iTunes is your iPad’s best friend. You can do just about everything with your digital media here—convert songs on a CD into iPad-ready music files; buy music, movies, and TV shows; add apps; listen to Internet radio stations; and more. Here’s a quick tour of the iTunes window and what all the buttons, controls, and sliders do.

The gray Source panel on the left side of the iTunes window displays all your media libraries—for audio, videos, books, and more.

The outer edges of the iTunes window are full of buttons and controls:

As mentioned earlier, iTunes groups your media into libraries in the Source list. Music, videos, applications, and other content you download from the iTunes Store land in their respective Source list libraries—songs in the Music library, 30 Rock episodes in TV Shows, and so on. That paid-for music and video also lives in the Source panel’s Purchased list, a one-click trip to see where all your spare cash went.

But say you add files that don’t come from the iTunes Store, like videos you download from the Internet Archive (a great source of free public-domain material, including eBooks, old movies, and years’ worth of Grateful Dead live concert recordings; go to www.archive.org). If one of these files ends up in the wrong part of the iTunes library, you can fix it so that it lands in the proper place—movies in Movies, podcasts in Podcasts, and so on. Click the file you want to reassign in the iTunes window and choose File→Get Info (or press Ctrl-I or ⌘-I) to call up the Info box. Click the Options tab and, next to the label “Media Kind,” select the right category from the pop-up menu, and then click OK.

Behind its steely silver-framed window, iTunes has a very precise system for storing your music, movies, and everything else you add. Inside its own iTunes folder on your hard drive (which, unless you moved it, is in Music→iTunes [Home→Music→iTunes]), the program keeps all your files and media information. (If you’re running Windows 7 or Vista, your iTunes folder is at User→<user name>→Music→iTunes, and Windows XP users can find it at My Documents→My Music→iTunes.)

Your iTunes library file, a database that contains the names of all the songs, playlists, videos, and other content you added to iTunes, sits inside the iTunes folder. Be careful not to move or delete this file if you happen to be poking around in the folder. If iTunes can’t find it, it gives a little sigh and creates a new one—one that doesn’t have a record of all your songs and other media goodies.

If you do accidentally delete the library file, your media is still on your computer—even if iTunes doesn’t know it. That’s because it stores all your media in the iTunes Music folder (or Media folder, as explained in the Tip below), which is also inside the main iTunes folder. You may lose your custom playlist if your library file goes missing, but you can always add your media files back to iTunes (File→Add to Library) to recreate your library.

Click the iTunes Store icon in the Source panel and you land in iTunes’ virtual aisles. The Store is jam-packed with digital merchandise, all neatly filed by category across the top of the main window: Music, Movies, Audiobooks, and so on (but not iBooks; Apple’s iBookstore is only available through the iPad’s iBooks app). Click a tab to go to a store section. You can also hover over a tab and click the triangle that appears; a pop-up menu lets you jump to a subcategory within the section (Blues, Pop, and so on for Music, for example).

The main part of the iTunes Store window—that big piece of real estate smack in the center of your browser—highlights iTunes’ latest audio and video releases and specials. Free song downloads and other offers appear here, too. This window is usually stuffed full of digital goodies, so scroll down the page to see featured movies, TV shows, apps, and freebies.

If you’re looking for a specific item, use the search box in the upper-right corner to hunt your quarry; enter titles, artist names, or other searchable info.

Preview songs by double-clicking the track’s title. The Buy button is there waiting for your impulse purchase, making it extremely easy to run up your credit-card tab.

If your iPad is in range of a wireless or 3G network connection, you have a third way to get to the Store: over the airwaves, as explained on the next page.

If you have an iPad, you don’t even need your stodgy old computer to shop the iTunes Store—you can tap your way right into it over a wireless Internet or 3G connection. Many WiFi–enabled Starbucks coffee shops also let you browse and buy in the iTunes Store, including whatever music is currently playing right there at Starbucks.

Now, to buy stuff when you’re out and about—and in the mood to shop:

Tap the Purchased icon on the iTunes screen to see all the music you’ve ever bought through your iTunes account-and re-download the songs to your iPad.

To get these fresh iPad-bought songs or videos back into your iTunes library (which, of course, sits on your computer), sync up your iPad when you get home. The tracks appear in a new playlist called “Purchased on PadMan” (or whatever you called your tablet this week).

