ITUNES IS YOUR IPAD’S best friend. You can do just about everything with your digital files here—convert songs on a CD into iPad-ready tunes, buy music, listen to Internet radio stations, watch videos, and more. Here’s a quick tour of the main iTunes window and what all the buttons and sliders do.

All your iTunes media libraries can be found under the Library pop-up menu on the far left side of the window. Click the pop-up menu button to open it. Select a library (like Music) to display its contents in the iTunes window, like so:

The outer edges of the iTunes window are full of buttons and controls. Here’s what they do:

Next, there’s the horizontal row of buttons under the iTunes playback controls.

MUSIC, VIDEOS, APPS, AND other content you download from the iTunes Store land in their respective libraries—songs in the Music library, Hawaii Five-0 episodes in TV Shows, and so on. Just click the Library pop-up menu in the top-left corner to jump between media types. You’ll find copies of songs or videos you bought in the Purchased lists under the Playlists button, 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 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 where it belongs—movies in Movies, ebooks in Books, and so on.

In the iTunes window, click the file you want to reassign and choose File→Get Info (or press Ctrl-I [⌘-I]) to call up the Info box. Click the Options tab and then, next to the label “Media Kind,” select the appropriate category from the pop-up menu (see below). Then click OK.

BEHIND ITS STEELY SILVER-FRAMED window, iTunes stores your music, movies, and everything else you add to it inside its own iTunes folder on your hard drive (which, unless you moved it, is in Music→iTunes [Home→Music→iTunes]). If you’re running Windows 8, Windows 7, or Windows Vista, your iTunes folder is at User→[User Name]→Music→iTunes, and Windows XP users can find it at My Documents→My Music→iTunes.

I nside the iTunes folder, you’ll find your iTunes library file, called iTunes Library.itl (or iTunes Library on Macs with old versions of iTunes), a database that contains the names of all the songs, playlists, videos, and other content you added to iTunes. Be careful not to move or delete this file if you poke around in the folder. If iTunes can’t find the file, it gives a little sigh and creates a new list—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 or show it. That’s because iTunes 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 button on the right side of the main iTunes window and you land in the Store’s virtual aisles. They’re jam-packed with digital merchandise, all filed by category across the top of the main window: Music, Movies, TV Shows, App Store, Books, Podcasts, and so on. 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 directly to a subcategory within the section (Blues in Music, for example). Done shopping? Click the Library button to leave the Store.

The iTunes Store window highlights iTunes’ latest audio and video releases and specials. Here are a few tips for shopping the Store:

If your iPad is in range of a wireless or cellular-data network, you have another way to get to the Store: over the airwaves, as explained next.

WITH AN IPAD, YOU don’t even need your stodgy old computer to shop the iTunes Store—you can tap your way into it right over a wireless Internet or 4G/3G connection. Many WiFi–enabled Starbucks coffee shops also let you browse and buy in the iTunes Store, including the music playing right there at Starbucks.

To buy stuff on your iPad when you’re out 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 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 the Purchased playlist. You can also turn on Automatic Downloads to snag it—or just grab it right from iCloud (Use iTunes in the Cloud).

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 WiFi 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 that happens, don’t worry. iTunes is designed to pick up the download 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 use this same link to check for available purchases any time you think you might have something waiting, like a new episode from a TV Show Season Pass or a pre-ordered album.

APPLE’S USAGE AGREEMENT LETS you play Store purchases on up to five computers: Windows PCs, Macs, or any combination of them. 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 ID and password on each computer to authorize it to play songs, videos, and 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 ID. To authorize another computer, choose Store→Authorize This Computer on that Windows PC or Mac.

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 Library menu. Click the triangle beside the House icon to get to 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 Import if you want to automatically copy certain types of files, like music, among these machines—and eventually over to your iPad.

APPLE LETS YOU PLAY your iTunes Store purchases on up to five computers. You won’t be able to play purchased music, books, or videos on a sixth computer if you try to authorize it. That’s because Apple’s authorization system will see five other computers already on its list and deny your request.

To play protected files on Computer Number 6, you have to deauthorize another computer. Choose Store→Deauthorize This Computer from the computer about to get the boot, and then type in your Apple ID 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 the machine so your new one will be able to play copy-protected files. Erasing a hard drive, by itself, doesn’t deauthorize 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:

Note that you only see this button if you’ve hit the five-computer limit—and you can use it just once a year. Once you deauthorize all your machines, go back to the computers in your Home Sharing network and re-authorize each one.

