One of the key announcements during Apple’s “Let’s Rock” event yesterday was the release of iTunes 9, another significant new update only a year after the debut of iTunes 8.

iTunes 9 once again changes the look and feel of iTunes in some subtle but significant ways, but more importantly finally provides some dramatically enhanced iPod and iPhone management and synchronization capabilities as well as the ability to more effectively share an iTunes library throughout a home computer network.
As always, there are a number of other changes buried under the hood and we take our usual more in-depth look at what changes iTunes 9 brings to the table and whether it truly is an improvement in terms of performance.
Downloading and Installing the Update
As usual, you can update iTunes either by downloading the new version directly from Apple’s web site at http://www.apple.com/itunes/download or simply choose the “Check for Updates” option in your existing version of iTunes.
The iTunes 9 download itself comes in at approximately 90MB for both Windows and Mac users. Quicktime 7.6.4 is also required for Windows users, but is bundled with the Windows iTunes 9 installer.
Initial Startup
During initial startup, iTunes 9 will take a few minutes to convert your existing iTunes library database to the new format required by iTunes 9. A typical iTunes user can expect this to take no more than 5-10 minutes, but if you have a large iTunes library, you will want to allow some time for this to run. Our largest iTunes library took over an hour for the conversion process to complete.
Further, it appears that even once this process has completed, quite a bit of background processing is still occurring in iTunes 9. For the first couple of hours, iTunes’ performance was mind-numbingly sluggish on our larger iTunes libraries, and even our smaller test libraries took a few minutes before the application became responsive. Our initial response, and yours as well, might be to conclude that iTunes 9 shows abysmal performance, but rest assured it gets quite a bit better once you allow it to do whatever it needs to do in the background. Again, typical users with smaller libraries may not even notice this particular issue.
With these database changes, you won’t be able to revert back to iTunes 8 after installing iTunes 9. iTunes does make a copy of your previous iTunes library prior to the conversion, but we’d strongly recommend doing the same yourself if you’re concerned about the possibility of downgrading.
New Look and Feel
iTunes 9 boasts an “improved look and feel” with some significant changes to the traditional media browsing layout. Most noticeable among this is that the browser is now a column on the left-hand side of the media library, as opposed to the traditional three-column view above your track listing.
Although Apple considers this to be an improved layout for browsing through your music library, we’re not convinced of this ourselves, and we suspect some long-time iTunes users may feel the same way. Fortunately, although iTunes 9 tries to force this new left-hand view on you by default, you can easily return to the traditional top-positioned column browser simply by selecting View, Column Browser, On Top.
iTunes 9 now allows you to choose which columns are shown in the Column Browser. In previous versions of iTunes, Artist and Album were always shown, and Genre was toggled under the iTunes preferences, and actually relegated to a hidden preference in iTunes 8.
With iTunes 9, the View, Column Browser menu option now allows you to choose to display not only the traditional Genre, Artist and Album columns, but also adds Composer and Groupings, which will be a particularly welcome addition for classical music fans. These columns are available in either the left-hand or on-top view.
While preserving the Grid views introduced with iTunes 8, iTunes 9 replaces the dark background used previously with a new white background.
Downloads Status
Another interesting change to the user interface is that downloads in progress now appear in the status panel as they did prior to iTunes 7, in addition to still being shown in a “Downloads” listing under the “Store” section.
Genius
Within the iTunes sidebar, “Genius” now gets its own category between Devices and Playlists. By default, this shows only the “Genius” section itself, which functions in the same way as it did in iTunes 8. The major change here seems to be that newly-created Genius playlists will appear in the “Genius” section by default, instead of appearing as normal playlists.
Genius playlists can be dragged from the Genius section down to the Playlists section, but they cannot be dragged back in the other direction. Any Genius playlists in your iTunes library will appear in the Genius section when collapsing the Playlists section, however.
Note also that Genius playlists now have a new icon that blends better with standard playlists and Smart Playlists.
iTunes Store Changes
Perhaps the most significant visual change in iTunes 9 is within the iTunes Store, which has been completely redesigned and is now almost unrecognizable from its former incarnation.
Other than a whole new layout, the most significant UI changes here are the use of a black menu bar at the very top of the screen to navigate through the different sections of the store. The menu bar includes all of the standard iTunes Store sections, with each item including a drop-down menu to navigate directly to a section.
