The Beginner’s Guide to iTunes

For those new to the world of iTunes, the task of getting media content loaded onto your iPod, iPhone or iPad can be a daunting one. Even if you have a lot of experience in other media applications, the way in which Apple has approached media management in the world of the iPod and iTunes may differ significantly from what you’ve become accustomed to.

This tutorial will provide the information that both the novice and experienced computer user may find useful as they take their first trepidatious foray into the world of iTunes and Apple’s media devices, including where to get music and video content from, how to get it onto your device, and how to manage and organize it once it’s there.

The Beginner’s Guide to iTunes
iTunes and Apple’s Philosophy of Media Management

Prior to delving into filling your iPod or iOS device it is important to understand that Apple takes a considerably different approach from most other media software and hardware products in terms of how your content is managed—both on your computer and on the device itself.

Content on an iPod or iOS device is managed via Apple’s iTunes software application, which is a free download from Apple’s web site. However, iTunes is more than just a means of loading your device. It is in fact an entire media management system that is designed to organize and catalog your music, audiobooks, videos, podcasts, and even handle your iBooks and iOS applications. In fact, iTunes doesn’t even require that the user have an iPod or other Apple media device, and there are people out there who choose to use iTunes simply as their media management application.

Philosophically, the iTunes library is treated as the central point of all media content—your master library, if you will—and devices such as the iPod, iPhone, iPad and Apple TV are considered extensions of this core iTunes library. The idea here is that you manage the content in a master library on your computer, and carry around portions of it on your portable device. This is different from the concept of the portable media player being its own library that users familiar with other media products have probably become accustomed to.

In its default configuration, iTunes automatically synchronizes your library (or a portion thereof), to your media device. Once setup, this happens transparently and automatically each time you connect the device to your computer. Again, the iPod or iOS device becomes an extension of your main library, rather than a library unto itself.

That said, iTunes does provide a method for users who would rather not maintain an iTunes library on their local computer, but simply want to manually transfer music from one or more computers to their device on an as-required basis. We will discuss these options in more detail further on in this article.

Regardless of the method used, generally the first step in getting content onto your iPod is to get it into your iTunes library. In fact, if you do not yet own an iPod but are planning to buy one, you can even download iTunes in advance and start importing your media content and getting your library ready for your iPod. Then, when you finally do get your iPod, filling it up is generally as simple as connecting it to your computer and letting iTunes do the rest.

iCloud and iTunes Match

In June 2011, Apple introduced iCloud, its new online service that covers a variety of applications. This also includes iTunes Match, a subscription-based service that essentially stored your iTunes library on the iCloud servers. Although iTunes Match allows users to effectively sync with an online version of their iTunes library, the service does not eliminate the need to import your music into an iTunes library to get it onto the iCloud servers in the first place. Further, the iTunes application is still required to actually manage the iCloud-based library.

It’s all about the Music…

Today’s iPod models and iOS devices can play music, audiobooks, podcasts, videos, and even display your photo collection and run applications. However, despite all of these different types of content and features, the core focus remains on music, and most iPod and iPhone owners will be concerned first and foremost with getting their existing music collection onto their device.

One of the common myths about the iPod is that you have to buy your music from the iTunes Store. This stems at least partly from the fact that iTunes is actually both the name of Apple’s media management application and the name of Apple’s online media service, and also partly from the fact that some of Apple’s competitors have propagated this myth in the past by implying that it costs a lot of money to fill an iPod.

In reality, nothing could be further from the truth. iTunes can easily import content from commercial or self-created audio CDs, or any standard MP3 file that you may have available. Purchasing content from the iTunes Store is far from the only option, and there are many iPod and iTunes users with large music collections who have never purchased even a single track from the iTunes Store. Further, as more online digital music stores begin adopting open DRM-free standards, you have many other choices for where to purchase music, even for online download. Our Guide to Purchasing Music Online provides more detail on the various options available ranging from the iTunes Store to other services like Amazon and Walmart.

