How to sync your iPhone and iPad using iTunes

As more and more of our data moves to Apple’s iCloud and other server-based services, it’s hard to believe that just a few years ago we relied solely on iTunes to keep our devices up-to-date with our content libraries. Even though iTunes’ role in managing iOS devices has diminished, Apple hasn’t completely abandoned syncing. Here’s a guide to doing it right.
When you first sync your iPhone, iPod touch, or iPad with iTunes, you must physically connect it to your computer via USB. (After you’ve synced for the first time, you can also enable Wi-Fi sync, which lets you connect to iTunes via Wi-Fi only.) Depending on what categories you select to sync, you can then load music, movies, apps, TV shows, ringtones, podcasts, books, and photos onto your device from your Mac. These might be ebooks you’ve bought on Amazon or music you’ve ripped yourself, in addition to any iTunes-purchased content.
In contrast, iCloud syncs only content you’ve purchased from iTunes and apps and app data from the App Store. iCloud lets you re-download, over the air, your purchased music, movies, apps, TV shows, ringtones, podcasts, and books from the iTunes or App Store. (If you subscribe to iCloud’s $25 per year iTunes Match service, you’ll also be able to sync up to 25,000 songs you own but that aren’t on the iTunes Store.) All other content that you’ve purchased or ripped elsewhere won’t be synced via iCloud, nor can Apple’s cloud service sync with your iPhoto or Aperture library.
If you have no content on your computer that you want to keep on your iOS device, you may not need to use iTunes at all. The majority of folks, however, will likely want content from both iCloud and their computer, and in that case they’ll need to use iTunes.

Here’s how iTunes offers a real advantage:
It lets you keep full backups of your app data so that you can restore a device faster than you can via iCloud: If you plan to buy a new iOS device, you can restore your purchased apps and content via iCloud—but that process can be very slow. If you use your computer and iTunes, however, a full iOS device restore will take minutes, not hours.
You can make encrypted local backups of your device: Want to make sure no one can crack open your backups? iTunes offers an encrypted-backups option that protects your backups with a password. (iCloud also encrypts your backups, but you again have to access them from a server, rather than store them locally.)

You can encrypt local backups with a password if you check the ‘Encrypt local backup’ checkbox.
You can easily rearrange your home screens and app layouts: Even in iOS 6 and Apple’s upcoming iOS 7, rearranging apps on new home screens can be a pain. iTunes offers a clickable rendition of your device’s home screen, where you can drag apps, create folders, and more, all with the click of a button.
You can add files to your apps: iTunes’ app file sharing lets you drag and copy files from your computer to specific apps on your iOS device; you can then view them on your iPhone or iPad. While Dropbox’s, Mail’s, and iOS’s respective ‘Open In’ commands make it relatively simple to add files to other apps on your iPhone or iPad, sometimes you might want to add a large file without sending it through Dropbox or Mail to add it to do so.
You can copy apps and their data: iCloud sync stores only your app’s data (game high scores, text files, saved passwords, and such) on its servers, not the apps themselves. When you need to restore your device, iCloud turns to the App Store to get the app. But if, for some reason, an app of yours gets removed from the iTunes Store, iCloud won’t be able to restore it.
If you sync your device with iTunes, however, all those apps and their data get copied to your computer for future restores, regardless of whether they’re still on the store. Granted, this takes up more space on your computer’s hard drive, but it ensures that an app you rely on won’t mysteriously vanish if you restore or upgrade your device.
If you want to enjoy your non-iTunes-purchased music, videos, books, or photos on your device, you must first make sure to import that content into iTunes on your computer.
To add an external media file to iTunes, simply drag it to the application’s Dock icon on your computer. Alternatively, with iTunes open, choose File > Add to Library and select the files.
When it comes to your photographs, iTunes sources images from either iPhoto, Aperture, a folder on your hard drive, or (for Windows users) Photoshop Elements 3 or later. To sync your images with your device, you’ll either need them to be in one of these programs or you’ll need to create a folder for them.
Not all media files play nice with iTunes: If you’re having a problem adding your content, check out our tips for troubleshooting music, video, ringtones, and ebook uploads.
Syncing your iPhone, iPod touch, or iPad with your computer is really quite easy. Gather  your device and its USB charging cable, and make sure you have installed the latest version of iTunes on your Mac. Plug in your device, and iTunes should launch, displaying your device’s summary screen.
If iTunes doesn’t immediately display your device, click the Devices button in the upper right corner of the iTunes window. (If you’re syncing more than one iOS device with the same computer, you’ll instead see a button called X Devices, where X is the number of devices you have.) Alternatively, select your device from the iTunes sidebar. If the sidebar isn’t visible, choose View > Show Sidebar.
To find options for what you can sync and how you sync it, click the tabs at the top of the iTunes window.
The summary screen offers a brief overview of your device, displaying its name, capacity, phone number (if applicable), serial number, and iOS version number. (Click the Summary tab if it isn’t displayed already.)
Here you can control how you back up your device. By default, iTunes asks you to choose one option (iCloud or your computer) for backing up. Still, if you choose to back up automatically via iCloud, you can always make an additional manual back up to iTunes by clicking the Back Up Now button you see here.

