Synchronizing Media with Your iPhone

The brainy Phone app and the sleek Safari browser may earn the lion's share of kudos for the iPhone, but many people reserve their rave reviews for its Music app. The darn thing is just so versatile! It can play music, of course, but it also happily cranks out audiobooks and podcasts, as well as music videos, movies, and TV shows.

If there's a problem with this digital largesse, it's that the Music app might be too versatile. Even if you have a big 64GB iPhone, you may still find its confines a bit cramped, particularly if you're also loading up your iPhone with photos, contacts, and calendars, and you just can't seem to keep your hands out of the App Store cookie jar.

All this means is that you probably have to pay a bit more attention when it comes to syncing your iPhone, and the following sections show you how to do just that.

Syncing music and music videos

The Music app is a digital music player at heart, so you've probably already loaded up your iPhone with lots of audio content and music videos. To get the most out of the Music app's music and video capabilities, you need to know all the ways you can synchronize these items. For example, if you use the Music app primarily as a music player and your iPhone has more disk capacity than you need for all your digital audio, feel free to throw all your music onto the player. On the other hand, your iPhone might not have much free space, or you might only want certain songs and videos on the player to make it easier to navigate. Not a problem! You can configure iTunes to sync only the songs that you select.

Syncing playlists is that you can estimate in advance how much space your selected playlists will usurp on the iPhone. In iTunes, click the playlist and then examine the status bar, which tells you the number of songs in the playlist, its total duration, and - most significantly - its total size.

Before getting to the specific sync steps, you need to know that there are three ways to manually sync music and music videos:

Playlists. With this method, you specify the playlists that you want iTunes to sync. Those playlists also appear on your iPhone's Music app. This is by far the easiest way to manually sync music and music videos because you usually just have a few playlists to select. The downside is if you have large playlists and run out of space on your iPhone, the only way to fix the problem is to remove an entire playlist. Another bummer with this method is that you can only sync all or none of your music videos.
Check boxes. With this method, you specify which songs and music videos are synced by selecting the little check boxes that appear beside every song and video in iTunes. This is precise syncing for sure, but because your iPhone can hold thousands of songs, it's also a lot of work.
Drag and drop. With this method, you click and drag individual songs and music videos, and drop them on the iPhone icon in the iTunes Devices list. This is an easy way to get a bunch of tracks on your iPhone quickly. However, iTunes doesn't give you any way of tracking which files you've dragged and dropped.

What do you do if you only want to select a few tracks from a large playlist? Waste a big chunk of your life deselecting a few hundred check boxes? Pass. Here's a better way: Press ?+A (Mac) or Ctrl+A (Windows) to select every track, right-click any track, and then click Uncheck Selection. iTunes deselects every track in seconds flat. Now you can select only the tracks you want. You're welcome.

Here are the steps to follow to sync music and music videos using playlists:

In iTunes, click your iPhone in the Devices list.
Click the Music tab.
Select the Sync Music check box. iTunes asks you to confirm that you want to sync music.
Click Sync Music.
Select the Selected playlists, artists, albums, and genres option.
Select the check box beside each playlist, artist, album, and genre you want to sync.
Select the Include music videos check box if you also want to add your music videos into the sync mix.
Select the Include voice memos check box if you also want to sync voice memos recorded on your iPhone.
If you have lots of music that has been ripped at a high bit rate (say, 256 Kbps or higher), those songs will take up a lot of space on your iPhone. To fix this, click the Summary tab and then select the Convert higher bit rate songs to X AAC check box, where X is the converted bit rate you want to use: 128, 192, or 256 Kbps.
If you want iTunes to fill up any remaining free space on your iPhone with a selection of related music from your Library, select the Automatically fill free space with songs check box.
Click Apply. iTunes syncs your iPhone using the new settings.

Here are the steps to follow to sync using the check boxes that appear beside each track in your iTunes Music Library:

In iTunes, click your iPhone in the Devices list.
Click the Summary tab.
Select the Sync only checked songs and videos check box.
Click Apply. If iTunes starts syncing your iPhone, click the Cancel button (X) in the iTunes status window to stop it.
Either click Music in the Library list or click a playlist that contains the tracks you want to sync. If a track's check box is selected, iTunes syncs it with your iPhone. If a track's check box is deselected, iTunes doesn't sync it with your iPhone. If the track is already on your iPhone, iTunes removes it.
In the Devices list, click your iPhone.
Click the Summary tab.
Click Sync. iTunes syncs just the selected tracks.

