Blog: A cautionary tale for iTunes users

Every couple of years, iTunes blows up on me and I really hate Apple for a week or so. Once upon a time, I was a huge Apple booster, buying only Macs, writing for user groups and even editing an e-zine devoted to MacDoom fans. But these days my biggest connection to Cupertino is my iPod.

When you start out, the iPod is super easy to use and a good quality audio device; it almost justifies its high end pricing. But once you invest time and money to build up a huge library of music, things get hairy. About every two years, the files I've collected outgrow my hard drive and need to be moved. The first time, I just drag copied the files. I figured everything else was so easy with iTunes, why shouldn't this be? Surely, the metadata (song ratings, etc.) are embedded with the music files, and the playlists are standalone files like with Windows Media Player.

Alas, no - as I learned the hard way. iTunes stores this data in XML and database files, so you need to let iTunes do the moving for you. Back then, I had all of my music files backed up on my iPod (when they still all fit), so I was able to buy a third-party extractor to pull them back off onto my hard drive, preserving my ratings and playlists.

It's also worth pointing out that, unlike some online stores, you can only download a file once - so you'd better back up any music, videos or games you pay for (as well as their weekly freebies). I think it cost me about $20 to fix that nearly fatal error.

Flash forward to last week. I found some handy tutorials that walked me through the supposedly foolproof music migration process. You simply let iTunes manage your files, select a new location for your files within the program's settings, and then tell the player to Consolidate Library.

First off, let me recommend that you BACK UP everything before trying this. All of your music files, plus your database files (which tend to remain in your My Music folder on your default hard drive - aka "C:\:" on a Windows PC - along with any games you purchased). This will make restoring everything much simpler if things go horribly wrong. As they did for me.

The consolidation process took several hours. When it was through, only about 75 percent of my 16,000 files actually moved. My fatal error this time, it seems, is that the drive I chose was a Western Digital MyBook connected via USB to a remote D-Link network hard drive. Apparently, network drives are not usable by iTunes since it detects a lag and then marks the files as Streaming, which then makes them unplayable. (Hey, Apple, why don't you sniff for latency and warn us before trying to copy our files to a drive that's not fast enough for your software?! And let us toggle files from Stream back to standard play.)

But even that should be no problem, right? I'll just hook the hard drive directly to my PC, make sure it has the same drive letter and I'm golden, right? Alas, the MyBook doesn't get along with my Windows XP SP2 machine. Every time I try to copy a file to the MyBook when it's directly connected via USB, I instantly get a blue screen of death. Even in Safe Mode. (And, yes, I have all of the latest Microsoft system patches.)

Next I tried to manually edit the Library XML file to point back to my old drive (where I had not deleted the original files, thankfully). After searching and replacing some 10,000 entries with PSPad, I found that this data is duplicated in another, non-editable database file. So whenever I relaunch iTunes, it changes all of the paths back to the bad drive. Gee, thanks.

So far, the only solution I have found is to manually reconnect each file on the old drive to iTunes. This means deleting the file on the remote drive, clicking the entry in iTunes, and then browsing to the same file on the old drive. With about 10,000 files that need repointing, it will take me at least a month (assuming I can repoint about 350 each day) and possibly through the end of the year (if I only average 100 per day).

This still doesn't solve my original space problem. When I'm done, I'll be back to using the same drive that is full up and may fail on me sooner than the newer MyBook. So I plan to move some files into cold storage (leaving them marked as missing for now) and eventually migrate them to a locally connected drive that does not crash whenever I copy files to it. I'll also tell iTunes that it no longer gets to manage my files, since I don't want them consolidated on the same drive anymore.

If anyone knows a better fix for this, please let me know. And if you're thinking of moving your own iTunes library, take precautions if you don't want to join me in my new daily routine: Right-click, Ctrl-A, delete, select path, Ctrl-C, Alt-Tab, click, click, double-click, click, Ctrl-V, enter, double-click, repeat.

Right now, I'm up to the B's.

-=Gamewatcher