WHEN IT COMES TO syncing content to your iPad, iTunes 11 offers several ways to move your media from computer to tablet. If you want to automatically copy all your music or every podcast in your library each time you sync up, you have two ways to do that. (Want to pick and choose what goes on that iPad? Turn the page for more selective syncing options.)

To copy everything in a certain library, Music for example, each time you sync:

If you don’t want to go through the steps to automatically sync each media type—and you have a small iTunes library, or one set up just for the iPad (Set Up Multiple iTunes Libraries)—click the Summary tab with your iPad connected. In the Options area, remove the check in the box next to “Manually manage music and videos.” Click the Apply and then the Sync button to move everything to the iPad (if it fits).

IF YOU OPT OUT of autosyncing your iPad or your media doesn’t fit, you now need to choose songs or videos for it. Until you do, your iPad just sits there, empty and forlorn in your iTunes window, waiting for you to give it something to play with. You can manually sync using the USB cable or over the WiFi airwaves (Sync Your iPad with iTunes).

Manual Method #1

1. Click the iPad icon at the top of the iTunes window. That opens up a world of syncing preferences.

2. Click the Music tab, and then turn on the “Sync Music” checkbox.

3. Click the button next to “Selected playlists, artists, and genres” and check off the items you want to copy to your iPad. (No playlists? See Chapter 13.)

4. Click the Apply button at the bottom of the iTunes window. (As the rest of this chapter explains, the steps are similar for movies, TV shows, and so on.)

EVERY ONCE IN A while, minor hardware or software issues may trip up a smooth sync. Here are some of the more common problems—and how to fix them.

IT’S SIMPLE TO BUY digital goods from the iTunes Store, but how do you easily get the stuff you buy on one gadget onto all your iOS devices and computers? That’s where Apple’s iTunes in the Cloud service comes in. It acts as an online backup service for all the music, apps, video, and books you buy. Once you buy something from the Store, iTunes in the Cloud knows it and can download copies to all the devices and computers that use the same Apple ID. As with many things in the Appleverse (as well as automobiles), you have two ways to copy files across devices: automatic and manual. Here’s how to do either:

To get selective on the iPad, tap iTunes open from the Home screen and then tap the Purchased icon at the bottom of the Store screen. Tap All to see everything you’ve ever bought or “Not on this iPad” to see just a list of the things missing from the tablet. Tap the cloud icon and type in your Apple ID and password to download the stuff to your iPad.

iCloud in the iTunes 11 Library

IF YOU’VE BEEN USING iTunes for a few years and upgraded to iTunes 11, you may notice little cloud icons ( or ) on or next to some of the items within your library—or even next to your Library pop-up menu. This isn’t a meteorological commentary on your taste in music and video. This is iCloud keeping track of the items you previously bought with your Apple ID. It lets you know that, hey, just because you bought and downloaded that Eric Clapton album on your work computer doesn’t mean you have to go all the way to the iTunes Store to click on the Purchased link to manually download it to this iTunes library.

To download the item when you’re in album view, roll the mouse over the k icon. This gives you a icon, which you can then click to begin the download. (If you skip the chance to download the item and move on, the icon reverts back to .)Other libraries, like TV Shows, just show the icon next to the available items, as shown below.

When iTunes is downloading files, you see a small icon up in the right side of the iTunes window; click it to see how much longer you have to wait.

If you purposefully keep your iTunes purchases on separate machines and don’t want to see clouds on virtual library items everywhere you look, turn off the fluffy icons and ignore those purchases by choosing View→Hide Music in the Cloud. That way, you’ll see only the songs residing on your current computer.

AS MENTIONED EARLIER, you can use iTunes’ handy Home Sharing feature to stream media from a sharing 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 is especially useful if you have, say, a combined 500 gigabytes of media across your network devices and only a 16 GB iPad.

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

Now it’s time to decide what to stream to your iPad. For music, go to the iPad’s Home screen and tap the Music icon. On the Music screen, tap the More button at the bottom of the screen. In the box that pops up, tap Shared (shown below-left), and then tap the name of the library you want to sample (right). All the songs and playlists from that library now appear on your iPad’s iTunes list, ready to play.

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

Photo Sharing with iTunes

You can’t stream photos to the iPad with Home Sharing, but iTunes can beam them to a second-gen (or later) Apple TV. In iTunes, tap File→Home Sharing→Choose Photos to Share. In the box that appears (below), choose the photo albums or folders you want to see. Then use the Apple TV remote, go to its Photos menu, find your newly shared photos, and view them on your TV.