If you download a music video from the web and then import it into iTunes (by choosing File ? Import), iTunes adds the video to its Movies library. To display it in the Music library instead, open the Movies library, right-click the music video, and then click Get Info. Click the Video tab and use the Kind list to choose Music Video. Click OK. iTunes moves the music video to the Music folder.

You can also configure iTunes to let you drag tracks from the Music library (or any playlist) and drop them on your iPhone. Here's how this works:

In iTunes, click your iPhone in the Devices list.
Click the Summary tab.
Select the Manually manage music and videos check box.
Note:
When you select the Manually manage music and videos check box, iTunes automatically deselects the Sync music check box in the Music tab. However, iTunes doesn't mess with the music on your iPhone. Even when it syncs after a drag and drop, it only adds the new tracks - it doesn't delete any of your phone's existing music.
Click Apply. If iTunes starts syncing your iPhone, click the Cancel button (X) in the iTunes status window.
Either click Music in the Library list or click a playlist that contains the tracks you want to sync.
Choose the tracks you want to sync:
- If all the tracks are together, Shift+click the first track, hold down Shift, and then click the last track.
- If the tracks are scattered all over the place and click each track.
Click and drag the selected tracks to the Devices list and drop them on the iPhone icon. iTunes syncs the selected tracks.

If you decide to return to playlist syncing by selecting the Sync music check box in the Music tab, iTunes removes all tracks that you added to your iPhone via the drag-and-drop method.

Syncing podcasts

In many ways, podcasts are the most problematic of the various media you can sync with your iPhone. Not that the podcasts themselves pose any concern. Quite the contrary: they're so addictive that it's not unusual to collect them by the dozens. Why is that a problem? Because most professional podcasts are at least a few megabytes in size and many are tens of megabytes. A large-enough collection can put a serious dent in your iPhone's remaining storage space.

All the more reason to take control of the podcast syncing process. Here's how you do it:

In iTunes, click your iPhone in the Devices list.
Click the Podcasts tab.
Select the Sync Podcasts check box.
If you want iTunes to choose some of the podcasts automatically, select the Automatically include check box and proceed to Steps 5 and 6. If you prefer to choose all the podcasts manually, deselect the Automatically include check box and skip to Step 7.
Choose an option from the first pop-up menu:
- All. Choose this item to sync every podcast.
- X most recent. Choose this item to sync the X most recent podcasts (where X is a number you choose).
- All unplayed. Choose this item to sync all the podcasts you haven't yet played.
- X most recent unplayed. Choose this item to sync the X most recent podcasts that you haven't yet played.
- X least recent unplayed. Choose this item to sync the X oldest podcasts that you haven't yet played.
- All new. Choose this item to sync all the podcasts published since the last sync.
- X most recent new. Choose this item to sync the X most recent podcasts published since the last sync.
- X least recent new. Choose this item to sync the X oldest podcasts published since the last sync.
  Note:
  A podcast episode is unplayed if you haven't yet played at least part of it, either in iTunes or on your iPhone. If you play an episode on your iPhone, the player sends this information to iTunes when you next sync. Even better, your iPhone also lets iTunes know if you paused in the middle of an episode, so when you play that episode in iTunes, it starts at the point where you left off.
Choose an option from the second pop-up menu:
- All podcasts. Select this to apply the option from Step 5 to all your podcasts.
- Selected podcasts. Select this to apply the option from Step 5 only to the podcasts you select.
Select the check box beside any podcast or podcast episode you want to sync.
Click Apply. iTunes syncs the iPhone using your new podcast settings.

To mark a podcast episode as unplayed, in iTunes choose the Podcasts library, right-click the episode, and then choose Mark as New.

Syncing audiobooks

The iTunes sync settings for your iPhone have tabs for Music, Photos, Podcasts, and Video, but not one for Audiobooks. What's up with that? It's not, as you might think, some sort of antibook conspiracy or even forgetfulness on the part of Apple. Instead, iTunes treats audiobook content as a special type of book (not surprisingly). To get audiobooks on your iPhone, follow these steps:

In iTunes, click your iPhone in the Devices list.
Click the Books tab.
Select the Sync Audiobooks check box.
Select the Selected audiobooks option.
Select the check box beside each audiobook you want to sync.
Click Apply. iTunes syncs your audiobooks to your iPhone.

Syncing movies

It wasn't all that long ago when technology prognosticators and pundits laughed at the idea of people watching movies on a 2-inch by 3-inch screen. Who could stand to watch even a music video on such a tiny screen? The pundits were wrong, of course, because now it's not at all unusual for people to use their iPhones to watch not only music videos but also short films, animated shorts, and even full-length movies.

