Troubleshooting iTunes

Note: this article is taken from iLife '05: The Missing Manual By David Pogue
ISBN: 0-596-10036-1 Copyright 2005 David Pogue. All rights reserved.
Used with permission from the publisher. Available from booksellers or direct from O'Reilly Media, www.oreilly.com.

When you get right down to it, iTunes is a glorified database. It's a list-a searchable, sortable list-but a very high-profile one with some stiff competition (at least in the Windows world, where iTunes is also popular). For these reasons, Apple has put a lot of effort into making iTunes rock-solid. Not a lot goes wrong in iTunes.

But when the planets don't align your way, may this chapter be your guide to iTunes wholeness.

Rule 1: Get the Latest

Upgrading to iTunes 4.9 or later is the most important step you can take. It cures a long list of glitches that were possible in earlier versions. For example:

  • You can't listen to someone else's shared music over the network if they have a big music library. (The "Loading" message appears, but the shared library never does appear.)

  • iTunes suddenly crashes when you try to listen to certain radio stations (those whose Web addresses don't begin with http://).

  • You try to share music with a version of iTunes before 4.5 (and get a "not compatible with this version of iTunes" message).

In these cases and many others, just downloading the free update to iTunes 4.9 or later solves the problem.

Rule 2: Back Up Your Library

Having a backup of your music files is excellent insurance against all sorts of music-library corruption. It's also a safety net for all the music you've bought from the iTunes Music Store; if something goes wrong with your hard drive, and you don't have a backup, you have to buy all of it again.

Backing Up to a Hard Drive or Another Mac

If you've got an external hard drive (the hard drive in another Mac on the network counts), backing up your music collection is extremely easy. Open your Home → Music folder, and copy the iTunes folder inside it. That's it-you're backed up. (In the event of catastrophe, simply restore this backup copy to its original location.)

Backing Up to CD or DVD

You can copy about 650 megabytes of music files to a recordable CD, or (if your Mac has a DVD burner) about 4.7 gigabytes to a blank DVD.

Start by creating a playlist of your entire music library, like this:

  1. In iTunes, click Library in the Source list.
    Make sure that the Search box is empty-that you're viewing your entire list of songs.

  2. Click a song, and then choose Edit → Select All.
    iTunes highlights all of your songs.

  3. Choose File → New Playlist From Selection.
    iTunes asks you to name the new playlist.

  4. Type Full Backup (or whatever name you like).
    Now you're ready to create the backup disc.

  5. Choose iTunes → Preferences; in the Preferences dialog box, click Burning. Click "Data CD or DVD," and click OK.
    You're going to burn a computer disc, that is, not one intended for playing in stereos.

  6. Select the playlist you created in step 4, and then click the Burn Disc button. Insert a blank CD or DVD (either an -R or -RW blank format), and click Burn Disc again.
    iTunes backs up all your audio files. If you need more than one disc to hold it all, iTunes will let you know, and invite you to insert a second disc.


You don't have to back up your entire music library each time. Thanks to the magic of the Smart Playlist, you can back up only the newest arrivals on successive backups.

To do that, note the date and time of the first complete backup. Then just create a new Smart Playlist that includes all songs with whose Date Added is after that. When you want to back up that newest batch, just repeat the steps above-but click your Smart Playlist's name in step 6.

Each time you perform one of these so-called incremental backups, remember to click the Smart Playlist, choose Edit → Edit Smart Playlist, and change the date to today's date. You've just reset the Smart Playlist so that it will begin collecting new new songs.

Store-Bought Songs Won't Play

If you can't play songs you've bought online, the problem almost always boils down to one of these three things:

  • You don't have QuickTime 6.2.5 or later.
    You need at least this version of Apple's QuickTime music-and-movie-playing software if you hope to use your store-bought songs in the other iLife programs, like using a song as a background in an iMovie movie.

    To find out what version you have, open System Preferences, click QuickTime, and click the About QuickTime button. If it turns out you don't have the latest version of QuickTime, stay right there in System Preferences. Choose View → Software Update, click Update Software, make sure you can get online, and then click Check Now. After a moment, you'll be offered the opportunity to download the latest, greatest version of QuickTime.

    QuickTime Player vs. QuickTime Player Pro

    OK, I tried to update my copy of QuickTime like you said. But the updater asks me for my name, company, and a "QuickTime Pro key!" What the heck is that?

    QuickTime Pro is a $30 upgrade (to the free QuickTime you just downloaded). It adds the ability to edit QuickTime movies (instead of just watching them), among other goodies.

    If you had paid for this upgrade, this would be your opportunity to plug in the serial number you were sent by email. But if you have no intention of upgrading to Pro, just leave the boxes blank and click Continue. Unlike other programs that sit down and refuse to cooperate if you don't have a serial number, QuickTime lets you play for free.