Check out an overview of your device in the summary screen.
Other options include syncing only checked songs and videos, syncing SD video over HD video, converting high-bit-rate music to lower-quality (and smaller) files for your device, and  specifying accessibility settings.
Additionally, if you’d like to use Wi-Fi Sync to connect your device wirelessly to iTunes in the future, click the ‘Sync with this [device type] over Wi-Fi’ checkbox.
The Info tab, at one point, was the main way to sync your contacts, calendars, and mail between your computer and your device. Now that most people have Google and iCloud accounts, however, this information usually syncs seamlessly over the air. If you’re using a service that won’t wirelessly sync with your device for whatever reason, you can manually sync it here, but most users should be able to ignore this pane entirely.
Click the Apps tab to see syncing options for all your apps. By default, any you’ve downloaded directly to your device are copied to iTunes when you sync (or if you’ve turned on Automatic Downloads in iTunes > Preferences > Store). On this page, iTunes lets you pick and choose the apps you’d like to sync, as well as rearrange your home screens.

Prune and rearrange apps during an iTunes sync using the Apps tab.
Make apps appear and disappear: A comprehensive list of all the apps you own shows up in a column on the left side of the pane; this includes iPhone-only apps, as well as iPad-only and Universal apps. You can sort these apps by name, kind, category, date, and size by using the pop-up menu above the list. To load an app onto your device, click the Install button to the right of the program’s icon; to remove the app, click the Remove button.
Below the list, you’ll see a checkbox that allows you to automatically sync any new apps you’ve purchased on your computer in the iTunes Store. (If you have Automatic Downloads enabled on your device, this checkbox is irrelevant, as any new purchases you make on your laptop or desktop will automatically download directly to your iPhone.)
Organize your home screens: On the right side of the Apps window is a preview of your device’s home screens. You’ll see a large, editable screen, as well as numbered thumbnails representing your other screens. Click a thumbnail to reveal it in the editing window. Here, you can click and drag an app’s icon to change its location. Or, if you see an app you’d like to remove, mouse over it and click the X that appears in the top left corner of the app icon.
Create folders: Still overwhelmed by your apps? Create folders to organize them. Drag one app onto another app; after a slight delay a folder appears with the two apps inside of it. The folder name is editable and you can rearrange icons within the folder.
Add files to some apps: Scroll down further on the Apps tab to access the File Sharing section. Some Apple and third-party apps allow you to add files from your computer via iTunes. (If you have no apps that support file sharing, this section won’t appear.) Click an app in the Apps list to see any files associated with it. To add a file, just drag it from your desktop or click the Add button.
Click the Music tab to see your options for tunes. To add nonpurchased music to your device, click the Sync Music checkbox. iTunes lets you choose between two options: copying your entire music library or copying selected playlists, artists, albums, and genres. You also have the option to include or exclude music videos and voice memos.

