Chapter 16. Syncing with iTunes

Just in case you’re one of the seven people who’ve never heard of it, iTunes is Apple’s multifunction, multimedia jukebox software. It’s been loading music onto iPods since the turn of the 21st century.

Most people use iTunes to manipulate their digital movies, photos, and music, from converting songs off a CD into music files to buying songs, audiobooks, and movies online.

But, as an iPhone owner, you need iTunes even more urgently, because it’s the most efficient way to get masses of music, videos, apps, email, addresses, ringtones, and other stuff onto the phone. It also backs up your iPhone automatically.

If you’ve never had a copy of iTunes on your computer, then fire up your web browser and go to www.apple.com/itunes/download. Once the file lands on your computer, double-click the installer icon and follow the onscreen instructions to add iTunes to your life.

Note

iTunes is not required. It’s perfectly possible to use all of an iPhone’s features without iTunes—even without a computer. You can download all that stuff right from the Internet, and you can back up your phone using iCloud (which is described in the next chapter).

Using iTunes, however, is more efficient, and it’s nice to know that your stuff is backed up on a machine that’s within your control. (For an overview of iTunes’ non-iPhone-related functions, like importing music and building playlists, see this chapter’s free Appendix, “iTunes Crash Course,” on this book’s “Missing CD” at www.missingmanuals.com.)

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Connecting the iPhone

iTunes is designed to load up, and back up, your iPhone. You can connect it to your computer either wirelessly over Wi-Fi, or wirefully, with the white USB cable that came with it.

Now open iTunes and click the (iPhone) button at the top-left corner of the iTunes screen. Now you can look over the iPhone’s contents or sync it (read on).

Note

If you have more than one iPhone, and they’re all connected, then this button is a pop-up menu. Choose the name of the one you want to manipulate.

On the Summary tab, scroll down; turn on Sync with this iPhone over Wi-Fi. Click Apply. You can now detach the phone.

From now on, whenever the phone is on the Wi-Fi network, it’s automatically connected to your computer, wirelessly. You don’t even have to think about it. (Well, OK—you have to think about leaving the computer turned on with iTunes open, which is something of a buzzkill.)

Transferring data between the iPhone and the computer is called synchronization. In general, syncing begins automatically when you connect the phone. The icon whirls in the top-left corner of the screen, but you’re welcome to keep using your iPhone while it syncs.

Note

Your photo-editing program (like Photos or Photoshop Elements) probably springs open every time you connect the iPhone, too. See Shutting Down the Importing Process if that bugs you.

Most people these days don’t bother with iTunes for syncing; they let the phone sync with their computers wirelessly, via free iCloud accounts.

If you’re a little queasy about letting a third party (Apple) store your personal data, though, you can also do this task manually. You can let the iPhone and your computer sync directly with each other—no Internet is involved.

Ordinarily, the iPhone-iTunes relationship is automatic, according to this scheme:

Tip

If you’re in a hurry, you can skip the time-consuming backup portion of the sync. Just click at the top of the iTunes window whenever it says “Backing up.” iTunes gets the message and skips right ahead to the next phase of the sync—transferring contacts, calendars, music, and so on.

OK, but what if you don’t want iTunes to fire up and start syncing every time you connect your iPhone? What if, for example, you want to change the assortment of music and video that’s about to get copied to it? Or what if you just want to connect the USB cable to charge the phone, not to sync it?

In that case, you can stop the autosyncing in any of these ways:

Of course, you must have turned off autosyncing for a reason. And that reason might be that you want to control what gets copied onto it. Maybe you’re in a hurry to leave for the airport, and you don’t have time to sit there for an hour while six downloaded movies get copied to the phone. Maybe you have 50 gigabytes of music but only 16 gigs of iPhone storage.

In any case, here are the two ways you can sync manually:

Now you can drag songs and videos directly onto the iPhone’s icon to copy them there. Wilder yet, you can bypass iTunes entirely by dragging music and video files from your computer’s desktop onto the iPhone’s icon. That’s handy when you’ve just inherited or downloaded a bunch of song files, converted a DVD to the iPhone’s video format, or whatever.

Just two notes of warning here. First, the iPhone accommodates dragged material from a single computer only. Second, if you ever turn off this option, all those manually dragged songs and videos will disappear from your iPhone at the next sync opportunity.

Tip

Also on the Summary tab, you’ll find the baffling little option called Sync only checked songs and videos. This is a global override—a last-ditch “Keep the embarrassing songs off my iPhone” option.