It’s bound to happen sometime: You’re breathlessly downloading a hot new book or movie and your computer freezes, crashes, or your Internet connection goes on the fritz. Or you and your Wi-Fi iPad were in the middle of snagging an album from the wireless iTunes Store, and the rest of the gang decided it was time to leave the coffee shop.

If this happens, don’t worry. Even if your computer crashes or you get knocked offline while you’re downloading a purchase, iTunes is designed to pick up where it left off. Just restart the program and reconnect to the Internet.

If, for some reason, iTunes doesn’t go back to whatever it was downloading before The Incident, choose Store→Check for Available Downloads to resume your downloading business.

You can also check for available purchases any time you think you might have something waiting, like a new episode from a TV Show Season Pass.

Apple’s usage agreement lets you play Store purchases on up to five computers: PCs, Macs, or any combination thereof. Although iTunes Plus songs (those with liner notes and other extras) and songs sold after April 2009 don’t have password-demanding copy restrictions, music tracks purchased before 2009 and most videos still do.

For protected content, you must type in your Apple user name and password on each computer to authorize it to play any songs, videos, or audiobooks purchased with that account. Each computer must have an Internet connection to relay the information back to Store headquarters. (You don’t have to authorize each and every purchase; you just authorize the computer itself.)

You authorized your first machine when you initially signed up for an Apple Account. To authorize another computer, choose Store→Authorize Computer.

You can also share media among the computers on your home network, using the Home Sharing feature built into iTunes 9 and later.

Once you set up all the computers, each of their iTunes libraries appears in everyone else’s Source list. Click the triangle beside the House icon for the library you want to explore. Click on a file to stream it to your own machine over the network. If you must have this file on your computer, select it and click the Import button in the bottom-right corner of the iTunes window. Click the Settings button next to it if you want to automatically copy certain types of files, like Music, among these machines—and your iPad.

Unless you have iTunes Plus tracks, you won’t be able to play copy-protected purchased music, books, or videos on a sixth computer if you try to authorize it. Apple’s authorization system will see five other computers already on its list and deny your request. That’s a drag, but copy protection is copy protection.

To play protected files on Computer Number 6, you have to deauthorize another computer. Choose Store→Deauthorize Computer from the computer about to get the boot, and then type in your Apple Account user name and password. The updated information zips back to Apple.

Are you thinking of putting that older computer up for sale? Before wiping the drive clean and sending it on its way, be sure to deauthorize it, so your new machine will be able to play copy-protected files. Erasing a hard drive, by itself, doesn’t de-authorize the computer.

If you forget to deauthorize a machine before getting rid of it, you can still knock it off your List of Five, but you have to reauthorize every machine in your iTunes arsenal all over again. To make it so, in the iTunes window, click the triangle next to your account name and choose Account. Type in your password. On the account information page where it lists the number of computers you authorized, click the Deauthorize All button (you only see this button if you’ve hit the five-computer limit.) Once you click to deauthorize all your machines, go back to the computers in your Home Sharing network and re-authorize each one.

As with every iPod model that’s come before it, the iPad offers the simple and effective Autosync feature. Autosyncing automatically puts a copy of every song, video, podcast, and other media in your iTunes library right onto your player. In fact, the first time you connect your iPad to your computer, a Setup Assistant offers to copy all the media files in your iTunes library over to your tablet. If you opt to do that, you automatically turn on autosync. (Change your mind later? Never fear. Manually Sync to Your iPad explains how to change sync options.)

If you added more music to iTunes since that first encounter, the steps for loading the new goods onto your iPad couldn’t be easier:

You can tell the sync magic is working because iTunes gives you a progress report at the top of its window that says “Syncing iPad…” (or whatever you’ve named your tablet). When iTunes tells you it’s finished updating your ‘Pad, you’re free to eject it, unplug the cable, and take off.

Autosync is a beautiful thing, but it’s not for everyone—especially if you have more than 16, 32, or 64 gigabytes worth of stuff in your iTunes library. (That may sound like a lot of room for music, but once you start adding hefty video files, that space disappears fast.) If that’s the case, iTunes fits what it can on the iPad.

If autosync isn’t for you, jump over to the next page to read about more selective ways to load up your ‘Pad.

If you opt out of autosyncing your iPad, you now need to go ahead and choose songs or videos for it. Until you do, the iPad just sits there, empty and forlorn in your iTunes window, waiting for you to give it something to play with.

Once your iPad is connected and showing up in iTunes, you can modify all the settings that control what goes onto (and comes off of) your tablet. Thanks to the long, scrollable screen full of checkboxes and lists in most categories, it’s easier than ever to get precisely what you want on your ‘Pad.

