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Apple has created a winning combination with iTunes and the iPod—products that are both fun and easy to use. But even these well-designed feats of Apple software and hardware engineering can cause a few headaches from time to time (some of the new difficulties are due to changes wrought by Tiger). Here are some problems you’re likely to encounter and how to fix them.

Sync contacts and calendars

I used to use iSync to sync my Mac’s Address Book contacts and iCal calendars with my iPod. Now that I’ve switched to Tiger, my iPod no longer shows up in iSync.

With Tiger, Apple removed syncing for iPods (but not for PDAs and cell phones) from its iSync 2.0 synchronization application and moved that functionality into iTunes. To activate synchronization of calendars and contacts with your iPod, first go to iTunes’ iPod preference pane. There you’ll find both Contacts and Calendars tabs. Within each, you can choose to enable synchronization, as well as whether to sync all contacts or calendars or just selected groups or calendars (see top screenshot). The big benefit to moving these functions into iTunes is that the information will automatically update whenever you plug in your iPod—you no longer need to remember to launch iSync and click on the Sync Devices button.

Access your protected music files

After I upgraded to Tiger, songs I had purchased from the iTunes Music Store stopped syncing with my iPod and no longer played in iTunes.

For some reason, upgrading to Tiger confuses many Macs when it comes to iTunes Music Store content. I’ve witnessed people connecting their iPods after an upgrade to Tiger, only to find that their purchased music wouldn’t sync as it had before. And the first time I launched iTunes after upgrading, I could select a purchased song in iTunes, but when I attempted to play it on the Mac, nothing happened. If you’re having this problem, the solution is simple: select Deauthorize Computer from iTunes’ Advanced menu, and then double-click on one of your protected purchased music files. iTunes will prompt you to enter your password, and it will then connect to a server to reestablish your ability to play and transfer those files (don’t worry, iTunes won’t interpret this procedure as adding another authorized computer).

Reset your authorized Macs

When I try to authorize a Mac to play my purchased music, iTunes claims I’ve reached my limit.

If you’ve authorized five computers to listen to songs you’ve purchased from the iTunes Music Store, then you’ve reached Apple’s limit. To listen on another computer, you’ll need to deauthorize one (in iTunes, choose Advanced: Deauthorize Computer). But what if you’ve swapped hard drives or sold an old Mac, or what if you just don’t have access to one of the computers you want to deauthorize?

Select Music Store in iTunes’ Source window, and then log in to your iTunes account by clicking on your name next to the word Account in the upper right corner, entering your password, and clicking on the View Account button. If you’ve used up all your authorizations, you’ll see a line that reads “Computer Authorizations: 5 machines are authorized to play music purchased with this account.” Click on the Deauthorize All button, and Apple will clear its database of all Macs authorized to play songs linked to your account—including machines with dead hard drives, those you’ve given away, and so on (note that this button appears only when you’ve used up all five of your authorizations). The next time you try to listen to your purchased music on any Mac, iTunes will prompt you to enter your password and authorize that computer.

Display artwork for current songs

When iTunes switches to a new song, the album art doesn’t change along with it.

By default, iTunes shows you the album art for the track you’ve selected and highlighted—that way, you don’t have to play a song to see the art associated with it. If you’d prefer to see the cover for the song you’re listening to at any given moment, click on the album-art window’s title bar (see bottom screenshot) to toggle it from Selected Song to Now Playing.

Exclude certain songs from shuffle

When shuffling through the music in my library, I don’t really want to hear comedy routines or my voice recordings—but iTunes doesn’t differentiate between those and music.

You could create a smart playlist, but another way is to use iTunes’ check boxes. iTunes picks only songs with check marks to the left of their names, so you can just deselect the songs you want excluded—they’ll still play if you select them manually. If you have lots of songs to exclude, create a playlist with all the songs in it, and then select all of them and control-click on one of the tracks. iTunes will give you an Uncheck Selection option—much easier than clicking on check boxes one at a time. l

[ Senior News Editor Jonathan Seff alternates between a 40GB fourth-generation iPod and a 512MB iPod shuffle, and his iTunes library is approaching 19,000 songs. ]

With iTunes taking over duties from iSync, getting your contacts and calendars onto your iPod is easier than ever.Sick of not seeing the correct artwork for the current song? Change the album-art window’s title bar to Now Playing.
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