The major problem with movies is that their file size tends to be quite large - even short films lasting just a few minutes weigh in at dozens of megabytes, and full-length movies are several gigabytes. Clearly there's a compelling need to manage your movies to avoid filling up your iPhone and leaving no room for the latest album from your favorite band.

Follow these steps to configure and run the movie synchronization:

In iTunes, click your iPhone in the Devices list.
Click the Movies tab.
Select the Sync Movies check box. iTunes asks you to confirm that you want to sync movies.
Click Sync Movies.
If you want iTunes to choose some of the movies automatically, select the Automatically include check box and proceed to Step 6. If you prefer to choose all the movies manually, deselect the Automatically include check box and skip to Step 7.
Choose an option from the pop-up menu:
- All. Choose this item to sync every movie.
- X most recent. Choose this item to sync the X most recent movies you've added to iTunes (where X is a number you choose).
- All unwatched. Choose this item to sync all the movies you haven't yet played.
- X most recent unwatched. Choose this item to sync the X most recent movies you haven't yet played.
- X least recent unwatched. Choose this item to sync the X oldest movies you haven't yet played.
Select the check box beside any other movie you want to sync.
A movie is unwatched if you haven't yet viewed it either in iTunes or on your iPhone. If you watch a movie on your iPhone, the player sends this information to iTunes when you next sync.
If you want to watch rented movies on your iPhone, in the Rented Movies section, click the Move button beside the rented movie you want to shift to your iPhone. iTunes adds it to the On iPhone list (where iPhone is the name of your iPhone).
Click Apply. iTunes syncs the iPhone using your new movie settings.

Syncing TV show episodes

If the average iPhone is at risk of being filled by a few large movie files, it's probably also at grave risk of being overwhelmed by a large number of TV show episodes. A single half-hour episode can eat up approximately 250MB, with HD versions weighing in at closer to 650MB, so even a modest collection of shows will consume multiple gigabytes of precious iPhone space.

This means it's crucial to monitor your TV episode collection and keep your iPhone synced with only the episodes you need. Fortunately, iTunes gives you a decent set of tools to handle this:

In iTunes, click your iPhone in the Devices list.
Click the TV Shows tab.
Select the Sync TV Shows check box. iTunes asks you to confirm that you want to sync TV shows.
Click Sync TV Shows.
If you want iTunes to choose some of the episodes automatically, select the Automatically include check box and proceed to Steps 6 and 7. If you prefer to choose all the episodes manually, deselect the Automatically include check box and skip to Step 8.
Choose an option from the pop-up menu:
- All. Choose this item to sync every TV show episode.
- X newest. Choose this item to sync the X most recent episodes (where X is a number you choose).
- All unwatched. Choose this item to sync all the episodes you haven't yet viewed.
- X newest unwatched. Choose this item to sync the X most recent episodes that you haven't yet viewed.
- X oldest unwatched. Choose this item to sync the X oldest episodes that you haven't yet viewed.
  A TV episode is unwatched if you haven't yet viewed it either in iTunes or on your iPhone. If you watch an episode on your iPhone, the player sends this information to iTunes when you next sync.
Choose an option from the second pop-up menu:
- All shows. Select this option to apply the choice from Step 6 to all your TV shows.
- Selected shows. Select this option to apply the choice from Step 6 to only the TV shows you select.
Select the check box beside any TV show or episode you want to sync.

To mark a TV episode as unwatched, in iTunes choose the TV Shows library, right-click the episode, and then choose Mark as New.

Syncing e-books

If you've used your computer to purchase e-books from the iTunes Store or to add some downloaded e-books to the iTunes library, you'll want to get those onto your iPhone as soon as possible. Similarly, if you've grabbed some e-books from the iBookstore on your iPhone, it's a good idea to back them up to your computer.

You can do both by syncing e-books between your computer and your iPhone:

In iTunes, click your iPhone in the Devices list.
Click the Books tab.
Select the Sync Books check box.
In the book list, select the check box beside each book that you want to sync.
Click Apply. iTunes syncs the iPhone using your new books settings.
Click Apply. iTunes syncs the iPhone using your new TV show settings.

Syncing computer photos to your iPhone

No media collection on an iPhone is complete without a few choice photos to show off around the water cooler. One way to get those photos is to take them with the built-in digital cameras on your iPhone. However, if you have some good pics on your computer, you can use iTunes to send them to the iPhone. Note that Apple supports a number of image file types in addition to the most common TIFF and JPEG formats, including BMP, GIF, JPG2000 or JP2, PICT, PNG, PSD, and SGI.

Note:
If you have another photo-editing application installed on your computer, chances are it will also appear in the Sync photos from list.