However, since most people who buy an iPod probably already own at least some music on compact disc (CD), this is usually a good place to start. iTunes provides built-in features for loading your CDs into directly into your music library, and if you have an Internet connection it can even look up track information for most commercial CDs and fill it for you automatically, ensuring that any tracks you import are properly labelled.

iTunes can also natively import any files that are already in the AAC or MP3 format which can be obtained from any number of online sources. Our Guide to Free Music for your iPod discusses a number of options for obtaining free legal digital music downloads, and a Consolidated List of Free Music Websites can also be found in our iLounge Discussion Forums.

In fact, the only real limitation with regards to iTunes’ support for digital music formats is the Windows Media Audio (WMA) format. Neither iTunes nor any of Apple’s media devices natively support this format, although iTunes will helpfully offer to convert any unprotected WMA files that you ask it to import. Unfortunately, if you have purchased files in the Windows Media Audio (WMA) format from other online music services, iTunes will not be able to convert these directly due to the Digital Rights Management (DRM) restrictions on these files. If your DRM license permits, you can burn these to an audio CD using another compatible media application and then import that audio CD into iTunes as you would for any commercial audio CD. It’s also worth noting that WMA conversion is only available if you’re using iTunes on Windows, since Mac OS X doesn’t include the necessarily Microsoft Windows Media Player libraries to handle the conversion.

The iTunes Store is certainly a convenient option for purchasing digital music, and this is even more true with Apple’s transition to an entirely DRM-free music catalogue in early 2009. Music available on the iTunes Store is no longer protected by any Digital Rights Management (DRM), and therefore any concern about only being able to use your purchased music on Apple devices is no longer an issue. Tracks purchased from the iTunes Store are tagged with your iTunes Store account information for various reasons such as keeping track of your purchases within the iTunes application, but even this information can be easily removed by a third-party application if it’s really a serious privacy concern. Keep in mind though that the DRM-free catalog only applies to music files; other content types such as audiobooks, movies, and TV shows remain DRM protected.

Importing existing digital music files into iTunes
This section provides information for users who have an existing collection of digital music files that they would like to add to their iTunes library. New users who are starting out with no digital music files can skip ahead to the next section on importing CDs into iTunes.

The first time you run iTunes you will be given the option of scanning your home folder for any compatible audio files and importing them into your iTunes library. You can let iTunes do this for you, or you can skip this step and add these files manually later. If you let iTunes scan your hard drive for audio files, you may end up with a lot more than you anticipated. Many games and other applications will have soundtracks and effects tracks stored in the MP3 format within their program folders, and iTunes may end up adding these to your library along with your normal music files.

Further, you may wish to adjust some of iTunes’ settings prior to this first import. We generally recommend that users skip this initial import process. Don’t worry, it’s just as simple to scan your hard drive and add these files in later, after you know what you may be getting yourself into.

For users with a relatively small number of digital music files, the default options will normally suffice, and there’s probably no need to be concerned with the more detailed information explained below.

However, for those users who already have a large collection of existing digital music files, it is important to first understand how iTunes handles this process, and where you may want to adjust some settings before importing. Although the default import options should get your music into iTunes with a minimum of effort, a little bit of pre-planning can ensure that your music library is more manageable in the long run, and can avoid surprises later on.

Note that iTunes’ default behavior for importing music files is slightly different on Windows than it is on the Mac.

For Mac users, the default is for iTunes to store all of the media files that you add to your iTunes library in the “iTunes Media” folder which is stored under an “iTunes” folder in your home directory’s Music folder. When you add existing files to the iTunes library, these files are copied from their present location into the iTunes Media folder. This means that if you are importing a large music collection, you will need enough disk space to make a complete copy of it during this process. Once your music has been added to iTunes and copied into the iTunes Media folder, you can delete the original files, however.

For Windows users, iTunes also creates an itunes Media Folder in “iTunes\iTunes Media” under your Windows Music folder, but by default it does not copy existing digital media files into this location—it simply leaves them where they are and references them from there.