If you want to sync up all or just some of your music, click the Music tab.

In addition to synchronizing all your songs and playlists by title, you can sync them by artist and genre as well. Just turn on the checkboxes next to the items you want to transfer to the iPad, click the Apply button, and then click the Sync button to move your music.

Chapter 13 has more on playing music on the iPad.

In iTunes, videos fall into two main classifications—movies and TV shows—and each collection gets its own tab in iTunes. (Podcasts, which can be either audio or video files, stay together in the Podcasts part of the iTunes Library.)

Full-length movies are huge space hogs and can take up a gigabyte or more of precious drive space—which is a significant chunk of a 16-gigabyte iPad. Serious movie-watchers tend to move films on and off space-limited portable devices. So iTunes gives you the option to load all, selected, or even just unwatched films. To change up what’s playing at your portable cineplex, click iTunes’ Movies tab when your iPad’s connected to your computer and turn on the checkboxes next to your cinema selections.

Since the iTunes Store sells TV shows by season or individual episode, iTunes lets you sync TV shows in several ways: by show, by selected episodes, by the number of unwatched episodes, and so on. Click the TV Shows tab with your iPad connected and make your choices.

Once you decide which movies and TV shows you want to port over to the tablet, click the Apply button and then click Sync. Chapter 14 has more on watching video on the iPad.

The iPad, in case you haven’t noticed, makes a handsome electronic picture frame. To get your pictures on it, you can sync photos from your computer’s existing photo-management program, like Adobe Photoshop Elements—or you can copy over a folder of photos. (Chapter 15 has more on displaying photos and making slideshows on the iPad.)

To tell iTunes which pictures you want to take along on your iPad, click the Photos tab. Here, you can select the photo program or folder you want to pull the pictures from, and then turn on checkboxes next to the photos and photo albums you want on the iPad. If you use iPhoto ’09 or later on the Mac, you can pull over iPhoto Events, Faces, and Places, iPhoto’s way of grouping photos by either what’s in them or where you took them. Once you pick your pictures, click Apply and then the Sync button.

As you may remember from Chapter 6, the iPad can carry around a copy of the same personal contact list that you keep on your computer. Even just having the email addresses of everyone you know is handy when you’re catching up on your email in the backyard hammock. Through iTunes, you can grab contacts from a number of popular programs, including Microsoft Outlook 2003 and later, Windows Address Book, Outlook Express, and Windows Contacts. Macs can tap into contact files stored in the Mac OS X Address Book and Entourage 2004 and later. You can also import addresses from Yahoo and Gmail accounts as long as you have an Internet connection.

To copy contacts over to a connected iPad, click the Info tab and use the pop-up menu to choose the program you keep you contacts in. Scroll down the Info screen to see all the other personal data you can sync up:

Make your choices, click the Appy button, and then click Sync to move your life onto the iPad.

One of the coolest features of the iTunes Store is the Podcasts section. Podcasts are like radio and TV shows you can download on a regular basis—for free. Every major media outlet has some sort of audio or video podcast available now alongside more low-budget creations. For example, you can get the video from each week’s edition of Meet the Press from NBC, Slate magazine’s audio critique of released movies, or your favorite shows from National Public Radio.

To sign up for podcasts, click the Podcasts link on the main iTunes Store page and browse until you find something you like. Then click Subscribe.

Once you subscribe to a show, iTunes automatically deposits the latest episode on your computer as soon as it appears online. Since you may not want to fill up your iPad with tons of podcasts, you can tell iTunes which ones to copy over each time you sync up. With the iPad connected, click the Podcasts tab and turn on the checkboxes for the shows you want to sync regularly. Use the pop-up menus to get the number of episodes you want to carry around at any one time, click Apply and then click Sync.

If you’re a big audiobook fan and have been hunting in vain for an Audiobooks tab in iTunes, don’t worry, you’re not missing it. The controls for syncing audiobooks to the iPad are on the Books tab, shoved way down on the screen, where you may have missed it. Scroll down, turn on the checkbox next to Audiobooks (circled), and sync away. You can sync all or selected audiobooks.

You sync text-based eBooks (iBooks and books in the ePub format) the same way, as you can see below. Chapter 8 has all the details on buying and managing eBooks. Note that, in iTunes, you can only back up your iBooks, you can’t buy them or read them on your computer screen. If you have the iBooks app on your iPhone or iPod Touch, you can sync books back to iTunes as well by plugging in those devices and choosing File→Transfer Purchases from iPhone/iPod.

