The first and probably only thing you will find while searching the Internet for iTunes-to-Android products is DoubleTwist. Frankly, I hate it. It tries to do too much. It wants to replace iTunes, but is clearly not up to that task. Every time I start it, it treats my 1 TB USB external hard drive like a device that needs to be synchronized. There is no way to dissuade it from this behavior.

DoubleTwist will import playlists from iTunes and sync them to an Android device. This is the behavior I wanted from the program, but there were too many problems.

It is glacially slow. Worst of all, DoubleTwist failed to actually synchronize my files more often than it succeeded. Usually it would say it was done, but the transfer was very incomplete, or the old playlists were still there. Support at DoubleTwist answered my request for help, and suggested deleting DoubleTwist’s preferences files and retrying. This worked once, and then the program went back to its old ways.

Enter Salling Media Sync. When you connect an Android device, Salling Media Sync brings up a very iTunes-like interface to let you choose playlists, photos, etc., to be synchronized to your Android. That’s all it does, but it’s worked every time, and that’s all I wanted it to do.

On the downside, Salling Media Sync doesn’t act like a proper Mac application. It installs itself in the menu bar. I really don’t need anything else in my menu bar, thanks. The application has windows, but no menu bar of its own. Apparently, it runs all the time. There’s no way to quit it. I really only need it about once a week.

DoubleTwist is free.
Salling Media Sync is also free. A registered version makes sync go faster. The unregistered version replaces all files at each sync. The registered version intelligently only replaces those that need to be replaced. Registration is $22. The unregistered version updates my ~ 3GB playlists in about 40 minutes. This is mostly related to the speed of the flash memory card in my phone, I think. As I understand it, if you have a lot of turnover in what you are syncing, registration won’t make much difference. But, if you mostly keep the same file content from sync to sync, then the registration will make it go much faster.

-Jamie

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