This allows Windows users coming from another media management application to more easily preserve their existing file and folder structure, but can make managing your iTunes library more complicated in the longer term, particularly if you need to move it to another hard drive or computer in the future.

The location of the iTunes Media folder and whether added files are copied or not can be adjusted through iTunes’ advanced preferences, which can be accessed from the iTunes, Preferences menu on Mac OS X, or the Edit, Preferences menu on Windows. Simply select the “Advanced” button in the iTunes Preferences dialog box:


The Copy files to iTunes Media folder when adding to library option determines whether iTunes copies added files into the music folder path or simply references them from their original locations. This option is enabled by default for Mac users, and disabled by default for Windows users, as noted earlier.

The Keep iTunes Media folder organized option determines whether iTunes will attempt to reorganize files within the iTunes Media folder as the track information is modified in iTunes. With this option enabled, iTunes will read the ARTIST, ALBUM, and TRACK name information from your music files, for example, and use this to organize them into a sub-folder structure in the form of ARTIST/ALBUM/TRACKNAME. This naming behavior is hard-coded and cannot be customized. Note that this only affects existing files that are already in the iTunes Media folder. Files copied into the media folder as they are added are always placed in the organized location, since they have to go somewhere. Similar file and folder naming conventions are used for other types of media—SHOW/SEASON/EPISODENAME for TV shows, for instance.

Also keep in mind that regardless of the “Keep organized” setting above, iTunes will never attempt to move, rename, or delete any files that are located outside of the iTunes Media folder; iTunes treats the media folder as its “home” directory and any files that are not stored in this location are considered to be outside of its control.

With the “Copy files” and “Keep organized” settings enabled, iTunes is designed to insulate the average user from the underlying file system, taking care of all of the details of how your media files are stored for you so that you don’t normally have to worry about it. As changes are made to track information within the iTunes library, iTunes automatically reorganizes your media files appropriately.

Unless you have a very specific reason to maintain your own file and folder structure, such as using it with another media application, we strongly recommend allowing iTunes to copy files into your iTunes Media folder and manage them. This will save many headaches in the longer term, especially if you ever need to move your iTunes library to a different partition, hard drive, or computer.

Once you’ve reviewed these settings and decided how you would like your media files to be organized, you can begin the process of adding existing files to your iTunes library simply by selecting the appropriate option from the File menu in iTunes. This is another area where Windows and Mac versions differ slightly—Mac users simply get a single Add to Library option, whereas Windows users must choose between Add File to Library and Add Folder to Library.


The Beginner’s Guide to iTunes


The Beginner’s Guide to iTunes

Regardless of which operating system or method you use, however, the concept is the same—simply select a file, files, or a folder to add to your library, and iTunes does the rest. Note that if you are selecting a folder, all sub-folders are included as well.

Another method for adding music files to your iTunes library is simply to drag and drop either individual files, a group of files, or a folder right into the iTunes window. These files will be added to the iTunes library in the same way that the File menu options work.

As of iTunes 9, you can also find a sub-folder in your main iTunes Media folder named “Automatically Add to iTunes.” As the name implies, anything dropped into this folder is automatically imported into your iTunes library. Note that since this folder is in the iTunes Media folder, any files dropped in here will be moved out and organized into the iTunes Media folder regardless of the iTunes preferences above.

It is important to note that iTunes for Windows does not track files that are renamed or moved outside of iTunes. The iTunes library stores the full path and filename of each file that has been imported into the iTunes library and renaming or moving that file will cause iTunes to lose track of it. If you plan to use your own file and folder structure, this should ideally be established before you import these tracks into the iTunes library.

Mac users can get away with renaming and moving files around on the same drive as the OS X operating system handles this. However, OS X only tracks file moves on the same drive or partition—moving a file to another drive will still result in a broken link in iTunes.

Importing CDs into iTunes

For many, purchasing a new iPod, iPhone or iPad may be their first journey into the world of digital music, and they won’t already have a large existing library of content. However just about everybody has a few CDs that they want to get into their iTunes library.