The iTunes Store search has also been significantly revamped. Tracks in search results are now displayed in-line with the search results, rather than as a separate track listing below the main search results, and a set of filter options appears near the top-right corner to allow you to refine your search by media type.
Detailed song listings from search results are presented in a new listing format as well, again in the main single-pane view.
The “Buy” button that traditionally appears beside each item now includes a drop-down menu as well which can be used to select alternative options such as gifting the item, adding it to your wish list, copying the link, or sharing it on Facebook or Twitter.
You can also now view the iTunes Store using the full iTunes window. This is enabled on the Store tab in your iTunes preferences.
The Wish List replaces The Shopping Cart
The Wish List feature is new in iTunes 9 and essentially replaces the Shopping Cart found in previous versions, although users who were fans of the Shopping Cart feature will likely find the Wish List feature to be disappointing by comparison. Firstly, the Wish List appears within the iTunes Store, rather than as a separate item in your iTunes Source list, making it more difficult to find. Where the Shopping Cart was always displayed, your Wish List is accessed by clicking on the drop-down menu arrow beside your iTunes Store account name.
More significantly, however, when using the “Shopping Cart” iTunes would add new items that you purchased to the shopping cart rather than purchasing them immediately. Essentially, all of the “Buy” buttons in the iTunes Store became “Add” buttons, and nothing was ever purchased until you actually visited your shopping cart and “checked out.” With iTunes 9, one-click purchasing is enabled by default everywhere, and adding items to the Wish List requires an extra click to bring up the pull down menu and select the “Add to Wish List” option.
Note that shopping cart users will receive a warning from iTunes 9 about this after they upgrade from iTunes 8.
The Wish List does have the advantage of being stored within your iTunes Store account and therefore available from anywhere, but beyond that it’s hard to see how the loss of the Shopping Cart is really an improvement in iTunes, particularly for those users who want to control their spending on iTunes.
Future improvements in the Wish List, such as the ability to publish it for gift purposes like you can on Amazon, may make the feature considerably more useful, but the Wish List is still not a viable replacement for the Shopping Cart in our opinion.
Facebook and Twitter Integration
The Facebook and Twitter options merely open a web page to the selected service within your default web browser with the appropriate information already filled in.
Links to most items found on the iTunes Store can be shared via Facebook or Twitter, but in reality this amounts to little more than viral marketing on the part of the iTunes Store.
iTunes LP
The iTunes Store now includes extra content with select iTunes albums such as liner notes, lyrics, performance videos, photos and more.
The “iTunes LP” format is a proprietary format used by iTunes and currently can only be viewed through the iTunes application itself—it is not available on the iPod, iPhone, or Apple TV, although the music tracks themselves can be synced in the same manner as any other music track.
Note that the “iTunes LP” feature is only available on the “Deluxe” re-released versions of albums. At this time Apple is not offering any kind of upgrade path for customers who may have already purchased the non-iTunes-LP version of the album. Basically, if you want the extra content you will be forced to re-purchase the entire album.
iTunes Extras
Similar to the iTunes LP feature, iTunes Extras provide additional content for certain movies purchased from the iTunes Store. Essentially, the “iTunes Extras” feature include the extras that would be found on a typical DVD purchase of the same movie.
The iTunes Extras are downloaded and stored as a separate file, generally prefixed with the name “iTunes Extras” in front of the movie name. This is currently a somewhat counter-intuitive approach, as most users would assume that the iTunes Extras would be stored alongside the movie, and perhaps even that iTunes would offer the option of viewing the extras when starting the movie, in the same way traditional DVDs work.
It’s also worth noting that iTunes Extras can presently only be viewed in iTunes itself; they are not compatible with the iPhone, iPod or Apple TV. This significantly limits their usefulness as a DVD replacement, although we hope to see an Apple TV update to add iTunes Extra support in the near future.
Note that iTunes Extras are only available on purchased versions of movies. Rentals do not include any iTunes Extra content.