If you use your computer to process lots of photos and you want to take copies of some (or all) of them with you on your iPhone, then follow these steps to sync them:

In iTunes, click your iPhone in the Devices list.
Click the Photos tab.
Select the Sync Photos from check box.
Choose an option from the pop-up menu:
- iPhoto (Mac only). Choose this item to sync the photos, albums, and events you've set up in iPhoto.
- Choose folder. Choose this command to sync the images contained in a folder you specify.
- Pictures (or My Pictures in some versions of Windows). Choose this item to sync the images in the Pictures (or My Pictures) folder.
Select the photos you want to sync. The controls you see depend on what you chose in Step 4:
- If you chose iPhoto. In this case, you get two further options: Select the All photos, albums, Events, and Faces option to sync your entire iPhoto library. Select the Selected albums, Events, and Faces option, and then select the check box beside each item you want to sync.
- If you chose either Pictures or Choose folder. In this case, select either the All photos option or the Selected folders option. If you select the latter, select the check box beside each subfolder you want to sync.
Click Apply. iTunes syncs the iPhone using your new photo settings.

Note:
iTunes doesn't sync exact copies of your photos to the iPhone. Instead, it creates what Apple calls TV-quality versions of each image. These are copies of the images that have been reduced in size to match the iPhone screen size. This not only makes the sync go faster, but it also means the photos take up much less room on your iPhone.

Syncing iPhone photos to your computer

If you create a Safari bookmark on your iPhone and then sync with your computer, that bookmark is transferred from the iPhone to the default web browser on your computer. That's a sweet deal, and it also applies to contacts and appointments. Unfortunately, it doesn't apply to media files that, with one exception, travel along a one-way street from your computer to your iPhone.

But then there's that one exception, and it's a good one. If you take any photos using your iPhone's built-in cameras, the sync process reverses itself and enables you to send some (or all) of those images to your computer.

Note:
Actually, there's a second exception to the one-way media syncing rule. If you use the iTunes app on your iPhone to purchase or download music, those files are transferred to your computer during the next sync. iTunes creates a Store category called Purchased on iPhone (where iPhone is the name of your iPhone). When the sync is complete, you can find your music there, as well as in the Music library.

The iPhone-to-computer sync process bypasses iTunes entirely. Instead, your computer deals directly with your iPhone and treats it just as though it was some garden-variety digital camera. How this works depends on whether your computer is a Mac or a Windows PC, so I use separate sets of steps.

To sync your iPhone camera photos to your Mac, follow these steps:

Connect your iPhone to your Mac. iPhoto opens, adds your iPhone to the Devices list, and displays the photos from your iPhone's Camera Roll album.
Use the Add event name text box to name the event that these photos represent.
If you don't want iPhoto to split the synced photos into multiple events based on the date each photo was taken, deselect the Split Events check box.
Choose how you want to import the photos:
- If you want to import every photo, click Import X Photos, where X is the number of photos in your iPhone's Camera Roll. Technically, it's the number of photos in your iPhone's Camera Roll that you haven't previously imported. Any photos that you've already imported appear separately in the Already Imported section.
- If you want to import only some of the photos, select those you want and then click Import Selected.
Using the dialog that appears after the import is complete, choose what you want iPhoto to do with the photos on your iPhone:
- If you want to leave the photos on your iPhone, click Keep Photos.
- If you prefer to clear the photos from your iPhone, click Delete Photos.

Here's how things work if you're syncing with a Windows 8 or Windows 7 PC (these steps assume you've installed Windows Live Photo Gallery from the Windows Live Essentials site):

If you don't have Windows Live Photo Gallery installed, you can still access your iPhone photos in Windows 8 or 7. In Windows 8, click Desktop, click Windows Explorer, and then click Computer; in Windows 7, choose Start ? Computer. Double-click your iPhone in the Portable Devices group. Open the Internal Storage folder, then the DCIM folder, and then the folder that appears (which will have a name such as 800AAAAA). Your iPhone photos appear and you can then copy them to your computer.

Connect your iPhone to your Windows PC.
Open Windows Live Photo Gallery.
Choose Home ? Import. The Import Photos and Videos dialog box appears.
Click the icon for your iPhone, and then click Import. Windows Live Photo Gallery connects to your iPhone to gather the photo information.
Select the Import all new Items now option. If you'd prefer to select the photos you want to import, select the Review, organize and group Items to import option. Then click Next, use the dialog box to choose the photos you want, and skip to Step 7.
Type a tag for the photos. A tag is a word or short phrase that identifies the photos.
Click Import. Windows Live Photo Gallery imports the photos.