The Music tab lets you choose what tunes to sync with your iPhone or iPad: either everything or selected playlists, artists, albums, and genres.
Check for space: If you’re wary of sticking your whole music library on your device, you can preemptively see how much space it will take by looking at the capacity bar at the bottom of the iTunes window. When you select the Entire music library option, iTunes estimates how much space the files will take up and adjusts the bar accordingly. You can also see how many songs you’ll be loading in the upper right corner of the pane.
Fill extra space with surprises: If you decide to pick and choose, iTunes loads a complete list of your music for your perusal. Under the ‘Include music videos’ and “Include voice memos’ options, choose whether you’d like to fill any remaining free space with randomly selected music. Mix and match artists, playlists, albums, and genres by selecting the appropriate checkboxes.
For iTunes Match customers only: If you use iCloud’s $25 per year iTunes Match service, you won’t be able to sync your computer’s music. That’s because iTunes Match takes over the Music app when enabled, allowing you to stream music from your digital library rather than storing it locally on your iPhone, iPod, or iPad. iTunes will let you sync any voice memos you’ve made, but nothing beyond that. If you want to sync and store music on your device, just go to Settings > Music on the device and disable iTunes Match. When you next plug in your device, you should have access to all music sync options.
The Tones tab lets you sync ringtones you’ve created or purchased from the iTunes Store. (If you don’t have any, this pane won’t show up.) If you want to sync all your ringtones, select All Tones; otherwise, click Selected Tones.

Sync any ringtones you’ve purchased or made to your iPhone via the Tones tab.
When you click the Movies tab, you see a list of all the movies you have loaded into iTunes, represented by name and a movie poster or selected screenshot. This might include the latest movie you downloaded from iTunes to watch on the plane, as well as projects of yours that you’re carrying around just in case you catch a movie producer in an elevator.

The Movies tab lets you add movies to your device.
Click the Sync Movies checkbox, and you can automatically include all videos, selected videos, playlists, most recently uploaded videos, or unwatched videos. If you’ve rented movies from the iTunes Store on your computer, they appear at the very top of the screen. Transfer a movie to your iPhone or iPad by highlighting it, and then clicking the Move arrow. If you decide you don’t want to load the film on your device, click the arrow a second time.
As with the Movies tab, you see a list of your television shows, grouped by series, in the TV Shows tab.

In the TV Shows tab, you can add any shows you’ve purchased from iTunes.
Click a show and, in the right column, you see a list of its episodes, organized by season. When syncing manually, you can choose only individual episodes or seasons of selected shows. You can also copy over playlists that include TV episodes. If you choose to sync automatically, however, you can copy over an entire series (or your entire television library). You can also filter within that series to sync only unwatched or newly added episodes.
If you’ve rented TV shows on your computer from the iTunes Store, they appear at the very top of the TV Shows tab. Transfer one to your iPhone or iPad by clicking the Move arrow. You can remove it from your device by clicking the arrow a second time.
The Podcasts pane presents you with a list of all your subscribed podcasts, grouped by series. (If you haven’t subscribed to any, this pane won’t show up for you.) That said, this is one case when iTunes syncing may not be necessary. If you already have the Podcasts app on your iPhone or iPad, that will probably suffice.

Sync your played or unplayed podcasts automatically via the Podcasts tab.
Clicking a podcast displays a list of the show’s episodes, organized by date in ascending order. You can choose to sync your podcasts manually or use iTunes’ automatic options, which offer syncing for the most recently uploaded or unplayed episodes for selected shows or all shows.

The Books pane divides books and Audiobooks into two sections. Choose to sync All books or Selected books. You can peruse a list of your ePubs and PDFs if you want to pick and choose. The Sync Audiobooks pane is organized much the same way.
You can sync any books and PDFs you’ve added to iTunes via the Books tab.
Unlike your other content, your photos and personal video files are only linked to iTunes, rather than stored there. (Your original files remain in Apple’s iPhoto, Aperture, or the image folder you’re syncing with.)

The Photos tab syncs your images from iPhoto, Aperture, or a folder.
To sync photos, go to the Photos pane and choose the application or folder iTunes should link from. For example, if you keep all your images in iPhoto, enable the Sync Photos from option and choose iPhoto in the pop-up menu.
You can sync images according to how they are organized in that application. For example, if you use iPhoto, you’ll see images organized by date. Otherwise you can select only your Pictures folder or a custom folder of your choice.