Further, as with “iTunes LP” users who may have previously purchased a movie that now has “iTunes Extras” available will need to repurchase the movie again to get the extra features. Apple is not offering any kind of upgrade path for existing customers at this time, and based on past history it’s not likely that they will do so.
iTunes Plus Upgrades
The option for iTunes Plus upgrades appear to have disappeared completely from the iTunes Store. While iTunes 8 still provides this option in the older iTunes Store layout, it does not appear anywhere in iTunes 9. It is unclear whether this is simply an oversight on Apple’s part or an indication that they plan to discontinue the iTunes Plus upgrade program.
iTunes U Section
iTunes 9 now separates iTunes U downloads into their own section. In previous versions of iTunes, these appeared either as subscribed podcasts or individual items within the normal iTunes library.
Note that previously-downloaded iTunes U content will not appear in this section, but will remain in the Podcasts or general library section as before. To make them appear in iTunes U they must be re-downloaded.
Home Sharing
iTunes 9 now finally provides a slightly more streamlined way to share content between multiple computers in your home. Although iTunes has provided library sharing features for quite some time, your shared iTunes library was limited to listening only on other computers, providing no ability to transfer tracks between computers or sync them to portable devices that you might have connected to those computers.
With iTunes 9 you can now enable the Home Sharing feature to permit you to easily share your content between multiple computers in your household. When you first run iTunes 9, the “Home Sharing” feature will appear in your iTunes source list in the “Sharing” section. Selecting it will take you through the process of setting up Home Sharing.
You will need to enter your iTunes Store account name and password to enable Home Sharing, as this is used to link your shared computers together. Home sharing only works between computers that have been configured to share using the same iTunes Store account. Note that the account used for Home Sharing does not necessarily need to correspond to the account used to purchase your iTunes Store content, although your computers will need to be authorized to play any content purchased with other iTunes Store accounts.
Once enabled between two or more computers, Home Shared libraries will appear in the “Shared” section of your iTunes source list with a small house icon beside them to distinguish them from traditional shared libraries:
Selecting the shared library will allow you to access all of the content in that particular library. From here you can either listen to the content directly as you would with any other shared library or copy it to your own iTunes library by dragging it from the shared library and dropping it onto your main library at the top of the iTunes source list, or selecting it and clicking the “Import” button in the bottom-right corner of the iTunes window.
In addition, you can filter the shared library view to only list items that are not already in your current library by selecting “Items not in my library” from the Show drop-down menu at the bottom of the shared items screen.
The Home Sharing feature also provides the ability to automatically copy certain types of items between iTunes libraries. This feature is accessed by clicking on the “Settings” button near the bottom-right corner of the iTunes window:
Note that this is the closest that the Home Sharing feature comes to a true “sync” operation. The copy operations are one-way and are simply used to match up library content – other metadata such as ratings, playlists, play counts, and track information is not replicated between libraries, and files are not automatically re-copied if changed.
Also note that Home Sharing appears to offer no specific advantage for iPod synchronization. Content from a shared computer cannot be synced to an iPod or even added manually—it must first be imported to the local iTunes library and then synced to the iPod as it would normally.
Genius Mixes
iTunes 9 provides a new “Genius” feature that now automatically builds up to twelve mixes of songs that go play well together, intended for continuous DJ-style playback.
The Genius Mixes option will not appear in the source list until iTunes has actually generated the Genius Mixes, which requires updating your iTunes Genius database by selecting Store, Update Genius from the iTunes menu. Note that the number of Genius Mixes generated will depend on the size of your library and how much compatible music is available. On very small libraries or medium-sized libraries with very diverse content, the Genius Mixes may not appear at all, or may provide only one or two mixes instead of the full twelve.
Once the Genius data has been updated, the “Genius Mixes” option should appear in the “Genius” section of the iTunes source list. Selecting this option will present a grid of Genius mixes, with a mosaic of four pieces of album artwork in each one. Each mix is given a descriptive name based on the genre from which its music is drawn as well as a list of artists that the mix is primarily based on. You can play any of the mixes simply by clicking on the icon—the artwork will change to reflect the currently playing song and the mix begins playing.
Note also that we had some difficulty getting this option to appear even in our largest iTunes libraries despite updating the Genius data several times. We suspect this may be a bug in the feature or might be simply the result of high traffic on the iTunes Store servers. The option finally appeared in our largest library with a full twelve mixes, and in a smaller library with only six Genius Mixes.