When this option is turned on, iTunes consults the tiny checkboxes next to every single song and video in your iTunes library. If you turn off a song’s checkbox, it will not get synced to your iPhone, no matter what—even if you use the Music tab to sync All songs or playlists, or explicitly turn on a playlist that contains this song. If the song’s or video’s checkbox isn’t checked in your Library list, then it will be left behind on your computer.

The Eight Great iTunes Tabs

Once your iPhone is connected to the computer, and you’ve clicked its icon in the upper-left corner of iTunes, the left side of the iTunes window reveals a column of word buttons: Summary, Apps, Music, Movies, TV Shows, Podcasts, Books, Photos, and Info. Below that is a second, duplicate listing, labeled On My Device. For the most part, these represent the categories of stuff you can sync to your iPhone.

The following pages cover each of these tabs, in sequence, and detail how to sync each kind of iPhone-friendly material.

Tip

At the bottom of the screen, a colorful graph shows you the number and types of files: Audio, Video, Photos, Apps, Books, Documents & Data, and Other (for your personal data). More importantly, it also shows you how much room you have left, so you won’t get overzealous in trying to load the thing up.

Point to each color block without clicking to see how many of each item there are (“2031 photos”) and how much space they take.

Summary Tab

This screen gives basic stats on your iPhone, like its serial number, capacity, and phone number. Buttons in the middle control how and where the iPhone gets backed up. Checkboxes at the bottom of the screen let you set up manual syncing, as described previously.

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If you click your phone’s serial number, it changes to reveal the unique device identifier (UDID). That’s Apple’s behind-the-scenes ID for your exact product, used primarily by software companies (developers). You may, during times of beta testing a new app or troubleshooting an existing one, be asked to supply your phone’s UDID.

You can click the same label again to see your phone’s Product Type and ECID. Or click your phone number to see your various cellular identifiers like the MEID, IMEI, and ICCID. Or click the iOS version to see your iOS version’s build number.

You can right-click (on the Mac, Control-click) any of these numbers to get the Copy command. It copies those long strings of letters and numbers onto your computer’s Clipboard, ready to paste into an email or a text.

Apps Tab

On this tab, you get a convenient duplicate of your iPhone’s Home screens. You can drag app icons around, create folders, and otherwise organize your Home life much faster than you’d be able to on the phone itself. See Rearranging/Deleting Apps Using iTunes for details.

Music Tab

Turn on Sync Music. Now decide what music to put on your phone.

Note

If you’re using iCloud Music Library (The Library Tab), this Music tab appears empty except for a note that you can play all your music wirelessly from the Internet. In other words, since all your music is online, there’s no point in choosing some subset of it to sync to your phone.

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Tip

Playlists make it fast and easy to sync whole batches of tunes over to your iPhone. But don’t forget that you can add individual songs, too, even if they’re not in any playlist. Just turn on Manually manage music and videos. Now you can drag individual songs and videos from your iTunes library onto the iPhone icon to install them there.

Music videos and voice memos (recorded by the iPhone and now residing on your computer) get their own checkboxes.

Sooner or later, everybody has to confront the fact that an iPhone holds only 16, 64, 128, or 256 gigabytes of music and video. (Actually less, because the operating system itself eats up over a gigabyte.)

Your multimedia stash may be bigger than that. If you just turn on Sync All checkboxes, an error message tells you that it won’t all fit on the iPhone.

One solution: Tiptoe through the tabs, turning off checkboxes and trying to sync until the “too much” error message goes away.

If you don’t have quite so much time, turn on Automatically fill free space with songs. It makes iTunes use artificial intelligence to load up your phone automatically, using your most played and most recent music as a guide. (It does not, in fact, fill the phone completely; it leaves a few hundred megabytes for safety—so you can download more stuff on the road, for example.)

Another helpful approach is to use the smart playlist, a music playlist that assembles itself based on criteria that you supply. For example:

  1. In iTunes, choose Music from the top-left pop-up menu. Choose File→New Smart Playlist.

    The Smart Playlist dialog box appears.

  2. Specify the category.

    Use the pop-up menus to choose, for example, a musical genre, or songs you’ve played recently, or haven’t played recently, or have rated highly.

  3. Turn on the “Limit to” checkbox, and set up the constraints.

    For example, you could limit the amount of music in this playlist to 2 gigabytes, chosen at random. That way, every time you sync, you’ll get a fresh, random supply of songs on your iPhone, with enough room left for some videos.