Unfortunately, you can’t sync your iPhone or iPad with more than one program or with multiple folders. You have to choose one. As with all the other media panes, you can sync your entire photo library to your device or choose selected albums, projects, and (in iPhoto’s or Aperture’s case) Events, Faces, or images with certain star ratings. 

Keep iTunes metadata when you re-rip, and deauthorize missing Macs

In a grab-bag installment of The iTunes Guy, I look at how to ensure that tags and metadata get retained when you re-rip CDs, how to deauthorize computers for iTunes Store accounts, and how to change the name of your iTunes library for Home Sharing.

Q: I have a standard-quality MP3 album on my Mac that I’ve listened to for several years, added lyrics to, and so on. Now, because I discovered the Apple Lossless format and still have a CD of that album in my house, I would like to rip the CD again in higher quality. However, I don’t want to lose any of the metadata, because I have smart playlists that rely on the songs’ play count. Is it possible to do this without too much hassle?

It is. There is an easy (mostly reliable) way and a slightly more complicated (but better) way.

With this AppleScript, you can copy tags from older rips to newer, higher-quality rips and not lose any metadata.

The first method is to launch iTunes, insert the CD into your drive, and then check to see that all the tags—Album, Artist, Album Artist, Name, Genre, Composer—are exactly the same as yours. When you rip the CD again in Apple Lossless format, iTunes will ask if you want to replace the existing tracks. When it does so, it will keep your other tags, such as album art and lyrics, and iTunes-specific metadata, such as Last Played Date, Plays, Rating, and so on. However, in my experience, this method is hit-or-miss.

The second solution, which involves a few extra steps, always works for me. Begin by putting the MP3 files you plan to replace in a new or existing playlist. Now insert the CD in your drive, select it in iTunes, create another new playlist (or use another existing empty playlist), and drag the tracks from the CD’s window in iTunes to that playlist. Import the CD, and you’ll have two copies of the tracks: MP3 files in the first playlist and Apple Lossless files in the second.

Now download Doug Adams’s Copy Tag Info Tracks to Tracks AppleScript (donation requested). Select the first group of tracks (the MP3 files), and then launch the AppleScript. Put a checkmark next to each of the tags you want to copy (such as Plays), then click Proceed. Select the newly ripped (Apple Lossless) tracks and click Proceed again. The script will copy the selected tags to the new files, overwriting any tags they have.

Check the new files to make sure the tags and metadata are correct, and then delete the old files if you want to.

Q: How can I transfer my movies to the Home Videos section of my iTunes Movies library? In the older version of iTunes, there was no option for home movies. Now there’s one for both regular movies and home videos. My home videos are in the Movies section, and I’d like to move them to the Home Videos section.

This is quite simple. Select all the movies you want to change in iTunes, press Command-I, and click the Options tab in the Multiple Item Information window that appears. In the Media Kind pop-up menu, choose Home Video. iTunes will then move all those files to the Home Videos library.

The Media Kind menu lets you change which library a file is stored in.

Q: How do I deauthorize an iTunes account on a computer I no longer have? My old laptop doesn’t work, so I junked it, but I forgot to deauthorize my iTunes account on it.

Go to the main screen of the iTunes Store, and click Account under the Quick Links header. Enter your password where it’s requested, and you’ll be taken to your Account Information page. Look in the Apple ID Summary section at the top for Computer Authorizations. You’ll see how many computers are authorized. There’s no way to deauthorize a specific computer here, but you can click Deauthorize All to remove all of them. This is especially helpful if you sold or gave away your older computer and are worried someone might—inadvertently or otherwise—access your iTunes Store account. (Note that this option is available for you to use only once per year, and you won’t see it at all if you have fewer than two computers authorized.) Or if you’ve used fewer than the five total authorizations on your account, you can always just do nothing for the time being.

Once you deauthorize everything, you’ll need to reauthorize each computer that you currently use. You can do so in iTunes by going to Store > Authorize This Computer or by attempting to play any iTunes content with digital rights management (DRM)—such as videos or older iTunes music files. iTunes will then display a dialog box asking you to enter the password for that item’s Apple ID.