Once generated, you can also sync your Genius Mixes to your iPhone or iPod touch or 5G iPod nano by selecting them from the “Music” sync tab.
Once a Genius Mix has been synced to your iPhone or iPod touch, a “Genius” option will automatically appear on the left-hand side of the menu bar to allow you to view and play your Genius Mixes on your device. Each mix is shown on its own “page” and you can swipe left and right to navigate between the various mixes.
Note that there appears to be no way to actually get a list of songs in a Genius Mix, nor even a way to rate songs or add them to another playlist while listening to a mix—an unfortunate limitation in terms of discovering new music, since this makes it difficult to flag songs for later listening. About the only way to do so is to click the “Genius” icon while a song is playing, which will generate a standard Genius play queue based on the currently playing track, however this also aborts the Genius Mix in favor of the new Genius play queue.
Genius Support in iTunes DJ
The “iTunes DJ” feature can now draw tracks from the normal “Genius” section.
When “Genius” is selected as the source, the iTunes DJ feature will draw tracks dynamically from the iTunes Genius feature, rather than from a static playlist.
Improved Smart Playlist Rules
iTunes 9 finally introduces support for considerably more complex Smart Playlists. In previous versions of iTunes, a Smart Playlist could only be built to either match ALL of the listed criteria or any one of several listed criteria. This meant that you could build a Smart Playlist that selected all music from your “Rock” genre that had never been played, but if you wanted to build a Smart Playlist that selected all Rock and Jazz music that had never been played, you were out of luck. Power users overcame this in the past by building nested playlists for multiple levels of criteria. In iTunes 8 and prior, you would have had to build one Smart Playlist that included all tracks in either the “Rock” or “Jazz” genre, and then build a second Smart Playlist that included tracks from the first Smart Playlist with a Play Count of zero:
With iTunes 9, it is now possible to have multiple levels of Smart Playlist criteria in order to build these more complicated scenarios without relying on intermediate playlists. For instance, a Smart Playlist for the previous scenario in iTunes 9 would look like the following:
Criteria can now be nested up to five levels deep, allowing some very complex Smart Playlists to be created with iTunes 9.
Further, iTunes 9 adds a couple of additional Smart Playlist criteria. “Purchased” can be used to determine whether an item was purchased from the iTunes Store or not, making it much easier to include this content in a Smart Playlist. “Media Kind” is now available as well to test for the field first introduced in iTunes 8, and allows Smart Playlists to be built based on the various media types available in iTunes. With the addition of the “Media Kind” criteria, the “Podcast” and “Video Kind” criteria are irrelevant and have been removed.
iPhone and iPod touch Home Screen Management
iTunes 9 and iPhone OS 3.1 now provide the ability to manage your iPhone or iPod touch home screen layout right from within iTunes itself. This is done directly from the “Applications” tab for the device, which has now been moved further to the left and provides a revamped layout for application management on your devices:
A list of applications stored in your iTunes library is shown on the left, with additional information shown beside each one, such as category and size of each. The list of applications can now be sorted by Name, Category or Date, and a search field is provided to help you locate a specific application.
Apps can be installed either by checking them off as you normally would, or by dragging and dropping them to a home screen page on the right. This installs the application and determines where it appears on the iPhone home screen.
Applications can be re-organized on the home screen simply by dragging and dropping them to new positions. Thumbnails of each home screen page are shown on the right, and applications can be moved to other pages by dragging and dropping them to those pages, or dragging them to the grey blank page at the bottom to create a new page. Dragging and application icon over an existing page and holding it there will also switch to that page and you can then position the icon in a specific location on that page.
The application pages themselves can also be reorganized by dragging them up or down in the list to change their order.
To remove applications, you can either UNcheck them in the application list on the left or hover over them on the home screen and click the X which appears, in a manner similar to deleting them directly on the device itself. Note that built-in applications still cannot be removed or hidden. Further, even web-clip icons, which can be deleted on the device itself, cannot be deleted from within iTunes.