You can even set your Apple TV to use your shared photos as a screensaver. On your Apple TV’s main screen, go to Settings→Screen Saver→Photos. Choose your computer from the list, and then select the photo folder, iPhoto event, or other collection that the screen saver can grab for those quiet moments.

THE IPAD CAN PULL in content from shared iTunes libraries, but it can also push out its own music, videos, compatible apps, and photos to other devices via AirPlay, Apple’s technology for wirelessly streaming files to compatible audio gear and gadgets, like Apple TV. For example, with an Apple TV (second-generation or later) connected to an HDTV, you can share your videos, photos, and music with everyone else in the room.

As of iOS 5 or later, you can even mirror (duplicate) whatever is on your iPad 2, third- or fourth-generation iPad, or iPad Mini’s screen to the TV—which is great for gaming, presentations, or showing off fancy apps. 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 picture from your iPad is easy. Start up the file you want to stream, find the AirPlay icon ()on the iPad’s screen, and tap it. On the menu that appears (shown below), choose where you want to see or hear your selection, like “Apple TV.” Your song, video, or photo slideshow begins playing there.

You can also get the AirPlay controls by double-clicking the iPad’s Home button and flicking left to right as far as you can go along the row of apps at the bottom of the screen. The images on the opposite page show the buttons.

Even when you beam your media to an Apple TV, you control playback from the iPad itself. For audio and video, the standard old playback controls (, , , and ) appear on the iPad’s screen (shown right) so you can play, pause, and jump around in the content. As for photos, you simultaneously see your pics on an Apple TV-connected television screen and on your iPad. You can swipe through them at your own pace, providing impromptu narration for your slideshow. If you created automatic slideshows on your iPad (Play Slideshows on Your TV), you can beam ’em to the big screen through AirPlay, too.

Video Mirroring

To turn on video mirroring for games and other apps, double-click the iPad’s Home button to summon the playback controls in the app panel (shown below). Tap the AirPlay icon, turn on mirroring, and then tap to choose your preferred viewing screen. The faster the WiFi network, the smoother the playback, so consider a speedy 802.11n router if you need some zip.

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

EVER HAVE ITUNES BLASTING out your whole library on shuffle—and find yourself curious about the next song in the rotation? Maybe it’s a track you’re not in the mood for at the moment. You can sneak a peak at the upcoming song (and several others after it) with the new Up Next feature built into iTunes 11.

To use Up Next while iTunes is playing, click the icon in the display area of the iTunes window, as shown below. The Up Next list pops up to reveal what’s, well, up next in your music queue as you listen to your tunes.

Up Next can do a lot for your impromptu music-management whims:

Even better, you can add songs from Up Next playlists to your connected iPad. Just click to see the list of pending tracks. Click the icon next to a song or album you want to add to the iPad and then choose Add To from the menu. On the Add To submenu, select your iPad to copy the tracks.

YOU MAY BE SAYING to yourself, “Well, this iTunes in the Cloud thing is great in case my hard drive ever croaks, but I didn’t buy everything in my library from the iTunes Store. What about all the tracks I ripped from my CD collection?” You have two options here:

For home-ripped tracks that the iTunes Store also sells (it has 28 million songs), iTunes Match adds new Store copies to your iCloud account. For more obscure tracks, ones that the Store doesn’t sell, iTunes Match uploads a copy of each rare gem from your computer to your iCloud account (and yes, that means Apple is wading around in your personal music files).

To use iTunes Match, you need an Apple ID (Set Up an Apple ID), an Internet connection, and an iPad, iPhone, or iPod Touch running iOS 5 or later. Then there’s the money part—you also need a credit card to pay $24.99 a year for a subscription, which covers up to 25,000 songs. And finally, you need some time while iTunes Match uploads your rare tracks to iCloud.

To sign up for iTunes Match, open iTunes on your computer, choose Store→Turn On iTunes Match, and then click the Subscribe button. After you sign up, your music and playlists are added to your big giant iCloud library, including any tracks that iTunes had to upload.

Now you need to get the iPad into the mix. Tap Settings→Music. Flip on iTunes Match. While this initially removes all the songs from your iPad, you can grab them again by tapping the Cloud icon. To see the tracks you’ve already downloaded, along with tracks you can download, tap Settings→Music→Show All Music→On.

Once you pony up the $25 for iTunes Match, you get on-the-go access to your entire music library, along with your Genius Playlists and Genius Mixes, from your iPad or any other ’Net-connected iOS 5 or later device.