  4. Click OK.

    The new Smart Playlist appears in the list of playlists at left; you can rename it. Click it to look it over, if you like. Then, on the Music tab, choose this playlist for syncing to the iPhone.

Movies and TV Shows Tabs

TV shows and movies you’ve bought or rented from the iTunes Store look great on the iPhone screen. (And if you start watching a rented movie on your computer, the iPhone begins playing it right from where you left off.)

Syncing TV shows and movies works just like syncing music or podcasts. You can have iTunes copy all your stuff to the iPhone, but video fills up your storage fast. That’s why you can turn on the checkboxes of just the individual movies or shows (either seasons or episodes) you want—or, using the Automatically include pop-up menu, request only the most recent, or the most recent ones you haven’t seen yet.

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Podcasts Tab

The iTunes Store lists thousands of free amateur and professional podcasts (Podcasts). On this tab, you can choose to sync all podcast episodes, selected shows, all unplayed episodes—or just a certain number of episodes per sync. Individual checkboxes let you choose which podcast series get to come along for the ride, so you can sync to suit your mood at the time.

Books Tab

Here are the thumbnails of your audiobooks and your ebooks—those you’ve bought from Apple, those you’ve downloaded from the web, and those you’ve dragged right into iTunes from your desktop (PDF files, for example). You can ask iTunes to send them all to your phone—or only the ones whose checkboxes you turn on.

Tones Tab

Any ringtones that you’ve bought from the iTunes Store or made yourself (Caller ID) appear here; you can specify which ones you want synced to the iPhone. You can choose either All tones or, if space on your phone is an issue, Selected tones (and then turn on the ones you want).

Be sure to sync over any ringtones you’ve assigned to your frequent callers so the iPhone can alert you with a personalized audio cue, like Pink’s rendition of “Tell Me Something Good” when they call you up.

Photos Tab

Why corner people with your wallet to show them your kid’s baby pictures, when you can whip out your iPhone and dazzle them with a slideshow?

Syncing Photos and Videos (Computer→iPhone)

iTunes can sync the photos from your hard drive onto the iPhone. You can even select individual albums of images that you’ve already assembled on your computer.

Note

If you’ve turned on iCloud Photo Library (iCloud Photo Library), this tab appears blank. After all, your photos are already syncing.

Here are your photo-filling options for the iPhone:

Note

You can sync photos from only one computer. If you later attempt to snag some snaps from a second machine, iTunes warns you that you must first erase all the images that came from the original computer.

When you’re ready to sync your photos, click the Photos tab in iTunes. Turn on Sync photos from, and then indicate where you’d like to sync them from (Photoshop Elements, iPhoto, or whatever).

If you’ve chosen a photo-shoebox program’s name (and not a folder’s name), you can then click Selected albums, Events, and Faces. Turn on the checkboxes of the albums, events, and faces you want synced. (The “faces” option is available only if you’re syncing from Photos, iPhoto, or Aperture on the Mac, and only if you’ve used the Faces feature, which groups your photos according to who’s in them.)

This option also offers to tack on recent Events (batches of photos taken the same day). Indicate whether or not you want videos included in the syncing (Include videos).

Once you make your selections and click Apply, the program computes for a time, “optimizing” copies of your photos to make them look great on the iPhone (for example, downsizing them from 20-megapixel overkill to something more appropriate for a 0.6-megapixel screen), and then ports them over.

After the sync is complete, you’ll be able to wave your iPhone around, and people will beg to see your photos.

You can go the opposite direction, too: You can send photos and videos you took with the iPhone’s own camera to the computer. You can rest easy, knowing that they’re backed up to your computer for safekeeping.

Now, it’s important to understand that iTunes is not involved in this process. It doesn’t know anything about photos or videos from the iPhone.

So what’s handling the iPhone-to-computer transfer? Your operating system. It treats the iPhone as though it’s a digital camera and suggests importing them just as it would from a camera’s memory card.

Here’s how it goes: Plug the iPhone into the computer with the USB cable. What you’ll see is probably something like this:

Then again, some iPhone owners would rather not see some lumbering photo-management program firing itself up every time they connect the phone. You, too, might wish there were a way to stop iPhoto, Photos, or Windows from bugging you every time you connect the iPhone. That’s easy enough to change—if you know where to look.

From now on, no photo-importing message will appear when you plug in the iPhone. (You can always import its photos manually, of course.)

Info Tab

On this tab, you’re offered the chance to copy some distinctly non-entertainment data over to your iPhone: your computer’s calendar, address book, email settings, and web bookmarks.