You can also sync PDF files on and off the iPad (see Sync Books with iTunes). Just tap the Collections button in the iBooks app and choose PDFs to see them.

You can listen to audiobooks anywhere, and here’s the cool part: When you sync your iTunes-purchased audiobooks back and forth between your iPad and iTunes, they get bookmarked, so you can always pick up listening where you left off on either your iPad or in iTunes.

It’s easy to download apps and games directly on the iPad over its WiFi or 3G connection. You can also buy, download, and install new iPad programs from the big comfortable shopping window of iTunes—and then sync them all over to your connected iPad later. This sort of thing can be helpful if, say, you want a 300-megabyte birdwatching app that can take awhile to download on your iPad—besides, Apple currently limits individual App Store downloads to 20 MB over a 3G connection.

Syncing apps and games through iTunes has several other advantages. First, you get a backup copy of the file on your computer (and even in your computer’s backup file) instead of having it just on the iPad until you sync up again. Second, it’s easier to rearrange your apps with your iPad connected; iTunes displays all your iPad app screens at once, so you can click and drag the apps around in relation to other apps and screens. When you rearrange app icons on the iPad itself, you have to blindly drag them across each screen.

And third, if you have a bunch of space-hogging apps and an iPad with a small drive, you can sync the apps on and off the tablet as you need them. Turn on the checkboxes next to the apps and games you want to copy over and click Apply or Sync (or Apply and then Sync if you tinkered with the icon layout).

Apple has tried to make the whole getting-stuff-on-your-iPad process as simple and flexible as possible. Every once in awhile, though, minor hardware or software issues may trip up a smooth sync and make you wonder what’s making the iPad so unfriendly toward your files. These next couple of pages explain some of the more common problems—and how you fix them.

As mentioned earlier, you can use iTunes’ handy Home Sharing feature to stream media from your computer to your iPad over your home wireless network. Tapping into shared media libraries greatly increases your choice of audio and video files, and sharing’s especially useful if you have, say, a combined 500 GB of media across your network devices and only a 16 GB iPad.

To use Home Sharing, you need to turn it on in both iTunes and on your iPad, and you need to do the same on all the participating devices on your home wireless network. You also need an Apple Account ID. Here’s how to set it up:

Now it’s time to decide what to stream. For music, go to the iPad’s Home screen and tap the iPod icon. On the iPod screen, tap the Library icon on the top left side. In the box that pops up (shown here), tap the name of the library you want to sample. All the songs and playlists from that library now appear in iTunes, ready to play on your iPad.

To stream video, tap Home→Videos→Shared. Tap the square gray library icon so see all the TV shows, movies, music videos, and other clips available to watch. Tap a video thumbnail to stream the file to your iPad screen.

You can’t stream photos to the iPad with Home Sharing, but iTunes can beam them to a second-gen Apple TV. In iTunes, tap Advanced→“Choose Photos to Share” and turn on the checkboxes next to the photo albums you want to show off. Then use the Apple TV remote and its Photos menu to view them.

The iPad can pull in content from iTunes libraries, but it can also push out its own music, video, compatible apps, and photos to other devices with AirPlay, Apple’s technology for wirelessly streaming files to AirPlay-compatible speakers, stereos, and gadgets like Apple TV. A music system linked to the network through an Apple AirPort Express base station is also AirPlay-friendly.

Once you have your AirPlay-equipped device set up on your home network, pumping out the music, video, and photos from your iPad is easy. Just start up the file you want to stream, look for the AirPlay icon [] on the iPad’s screen and tap it. On the menu that drops down (shown at right), choose where you want to see or hear your selection, like “Apple TV” or “Basement Stereo.” Your song, video, or photo slideshow begins playing on the chosen system.

You control playback from the iPad itself. For audio and video, the standard old playback controls (, , , and ) appear on the iPad’s screen, letting you pause, play, and jump around in the content stream. As for photos, you simultaneously see your images on an Apple TV-connected television screen and on your iPad. You can swipe through them at your own pace, which makes it a snap to provide impromptu narration for your instant slideshow. If you created automatic slideshows on your iPad (Play Slideshows on Your iPad), you can beam those to the big screen through AirPlay as well.

When you’re done streaming and beaming, tap the AirPlay icon and tap iPad on the menu to return all your audio and video output to the tablet.