The good news is that importing a CD into your iTunes library is generally as simple as inserting the CD and letting iTunes do the rest. By default, when you insert a CD, iTunes detects it, looks up its track information online and asks you if you want to import it:


The Beginner’s Guide to iTunes

Simply select “Yes” and iTunes will import the tracks into your iTunes library, storing them as 256kbps AAC files in your iTunes Media folder.


The Beginner’s Guide to iTunes

When you insert a CD, iTunes will attempt to look up information on the CD using the Gracenote CD Database (CDDB). If multiple matches are found, it will prompt you to select the correct one:


The Beginner’s Guide to iTunes

If iTunes cannot find any matches, then it will inform you of this, and ask you if you want to import the songs anyway. In this case, you might want to answer “No” so that you can enter information for the CD manually before proceeding to import it.


The Beginner’s Guide to iTunes

All of these settings can be further tweaked in your iTunes preferences. On the General tab you can specify how iTunes behaves when you insert an audio CD:


The Beginner’s Guide to iTunes

The When you Insert a CD setting allows you to specify what iTunes should do when it detects that you’ve insert an audio CD. The first three options are relatively self-explanatory, allowing you to choose to do nothing more than simply show the CD content, start playing the CD, or automatically import the CD. The fourth option, “Import CD and Eject” provides a very efficient way to import a large number of CDs; in this mode, iTunes will automatically import any audio CD that you insert and eject it when it’s finished. This allows you to easily just keep feeding CDs into your computer and letting iTunes work through them in the background while you’re working on something else.


The Beginner’s Guide to iTunes

The Automatically retrieve CD track names from Internet allows you to disable the CDDB lookup for newly-inserted CDs. Note that you can always initiate a manual lookup of CD information from the iTunes Advanced menu. Lastly, the Import Settings button opens a new window that allows you to specify your default audio file format and bit-rate for your imported CDs.


The Beginner’s Guide to iTunes

iTunes supports the AAC, AIFF, Apple Lossless, MP3 and WAV file formats. Presets are provided for each format that should meet a typical user’s needs, although you can choose to customize your import settings more precisely if you so desire by selecting the “Custom” option in the Settings drop-down menu.


The Beginner’s Guide to iTunes

Although there is much debate and discussion about the merits of various audio formats and bit-rates, a simple rule of thumb is that iTunes’ AAC encoder will produce slightly better quality audio files at a given bit-rate (ie, file size) than iTunes’ MP3 encoder will, but you will sacrifice compatibility with other digital audio hardware and software players, as MP3 is a much more widely-supported format.

In short, if you only intend to play your imported music through iTunes or on your iPod or other Apple device then you can select the AAC format. For a more compatible library with other hardware and software, you will probably want to use the MP3 format.

The other formats (AIFF, Apple Lossless and WAV) will create significantly larger file sizes, as these are essentially “lossless” compression. These formats are generally only of interest to higher-end users and audiophiles.

More information and discussion on the various audio file formats can be found in our Digital Audio Formats forum in the iLounge Discussion Forums.

Buying Digital Music

Another possible source of music for your Apple media devices is online music stores such as the iTunes Store itself or other third-party digital music services such as Amazon or Walmart.

The iTunes Store works within the iTunes software application, and any music purchased from the iTunes Store is automatically downloaded and added to your iTunes library. More detailed information on purchasing content from the iTunes Store can be found in our Complete Guide to Using the iTunes Store.

Note that some commercial digital music services still use the Protected WMA format for their music, which is not compatible with iTunes or any of Apple’s media devices. However, the industry has in general been moving away from protected music formats, and services such as eMusic ( and Amazon MP3 ( now offer digital music for sale in a non-DRM-protected standard MP3 format. These files contain no copy protection or other restrictions, and can be played on any player which supports the almost-universal MP3 file format. Our Guide to Purchasing Music Online provides more information on the various online music stores that are compatible with iTunes and Apple’s media devices.