Now, none of this setup is necessary if you use iCloud (Chapter 17), and you’ve told your phone to sync its calendar (in Settings→iCloud). That’s because iCloud, not iTunes, handles synchronization with the iPhone. Instead, this tab shows only a message that, for example, “Your calendars are being synced with your iPhone over the air from iCloud.”

Syncing Contacts and Calendars

If you’re not using iCloud syncing, then you can choose to sync your iPhone’s address book with a Windows program like Outlook, Outlook Express, or Windows Mail; a Mac program like Contacts or Entourage/Outlook for Mac; or an online address book like Google Contacts or Yahoo Address Book.

Similarly, you can sync the phone’s calendar with a program like Outlook (for Windows) or Calendar or Outlook (on the Mac).

On My Device

Below those Settings tabs at the left side of the iTunes window, there’s a second, similar set labeled On My Device. It’s a tidy list of everything that is, in fact, on your phone, organized by type (Music, Movies, and so on). There’s not really much you can do here—you can get more information about some items by pointing to them—but just seeing your multimedia empire arrayed before you can be very satisfying.

The Purchased category, in particular, can be handy; it shows everything on your phone that you’ve bought with the phone.

One iPhone, Multiple Computers

In general, Apple likes to keep things simple. Everything it ever says about the iPhone suggests that you can only sync one iPhone with one computer.

That’s not really true, however. You can actually sync an iPhone with multiple Macs or PCs.

And why would you want to do that? So you can fill it up with material from different places: music and video from a Mac at home; contacts, calendar, ebooks, and iPhone applications from your Windows PC at work; and maybe even the photos from your laptop.

iTunes derives these goodies from different sources to begin with—pictures from your photo program, addresses and appointments from your contacts and calendar programs, music and video from iTunes. So all you have to do is set up the tabs of each computer’s copy of iTunes to sync only certain kinds of material.

On the Mac, for example, you’d turn on the Sync checkboxes for only the Music, Podcasts, and Video tabs. Sync away.

Next, take the iPhone to the office; on your PC, turn on the Sync checkboxes on only the Info, Books, and Apps tabs. Sync away once more. Then, on the laptop, turn off Sync on all tabs except Photos.

And off you go. Each time you connect the iPhone to one of the computers, it syncs that data according to the preferences set in that copy of iTunes.

One Computer, Multiple iPhones

It’s fine to sync multiple iPhones with a single computer, too. iTunes cheerfully fills each one up, and can back each one up, as they come. In fact, if you open the Preferences box (in the iTunes menu on the Mac, the Edit menu in Windows), the Devices tab lists all the iPhones that iTunes is tracking (and iPads and iPod Touches).

Backing Up the iPhone

iTunes can back up everything your computer doesn’t already have a copy of: stuff you downloaded straight to the phone (music, ebooks, apps, and so on), plus less visible things, like your iPhone’s mail and network settings, your call history, contact favorites, notes, text messages, and other personal preferences that are hard or impossible to recreate.

Tip

If you turn on the Encrypted iPhone Backup option, then your backup will include all your passwords: for Wi-Fi hotspots, websites, email accounts, and so on. That can save you tons of time when you have to restore the phone from the backup. (The one downside: You’ll be asked to make up a password for the backup. Don’t forget it!)

You can create your backups in either of two places:

You make this choice on the Summary tab described earlier in this chapter.

So the day has come when you really need to use that backup of your iPhone. Maybe it’s become unstable, and it’s crashing all over. Or maybe you just lost the dang thing, and you wish your replacement iPhone could have all your old info and settings on it. Here’s how to save the day (and your data):

  1. Connect the iPhone to the computer you normally use to sync with.

  2. Click the (iPhone) button; click the Summary tab.

  3. Click Restore iPhone.

    A message announces that you can’t erase the phone without first turning off Find My iPhone. This is a security measure to stop a thief from erasing a stolen phone. He can’t restore the phone without turning off Find My iPhone, which requires your iCloud password. Go to the phone and do that (in Settings→iCloud).

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  4. Take iTunes up on its offer to restore all your settings and stuff from the backup.

    If you see multiple backup files listed from other iPhones (or an iPod Touch), be sure to pick the backup file for your phone. Let the backup restore your phone settings and info. Then resync all your music, videos, and podcasts. Exhale.

To save disk space, you can delete old backups (especially for i-gadgets you no longer own). Go to the iTunes preferences (Edit→Preferences in Windows or iTunes→Preferences on the Mac) and click the Devices tab.

Click the dated backup file you don’t want and hit Delete Backup.