Q: I recently used Migration Assistant to move my files to my new iMac. I’ve noticed that while everything works great, including Home Sharing, the name that pops up on my devices while I’m accessing Home Sharing is still that of my old Mac, even though the one doing the sharing is definitely the new one. The hard drives have completely different names. Obviously, this is a minor concern, since everything is still working perfectly, but it’s driving me crazy trying to find the little preference I didn’t switch. Any ideas on how I can change this?

Yes, although the setting isn’t where might expect. If you open iTunes’ preferences (iTunes > Preferences), and click the Sharing tab, you’ll probably expect to see the name of your library there (in fact, I think it used to be there, in earlier versions of iTunes). But it’s not there.

Click the General tab instead, and you’ll see the library name. Enter a new name here and click OK.

The General preference pane has a field where you can name your iTunes library.

Note that this is not the name of your Mac, as defined in the Sharing pane of OS X’s System Preferences. If you wish, you can use the same name, but iTunes picks the user’s name—Kirk McElhearn’s Library, for example—by default to distinguish among what may be several libraries available on a Mac with multiple users.

[Ask the iTunes Guy is a regular column in which we answer your questions on everything iTunes related. If there’s something you’d like to know, send an email to the iTunes Guy for consideration.]

Follow me on Twitter @sajilpl

First 'Despicable Me' No. 1 on iTunes, Amazon

Steve Carell's Gru and his adorable minions aren't just taking over the box office, where Universal's Despicable Me 2 grossed $34.3 million on Wednesday.

The animated characters are also dominating digital downloads on iTunes, Amazon and Google's Play store.

The first Despicable Me movie is the No. 1 movie download on iTunes and Amazon as of Friday morning. The film is available to rent (starting at $2.99) and buy ($9.99) on both sites. The first movie is also the No. 9 rented title on Google Play ($2.99).

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Minion Madness, a 12-minute collection of mini movies about the minions is also making noise on the charts, landing at No. 14 on Google Play, No. 33 on iTunes and No. 75 on Amazon. Despite its higher placement on the Google Play chart, it costs $4.99 to buy there and $3.99 on iTunes and Amazon.

The Despicable Me game is also the top free iPhone app and No. 5 on Google Play's list of free Android apps.

STORY: 'Despicable Me 2': 5 Things to Know About the Minions

Meanwhile, preorders for the second film have already begun in earnest, with these advanced purchases putting Despicable Me 2 at No. 18 on Amazon's list of best-selling DVDs (where the first film is also No. 1) and No. 73 on iTunes' list of top movies.

iTunes features a Despicable Me 2 promotion on its main page, and Amazon has a promo on the main page for its Instant Video offerings.

Mac Gems: iFlicks tags and converts video files for iTunes with finesse

iFlicks 1.4 $20.00 iFlicks elegantly tags your TV shows and movies with online metadata, and can also convert video files to play in iTunes and sync with your iOS devices.

Get It for $20.00
There are plenty of apps that can transcode video from one format to another, and there are a number of nifty apps that let you tag media files with useful metadata. But Jendrik Bertram’s $20 iFlicks (Mac App Store link) does both, and I’ve found none better at combining the two tasks. iFlicks does its job with a clean, responsive, and very Mac-like interface that makes working with the software intuitive and fun.

Like the free Video Monkey, iFlicks can help you tag movies or TV shows you’ve ripped from your DVDs, recorded with an EyeTV-powered device, or downloaded from elsewhere—it supports adding artwork, genre, description, release date, episode titles and numbers, and more. It can also convert videos to smaller versions to save bits and bytes on space-crunched iOS devices, or to take files that iTunes can’t understand and make them playable on your Apple TV, to name just a couple examples. (As with other similar apps, iFlicks can convert only media files that aren’t protected with digital-rights-management [DRM] technology, which means it can't convert video purchased from the iTunes Store.)

The iFlicks window with items ready for tagging

iFlicks’s Preset pop-up menu, where you choose the output format for files you plan to process using the utility, offers nine options: Reference File, iTunes Compatible, Universal, iPod, iPhone, Apple TV, iPad, Apple TV 2, and New Apple TV & iPad. Most of the options are pretty self-explanatory, but it’s worth noting that the confusingly named iTunes Compatible option is what you use to add metadata without re-encoding. (It’s also worth noting that the iPhone preset maxes out at 480 by 360, so if you have an iPhone 4, 4S, or 5 or a recent iPod touch, you’ll want to choose the Apple TV preset, which provides a higher-quality video that still works with the latest iPhone models.) You can set any preset as the default.

