iTunes 7 sync problems and large libraries on external drives

Update: This problem seems to have been addressed in a recent update to iTunes. The program now stops looking around 100 missing files before giving the warning dialogue. So if you’re having this problem, make sure you’re using the latest version.

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One of iTunes 7 handy new features is the “sync problems” warning. The screen pops up whenever you try to sync your iPod with your iTunes library and song/video/podcast files cannot be found. Previous versions of iTunes only let you know there was a problem; iTunes 7, however, helpfully tells you which particular files are missing.

It’s a nifty function for tracking down errant files that iTunes has somehow lost or forgotten about. or which you may have accidently deleted. But that helpfulness can cause problems in certain instances.

You see, I have a rather large iTunes library: 14,000+ songs that take up ~78GB of hard disk space. So I keep all my song files on a dedicated external hard drive, a hard drive that isn’t always turned on.

In previous versions of iTunes, if song files could not be found when attempting to sync your iPod, you would just get a warning about a single missing file, but all your recent play stats (play count, star ratings, last played) would still be updated from the iPod into the main iTunes library.

However, when doing the same thing in iTunes 7, the program begins to compile its detailed report. In my case, if the external library is not mounted on the desktop and i try to sync my iPod, iTunes then starts trying to find all 14,000+ missing song files.

The program seemingly freezes (the dreaded beachball) while it is processing all those missing files. The only options are to wait for it to finish (which takes more than an hour on my Intel iMac) or force quit (and lose any stored play count and last played data from the iPod). I found this out the hard way, twice, before I realized what was going on.

So, just a quick word of advice: if you’ve got an external library, make sure it is powered on and mounted before opening iTunes.

Migrate Your iTunes Library from Windows to Mac (and keep your ratings, play counts and date added)

Note: This article was written with iTunes 7 in mind. However, the principle holds for moving comparable versions (ie iTunes 6 Win to iTunes 6 mac) or for moving upstream (iTunes 6 to iTunes 7). Also, the procedure should work for moving your iTunes library from one computer to another, Mac-to-Mac, PC-to-PC, or any combination of the two. You can even use this method to clone an iTunes library from one computer to many others.

windows iTunes migration
Apple’s market share has been growing dramatically. Many observers attribute that growth to the introduction of the Intel-based Macintosh as well as the so-called “halo effect” of the iTunes-iPod phenomenon. If you’re one of those users who have made the switch from Windows to Mac OS X because of said halo then you probably have already established an iTunes Library (with valuable hours spent creating playlists, rating songs and increasing play counts).

It would be a shame to lose all that hard work and data when switching platforms. Fortunately, it is a rather simple* procedure to move all your music to your new Mac while preserving all that precious, gooey metadata. Some guides say to export your existing library to XML and re-import it one the new machine. But that’s a bit complicated and it doesn’t really work. Since both the Mac and Windows versions of iTunes use the same file format for the library file, all you need to do is copy the library files from one computer to the other, while making sure iTunes doesn’t forget where the songs are located.

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Happy Birthday iPod

Well, today is the 5th birthday of the iPod. Hooray! Time to pack the little guy a lunch and send him to kindergarten. Seems like only yesterday he was a mere 5 gigabytes tall. Now look at him: about 80!

And he’s much more talented now. I remember being smilingly proud the day he shuffled his first playlist, lo those years ago. And now he’s out there playing games and showing off his pictures and movies to people and making new friends everyday. Brings a tear to my eye.

Yep. iPod is all grow’d up. Happy Birthday iPod.

Flickr, Bootlegs, Live Recordings and iTunes Album Art


Tortoise at the Independent
Originally uploaded by Luiza.

Whereas my previous iPod, a 3rd generation model, could not display album art, my new one, of course can. So I spent a portion of my morning going through my library, searching for albums that were missing their covers. During the process, I ran into a couple live shows that, since they aren’t formally-released albums, obviously don’t have album covers.

Specifically, I had a Tortoise show in San Francisco from October 2005 and a Mouse on Mars show in Toronto from October 2004.

Most music clubs I’ve been to in recent years seem to have a laid-back “we-don’t-care” policy toward shooting photos of the acts that roll through, so it is not uncommon to see folks with digital cameras snapping away. Heck, I even saw someone with a video camera (or possibly 8mm) at a recent Ratatat show.

Even if a venue does prohibit recordings and photography, the rise of cell phone cameras and pocket point-and-shoots almost ensures that some clandestine pictures will escape.

Knowing this, I went over to Flickr, where a good portion of the world’s digital pictures eventually end up. I hoped to find, if not pics from the specific shows, something close enough for displaying on my iPod.

The mission was a success. A couple searches later, I found a really nice shot from the exact Tortoise show at The Independent shown above. I did not, however, track down anything from Mouse on Mars’ performance at Lee’s Palace. But I did get a nice one from the show in Montreal the day before and that’s close enough for rock and roll.

Those two shows now have some nice iTunes artwork.

Viva Flickr.

Compilations, Coverflow, Art and Album Artist

coverflow compilations iTunes 7

Dilemma: When using coverflow view in iTunes 7, your albums containing multiple artists (soundtracks, tribute albums, benefit albums, etc) show up with multiple, individual covers. One way to fix that is to set the Compilation tag check box for those albums. But what if, for whatever reason, you don’t want to set an album as a compilation? (They’re your reasons; I won’t question them. For instance, you may not want compilations shunted off into their own little corner of your library.)

An alternate way to bring those multiple covers together provides a worthwhile use to the new and somewhat baffling Album Artist tag. Just put the album/compilation name in Album Artist field and watch as those album covers disappear and consolidate into one.

album artist coverflow field

Ta Da!

iTunes coverflow album artist single

How to use iTunes 7 built-in back up

Another new feature of the newly-minted iTunes 7 is that the program now features a built-in back up system, similar to that originally found in iPhoto. The function allows you to copy either your entire library or just your iTunes Store purchases. However, you are limited to backing up to either CD or DVD, no external drives and no networks.

Select "Back up to disc…" from the file menu.

iTunes 7 backup menu

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