Here's how things work if you're syncing with a Windows Vista PC:

Connect your iPhone to your Windows Vista PC. The AutoPlay dialog box appears.
Click Import pictures using Windows. The rest of these steps assume you selected this option. However, if you have another photo-management application installed, it should appear in the AutoPlay list. Click it to import photos via that program.
Type a tag for the photos. A tag is a word or short phrase that identifies the photos.
Click Import. Vista imports the photos and then opens Windows Photo Gallery to display them.

Note:
Configuring your computer not to download photos from your iPhone means that in the future, you'll either need to reverse the setting to get photos or manually import them.

Syncing photos via iCloud

Syncing photos from your computer isn't difficult, but it seems more than a little old-fashioned in this increasingly wireless age. Fortunately, if you have an iCloud account, you can place your feet firmly in the modern era by using the Photo Stream feature to sync photos without even looking at a USB cable. Photo Stream automatically syncs photos you take using your iPhone cameras to your iCloud account, which then downloads them to your computer, your iPad, or any other device associated with your account. Similarly, if you upload photos to iCloud using another device, those photos are synced automatically to your iPhone.

Follow these steps to activate Photo Stream on your iPhone:

In the iPhone Home screen, tap Settings. The Settings app appears.
Tap Photos & Camera.
Tap the My Photo Stream switch to On.

Preventing your iPhone from sendingphotos to your computer

Each time you connect your iPhone to your computer, you see iPhoto (on your Mac), the AutoPlay dialog box (in Windows 8, 7, or Vista), or the Scanner and Camera Wizard (in Windows XP). This is certainly convenient if you actually want to send photos to your computer, but you might find that you only do that once in a blue moon. In that case, having to deal with iPhoto or a dialog box every time could cause even the most mild-mannered among us to start pulling hair out.

If you prefer to keep your hair, you can configure your computer not to pester you about getting photos from your iPhone.

Here's how you set this up on your Mac:

Choose Launchpad → Other → Image Capture. The Image Capture application opens.
In the Devices list, click your iPhone.
Click the Connecting this iPhone opens menu, and then choose No application.
Choose Image Capture → Quit Image Capture. Image Capture saves the new setting and then shuts down. The next time you connect your iPhone, iPhoto ignores it.

Follow these steps to convince Windows 8, Windows 7, and Windows Vista not to open the AutoPlay dialog box each time you connect your iPhone:

Open the Default Programs window:
- Windows 8. In the Start screen, type default and then click Default Programs.
- Windows 7 or Windows Vista. Choose Start ? Default Programs to open the Default Programs window.
Click Change AutoPlay settings. The AutoPlay dialog box appears.
In the Devices section, open the Apple iPhone list and choose Take no action.
Click Save. Windows saves the new setting. The next time you connect your iPhone, you won't be bothered by the AutoPlay dialog box.

Syncing media with two or more computers

It's a major drag, but you can't sync the same type of content to your iPhone from more than one computer. For example, suppose you're syncing photos from your desktop computer. If you then connect your iPhone to another computer (your notebook, for example), crank up iTunes, and then select the Sync photos from check box, iTunes coughs up the dialog. As you can see, iTunes is telling you that if you go ahead with the photo sync on this computer, it will blow away all your existing iPhone photos and albums!

So there's no chance of syncing the same iPhone with two different computers, right? Not so fast, my friend! Let's try another thought experiment. Suppose you're syncing your iPhone with your desktop computer, but you're not syncing movies. Once again, you connect your iPhone to your notebook computer (or whatever), crank up iTunes, and then select the Sync movies check box. Hey, no ominous warning dialog! What gives?

The deal here is that if iTunes sees that you don't have any examples of a particular type of content (such as movies) on your iPhone, it lets you sync that type of content, no questions asked.

In other words, you can sync your iPhone with multiple computers, although in a roundabout kind of way. The secret is to have no overlapping content types on the various computers you use for the syncing. For example, let's say you have a home desktop computer, a notebook computer, and a work desktop computer. Here's a sample scenario for syncing your iPhone with all three machines:

Home desktop (music and video only). Select the Sync Music check box in the Music tab, and select the Sync Movies check box in the Movies tab. Deselect the Sync Photos and Sync Podcasts check boxes on the Photos and Podcasts tabs, respectively.
Notebook (photos only). Select the Sync Photos check box on the Photos tab. Deselect all the Sync check boxes in the Music, Podcasts, and Movies tabs.
Work desktop (podcasts only). Select the Sync Podcasts check box in the Podcasts tab. Deselect the Sync check boxes in the Music, Photos, and Movies tabs.