Music purchased from other online sources will simply be downloaded to your hard drive, and must be added manually to iTunes in the same way as any other digital music file.


iTunes and Apple’s media devices also provide support for audiobooks purchased from the iTunes Store or from and e-books purchased from Apple’s own iBookstore. Audiobooks can be downloaded or imported directly into iTunes, and listened to via iTunes or on your iPod or other Apple media device. Note that audiobooks from are not compatible with the Apple TV.

You can also import your own books on CD into your iTunes library in much the same way as you would import any other CD.

These will not be organized into the “Books” section in iTunes by default, however, but will be treated as music files. In recent versions of iTunes, however, you can easily catalogue these imported files as audiobooks.

iBooks (or simple “Books” as Apple refers to them) can be purchased and downloaded in iTunes for synchronization to an iPhone, iPod touch or iPad using the iBooks app. You can also import your own Books in either PDF or ePub format for syncing to your iOS device. Note that ePub Books—purchased or imported—can be read only on an iOS device and not directly in iTunes.

For more information on book support in iTunes and on Apple’s media devices, including instructions for how to convert your own books into iTunes, see our Complete Guide to iTunes Books, Podcasts + iTunes U and our Books and Spoken Word forum in the iLounge Discussion Forums.

Podcasts and iTunes U

Another great source of content can be found in the iTunes Podcast directory and the iTunes U educational section within the iTunes Store. Podcasts are audio or video tracks, usually of an episodic nature, that you subscribe to. These are available on a wide range of topics such as news broadcasts, talk radio shows, music, audio and video blogs and games and hobbies. iTunes U content is similar in concept to podcasts, but these are distributed by educational institutions such as colleges and universities and contain educational content and course materials.


The Beginner’s Guide to iTunes

Podcasts and iTunes U are accessed via the iTunes Store, however they are generally available at no cost. In fact, Apple really only provides the catalog for this content; the actual podcast and iTunes U files are downloaded directly by the iTunes application from the provider’s own web site.

Once you subscribe to a podcast or iTunes U collection, iTunes will automatically download new episodes as they become available, and transfer these to your iPod or iOS device if you have configured it to do so.

For more information on podcast support in iTunes and on Apple’s media devices, see our Complete Guide to iTunes Books, Podcasts + iTunes U and our Podcasts & Podcasting forum in the iLounge Discussion Forums.

Organizing It All

Once you have imported your media into your iTunes library, you may still need to organize it to make your content easier to find. iTunes and Apple’s media devices index your music by tag information contained within the files such as artist, album, and track name, rather than simply by file and directory name. Music imported from CD or purchased from legitimate online digital music stores should already have this information correctly filled in. However, often users who have collected music files from a variety of different sources may find that the information contained within the files themselves is inaccurate or incomplete. This information can be cleaned up in iTunes itself simply by selecting a file or group of files and choosing Get Info from the iTunes File menu, which will present a dialog box where you can edit the information for that track or group of tracks.


The Beginner’s Guide to iTunes

Alternatively there are a number of third-party tools available that can help to automatically transfer a file/folder naming structure into the internal tag information within the files themselves. Tag & Rename ($30, 30-day trial available) or MP3Tag (donation-ware).

For users who don’t even have a reliable file and folder naming structure there are also more sophisticated third-party tools available such as SongGenie ($30) that can actually analyze your music tracks to attempt to identify them and apply proper name, artist and album information.

With the obvious exception of the iPod shuffle, all of Apple’s current media devices also offer the ability to displayed album artwork for your tracks. iTunes can automatically search for missing artwork for your music assuming that the album and artist information is accurate. This feature requires an iTunes Store account, but is free to use. Alternatively, artwork can be added manually through each track’s file information properties, in the same way that other tags are edited.