Note that you must also be running iPhone OS 3.1 on your device to be able to manipulate the home screens from within iTunes. Older iPhone OS versions will show the application list without the home screen management panel.
iPod and iPhone Syncing
One of the other biggest enhancements in iTunes 9 is a greatly improved set of synchronization options for your iPod and iPhone. Most of the iPod and iPhone synchronization options have been completely re-designed to provide significantly more flexibility. Note that although the Apple TV sync screens inherit these cosmetic design changes in iTunes 9, the expanded sync options are not yet available for Apple TV devices, and syncing the Apple TV behaves as it did in iTunes 8.
Music
In previous versions of iTunes, you could choose to sync either your entire music library or only selected playlists. iTunes 9 expands upon this by allowing you to also select entire artists or genres to be synced in addition to your playlist settings. This is shown by three separate lists on the “Music” sync tab.
Options can be selected from all three of these lists, and all of the selected content will be synchronized to your device. The Artists list also includes a search field to help you quickly find a specific artist.
The Music tab also now includes an option to “Automatically fill free space with songs” which will fill up any available space on your iPod or iPhone with additional music content. This is similar in concept to the Autofill option introduced in iTunes 8.2, but works automatically during each sync and still allows other automatic synchronization options to be used.
Movies
The Movies sync settings page now shows a more detailed grid-view of available movies in your iTunes library with additional information such as movie artwork duration, size and rating. As with the Music and Applications tabs, a search box is available to search for specific movies b. name.
You can now choose to sync movies by individual movie title and playlist or choose to automatically include all movies or recent movies. Note that the playlist box is only shown if you actually have playlists containing movies in your iTunes library.
TV Shows
The TV Shows tab has been similarly redesigned with much more flexibility for syncing TV Show content to your devices. This screen now shows artwork for each TV Show in the listing of TV shows, but also provides an additional column to select individual episodes of a selected TV show, allowing you to sync specific episodes without resorting to creating playlists.
Episodes are further organized in this listing by season, making it easy to select entire seasons. The automatic selection options are still available as well, and will automatically select based on criteria such as “Unwatched” episodes while still allowing you to sync additional episodes individually.
Syncing by playlist is also supported in addition to the other options, and as with the Music screen, you can choose a hybrid sync of both shows/episodes and playlists. Note that the playlists option is only shown if you actually have playlists containing TV Shows in your iTunes library.
Podcasts
The Podcasts tab has been changed to work in much the same way as the TV Shows settings. You can sync by podcast, by episode, and by playlist, with automatic selection of all, unwatched, or recent episodes. As with Movies and TV Shows, the Playlists section only appears if you actually have playlists containing Podcast episodes.
iTunes U
To accompany the addition of an “iTunes U” section in the main iTunes library, iTunes U content also now gets its own sync settings screen.
These settings work in the same manner as Podcast settings.
Photos
For iPhoto users, the Photos sync settings now provides the ability to sync individual Events and Faces from your iPhoto library in addition to albums.
Recent events can also be included automatically, and any included events are auto-selected in the Events listing. Additional events can still be selected, however.
iTunes 9 also now provides the ability to sync videos into the albums on iPhone and iPod touch devices running OS 3.1. The “Include Videos” checkbox will include any videos stored in the selected iPhoto items, if syncing from iPhoto, or the selected folders if choosing to sync from a folder on your computer. Note that only iPhone-compatible videos will be synchronized. iTunes does not provide any conversion for incompatible video formats.
One negative change in the Photos sync settings is that you can no longer customize the order in which albums appear on your device. iTunes previously allowed you to customize the order of albums on your device by dragging them up or down to change the order – a feature that has been available since the first iPod photo was released with iTunes 4.7. Sadly, this option is no longer available in iTunes 9, and photo albums will be synced to your device in the order they appear in iPhoto itself, or alphabetically in the case of syncing by folder.
iPod Games
The “Games” tab for older click-wheel models has undergone a similar transformation to the Applications tab. Home screen management is obviously not available here, but the layout of iPod Games is presented in a similar fashion to the Application tab, with sorting options by Name, Size and Date, icons presented for each game, and a search field to locate a specific game.
iTunes Media Organization
Although video content was introduced to iTunes several years ago, the layout of the iTunes media content on your hard drive has long reflected iTunes’ roots as a music-centric player, with most music stored at the top-level folder, and Movies and TV Shows stored in sub-folders almost as if they were an afterthought.
iTunes 9 now organizes your content into a “Media Folder” structure, with sub-folders for each media content type: Audiobooks, iTunes U, Movies, Music, Podcasts, Ringtones, TV Shows and Voice Memos.
