do! I can understand that you might not want certain tracks to play in rotation, but when they are chosen by the user to be in a playlist, the user has spoken, and his choice should be honored.

There are a couple of things Apple could do about this. The best would be to fix iPod firmware to ignore Skip when shuffling when playing a playlist, but honor it when the user is playing everything on the iPod in shuffle mode. Another way would be an option in iTunes to clear the Skip when shuffling bit when downloading podcasts, or when creating a playlist.

Meanwhile there is a work-around. When you have your podcasts downloaded, before syncing them to the iPod, Select All in the playlist, Get Info, and click the options tab, and then select no for Skip when shuffling. When you apply this, it will get rid of the pesky Skip when shuffling bit on all tracks in the playlist.

This is a poor workaround, since the Skip when shuffling attribute is removed from those files, not just within the playlist, but in your entire library, and all devices syncing with your library. I approve of the designed behavior of Skip when shuffling in general, but it should not apply inside a playlist.

Does anyone know if this problem is the same on other iPod versions?

-Jamie Cox

On looking at the duplicate entries they are apparently identical. Why oh why can’t Apple’s iSync be smart enough to recognize these automatically?

Right now, I’m trying to clean up my address book which now has hundreds of contacts which have 2, 3 or even 4 duplicate entries. That’s a lot of work that I shouldn’t have to do. This stuff should just *work*. This is not rocket science.

I’m currently on the newest version of MacOS, Snow Leopard, MacOS 10.6.2, but as far as I can tell, nothing has improved on this front in many versions.

When syncing, it will also randomly pick some items that are in “conflict”. When you click Details, it asks which version of the contact you would like to save. However, in a horrible user-interface bug, it usually fails to show any of the contact details which would allow you to make an intelligent choice! You just get “John Doe, .Mac”, “John Doe, Address Book”, pick one. How do I know which one is right? It doesn’t show the phone number, email address or anything else! UI Fail.

I can’t be the only one. Anyone else have these problems too?

-Jamie Cox

P.S. It *is* nice that Apple added sync with Google contacts as an option, but it doesn’t work any better than the other options.