In addition to organizing the tag information within files themselves, it may also be desirable to create playlists within the iTunes application to organize your favorite songs, or select groupings of music to transfer to your device. To create a playlist, simply choose File, New Playlist from within iTunes. You can then add content to the playlist by dragging and dropping it from your main iTunes library window. The advantage of playlists is that these not only organize your music for listening purposes, but they can also be used as a method for automatically synchronizing only selected content from your iTunes library onto your iPod or iOS device. This is especially useful when you have a library that is significantly larger than the capacity of your device.

iTunes also offers a more advanced type of playlist—the Smart Playlist. This is a dynamic playlist that you can create which automatically selects tracks based on search criteria you specify, and when combined with iTunes’ ratings and play tracking features can be easily setup to create dynamic playlists to keep your iPod content fresh.

For more information on tagging your music tracks, adding album artwork to them, and creating playlists, see our Complete Guide to Album Tagging, Art and Playlists in iTunes.

Putting it on your iPod, iPhone or iPad

Once you’ve collected some media content in your iTunes library and you’ve unwrapped your new iPod, iPhone or iPad, the next step is to get it onto your device. Again, this is an area where iTunes makes things very simple if you already have an organized iTunes library.

Simply connect your iPod or iOS device to your computer. By default, iTunes will detect the new device, and take you through some initial screens to set it up.


The Beginner’s Guide to iTunes

From here you can specify a name for your new device and choose what content you want iTunes to automatically sync, if any. Note that you can easily rename your device later simply by double-clicking on it in the iTunes Devices list to edit the name and typing in a new name.

If your iPod or iOS device is large enough to hold your entire iTunes library, this is really the only step. Click “Done” and iTunes will proceed to synchronize your entire library onto your device, including any playlists that you have created.

By default iTunes simply tries to transfer everything in your iTunes library onto your iPod, iPhone or iPad. This works well for many users, and is by far the simplest solution. In this mode, your iTunes music library and your device are essentially mirrored copies of each other, including all of your playlists from your iTunes library. Any new tracks you add to your iTunes library are added to your device the next time you sync, and any tracks you delete from your library are likewise removed from your device. Information on ratings, last played times, and play counts are transferred from the device back to your iTunes library, as is the saved playback position in any videos, audiobooks or podcasts you have partially played. 

If your music library is larger than the capacity of your device, iTunes will notify you of this and automatically select content to fill the available free space.


The Beginner’s Guide to iTunes

While this is a good way to quickly get some initial content onto your iPod, iTunes’ selections are often more random than anything else. This may be a good way to get up and running quickly, especially if your library is only a little bit larger than your device, but most users will probably prefer a bit more control over what content gets transferred.

Fortunately, you can easily choose what gets synchronized to your iPod or iOS device either by artist, album or genre or simply by creating playlists and telling iTunes to synchronize those playlists and their content onto your device. Once you’ve created a set of playlists, simply connect your device to your computer and select it from the Devices list on the left-hand side of your iTunes window. This will show you a Summary screen for your device with a list of buttons across the top of the screen showing the different types of content that you can synchronize with your device.


The Beginner’s Guide to iTunes

Simply select the Music button and you will be shown the options for automatically synchronizing your music content.


The Beginner’s Guide to iTunes

From here, you can choose to sync Selected playlists, artists, albums and genres and simply place a checkmark beside each playlist, artist, album or genre that you would like to synchronize with your device.

Note also the option to Automatically fill free space with songs. As the name implies, this option will automatically fill any remaining space on your device with a selection of tracks from your music library. In fact, when iTunes detects that your library is larger than the capacity of your device, it selects this option automatically with no further playlists, artists, or genres selected. You can refine this option further by selecting the specific items you want on your device and leave the Automatically fill free space… option enabled to keep any remaining space filled up with additional content.

Keep in mind that since this is a synchronization process, changing this setting will also remove any content that is no longer selected. So if you change your setting from Entire music library to Selected playlists, artists, albums and genres then content that is not included in any of those areas that you select is going to be removed from your device during the next synchronization.

With automatic synchronization, it is important to understand that you never actually manage the content directly on your device.