  • Your permissions are scrambled.
    An amazing number of mysterious glitches arise because the permissions of either that item or something in your System folder have become muddled-that is, Mac OS X's complex mesh of interconnected Unix permissions settings. Music-store songs not playing back is among them.

    In that case, open your Applications → Utilities folder and open Disk Utility.

    Then proceed as shown in Figure30-1.

Figure 30-1. Click your hard drive's name in the left-side list; click the First Aid tab; click Repair Disk Permissions; and then read an article while the Mac checks out your disk. If the program finds anything amiss, you'll see messages like these.

  • You've authorized too many computers.
    Remember, once you buy a song online, you're allowed to play it on a maximum of five computers (Macs or PCs).

    Rack your brain: Is it possible you authorized somebody's Mac so they could hear something you bought, forgot to de-authorize it, and now you're over the limit?

    Anyway, you remove a computer from your designated set by choosing Advanced → Deauthorize Computer while you're online. In the resulting dialog box, choose "Deauthorize Computer for Apple Account" and then click OK. If you've already given the computer away, check out the tip on Section 4.4.4 for a quick fix.

  • You can't listen to store-bought songs across the network.
    If you, seated at Computer A, are trying to listen to the music on Computer B using the playlist-sharing feature described on Section 2.6, you may notice that iTunes skips over any songs that came from the iTunes Music Store. That, alas, is normal behavior. Unless you make Computer A one of the five authorized machines for your account, you won't be able to hear Computer B's store-bought tunes.

Playback Problems

Playing back music is a pretty essential and simple task: Just tap the Space bar. Troubleshooting playback is pretty simple, too:

The Music Is Too Quiet
Remember that you're now contending with two different volume levels: your Mac's own speaker volume (which you can adjust with the volume keys on your keyboard, or using the Sound panel of System Preferences) and the little volume slider at the top of the iTunes window. Adjust both of them.

If you can't hear anything at all, make sure that you don't have external speakers or headphones plugged into your Mac (which cuts off all sound to the built-in speaker).

And if you have an AirPort Express wireless networking base station, make sure that the pop-up menu at the bottom edge of the iTunes window is set correctly. If you're trying to play back the music using your Mac's built-in speakers, make sure this pop-up menu says Computer. And if you're attempting to direct playback to whatever speakers are attached to the AirPort Express, make sure they're turned on and hooked up right.

The Songs Overlap Each Other
It's a feature, not a bug. Choose iTunes → Preferences, click Audio, and turn off Crossfade Playback.

Files Missing in Action

Every once in while iTunes throws you a curveball out of the blue that can range from minorly annoying to downright panic-inducing. Here are a few common issues to look out for:

My Podcast Didn't Get Updated
Keeping current with the latest episode of your favorite podcast is easy with iTunes, since the program does most of the work of checking for-and downloading-fresh installments. If one of your regular shows doesn't get updated, though, the server that actually hosts the program may be down or busy, and iTunes itself can't get through to grab the new installment. In iTunes, click the Update button in the upper right corner of the Podcasts playlist to reach out for the show manually. Or try waiting a while before trying again, in case the server is still having a really, really bad day.

I Get a "Movie File Cannot Be Found" Error
You can play .mov and .mp4 movies right in iTunes 4.8 and later, but the program sometimes gets discombobulated if you have QuickTime "reference movies" in the mix. These reference movies are typically temporary pointer files that aimed at the location of the real movie in whatever program it was created in, but they can confuse iTunes when you try to play them.

To fix the error, choose Edit → View Options, check the box next to Kind and click OK. Click Library in the iTunes Source list, then click the new Kind column header you just made to sort your collection by file type. Scroll down to the QuickTime movie file section and double-click each file to make sure it plays. If you get the error messgage, click the Cancel button in the box, select the offending file, and choose Edit → Clear to boot the bad seed off the list.

I Upgraded iTunes and All My Music Is Gone!
Sure, you think you're doing the right thing by upgrading, but sometimes things can go wacky when you install a new version of iTunes. If you update the program and start it up to find out that your entire libary has vanished, take a deep breath, put down the sharp object, and quit out of the iTunes program for a minute.

Just remember that your music is still on the Mac, but this new version of iTunes doesn't know where to look for it.

Now then, go find the folder that iTunes stores your music library's database file. Unless you've fiddled with the default settings, it's in your Home → Music → iTunes folder. Drag the file in there called iTunes Library out of the folder and dump it onto your desktop.

Next, go back to that main iTunes folder and open the subfolder called Previous iTunes Libraries that's tucked inside. Find the file called iTunes 4 Music Library in there and drag that out into the main iTunes folder where the old one used to be.

Restart iTunes. You should see all your old music, right where you left it.


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