The Destination pop-up menu lets you choose where you want iFlicks to save the resulting file: To your Movies folder, an iFlicks Folder inside the Movies folder, the same location as the original, or another location of your choosing.

iFlicks's preferences window

Click the Add To iTunes button (toggling the button to the “down” position) and iFlicks will copy the final file into iTunes (this option disables the Destination pop-up menu). Where, exactly, in iTunes? iFlicks’s preferences window lets you choose between the main iTunes library, a specific playlist, or an option called Add Videos To Playlists In The iFlicks Folder. With this option chosen, iFlicks creates a playlist folder in iTunes and populates that folder with two playlists: Movies and TV Shows. The utility then automatically places processed videos into the appropriate playlist in that folder.

A similar toggle button, Move Original to Trash, gives you the option to move the original file to the Trash when iFlicks finishes encoding/tagging it. That’s handy, and it’s also better than deleting the file outright just in case the resulting file is unplayable. (Some users have reported that some files won’t play after encoding/tagging—the even app warns you to back up your media files before using the app.) I’ve been using the app for several years now, and I’ve noticed such problems only on very rare occasion—and not at all with recent versions of the software—but it’s still better to be safe.

You can, of course, change these settings for each video you process, but if you tend to use the same settings every time, it’s easier to just configure everything at the start and then get to work.

When you drag a file or group of files into the iFlicks window, the software searches the TheTVDB.com and themoviedb.org online databases for matches with each file’s name—including, for TV shows, the season and episode numbers if part of the file name.

Searching for a match

If you don’t see the correct info for your file(s), you can click the Search For Details button at the bottom of the window (it looks like the non-standard OS X search button). In the window that appears, you can enter a new name to search—as you type, the app suggests titles that it thinks might match. You can toggle between TV Show and Movie results, and you can choose from among 23 different search languages.

When you find a match, click OK. You can then customize any of the fields to suit your needs before writing the metadata to your file. You can improve auto-detection by properly naming your media files (for example, futuramaS07E15) before dropping them into iFlicks.

Filling in the (metadata) blanks

If a file is already encoded in the proper format for your destination device, choosing the iTunes Compatible preset and clicking the Start button instantly writes the metadata to your files. Similarly, if you have iTunes-compatible files in an MKV container (such as HD video ripped from a Blu-ray movie that you own), iFlicks can handle tagging and prepping the video for iTunes using that same preset, though the process takes a little longer because iFlicks has to mux (join together) video and audio streams. (It still takes much less time than actually transcoding video.)

Alternatively, iFlicks can transcode video from one format to another. A common use of this feature is creating a file with a smaller frame size and bit rate—and, thus, a smaller file size—for portable devices. Thanks to the included open-source libavcodec, iFlicks is also useful for converting non-iTunes-compatible video files to something you can sync and watch on your iPad or Apple TV.

Although iFlicks offers lots of options for manually tweaking files, clicking the Rules button lets you configure some cool scripting features for automating such tweaks. For example, I have iFlicks set up so that if the show name (in the file name) contains Daily Show, iFlicks sets the show tag to The Daily Show with Jon Stewart, as that’s how the show is named in the TheTVDB.com database. Similarly, you could tell iFlicks to automatically set the artwork for a certain show or genre.

You can configure rules that iFlicks uses to process files.

The app includes a dozen pre-built scripts that are either complete (for example, setting the HD tag based on the file’s resolution) or half ready to go (identifying movie files of a particular genre, for example, with the outcome portion left blank for you to fill in).

It takes a little trial and error to get used to the app’s language—for example, name, show and filename are different input options whose differences may not be obvious—but when you figure it out these rules can automate some of the drudgery involved in tagging media files.

If you do a lot of video-file tagging and conversion, you’ll be hard-pressed to find another Mac app that performs these tasks as gracefully and as well as iFlicks. If you balk at the $20 price tag and need to tag files only occasionally, you can probably get by with Video Monkey, but with iFlicks you get what you pay for—a more capable and complete app.