These folders are also organized into further sub-folders. TV Shows are now organized by show and then grouped into sub-folders by season underneath each show. Movies are places in their own individual folders, likely to account for support for new “iTunes Extra” content that may be downloaded alongside the actual movie.
If you’re starting a new iTunes library, this will be the folder structure by default. However, if you’re upgrading from a previous version of iTunes, the previous folder structure is maintained and supported for the sake of backward compatibility with any other applications that may expect iTunes to organize your files in a certain way. You can switch to the new structure at any time, however, simply by visiting the File, Library, Organize Library menu option in iTunes. This will present a dialog box with the option to upgrade your library to the new iTunes Media organization.
Note that for advanced users with large libraries, this can also be a great opportunity to weed out content that may be living in your iTunes Music folder that isn’t actually referenced by iTunes. When the upgrade to the new folder structure is complete, any artist-specific folders that remain directly under the main iTunes Media folder will contain content that isn’t listed in iTunes itself.
To perform the upgrade, simply check this option and click OK. The upgrade process is surprisingly fast, since files are simply being moved to new locations—a 50,000 item library took about 3-4 minutes to reorganize.
Automatically Add Content to iTunes from a Folder
With this new folder structure comes another feature that many iTunes users have been requesting for a very long time: A “watched” folder for automatically importing content into iTunes.
After you have converted your iTunes library to the new structure, an additional folder is created labelled “Automatically Add to iTunes.” As the name of this folder implies, anything placed into it is automatically imported into your iTunes library.
Consolidate Library
The Consolidate Library option has now been moved to the “Organize Library” dialog box, however it behaves in the same manner as before—it will copy any tracks that exist outside of your iTunes Media folder into the iTunes folder structure.
New in iTunes 9, however, is the option to consolidate only selected tracks rather than your entire library. To perform a consolidate operation on selected tracks only, simply highlight the tracks you would like the consolidate, right-click and choose “Consolidate.” iTunes will prompt you to confirm that you want to copy these tracks into your iTunes Media folder.
What still hasn’t changed – iPhone Manual Mode
The inability to manually manage the media content on an iPhone from more than one computer continues to be a source of frustration for many of our readers, and unfortunately it appears that iTunes 9 and iPhone OS 3.1 continue to lack this capability. We’ve come to conclude that this is either a deliberate design decision on Apple’s part, or an omission that they simply don’t care enough about fixing, but had hoped that with all of the new synchronization capabilities in iTunes 9 that this may have finally been addressed.
Sadly, this is not the case, and the inability to manage media content from more than one iTunes computer remains one of the oddest limitations we’ve found and for many users is enough to keep the iPhone from truly being usable as an iPod.
Performance
Other than the issues noted at the beginning of this article with upgrading existing large iTunes libraries, the performance of iTunes 9 seems to have changed little from iTunes 8. iTunes 9 is not noticeably faster than iTunes 8 overall, although some aspects such as searching and browsing for music seem to perform better than they did in the past, suggesting an optimized database. Note as well that even the Mac version remains a 32-bit application, not optimized for Snow Leopard.
From a stability point of view, iTunes 9 might actually be less stable than previous versions. During our testing for this article, iTunes 9 Mac crashed completely on us at least three times while performing what should have been routine operations—changing iPod sync settings, accessing the iTunes Store, and playing music. Considering that we can’t remember the last time we saw iTunes crash on the Mac, this does not bode well for the stability of iTunes 9. iTunes for Windows also crashed at least once, although it should be noted that our use of the Windows version was far less extensive than the Mac version. Again, however, these crashes occurred on computers and iTunes libraries that have had absolutely NO issues with previous versions of iTunes going back to the 7.x versions.
Update or wait?
iTunes 9 offers a few nice new features, although most of these seem centred around the iTunes Store itself. What other features it offers are definitely targeted at more advanced users: Users with larger libraries or more than one iTunes computer at home, or those with more advanced syncing requirements for iPod and iPhone devices, or a lot of iPhone or iPod touch applications to manage.
Further, new iTunes Store features such as iTunes LP and iTunes Extras pretty much require iTunes 9, as likely will the new iPod models released yesterday.
For the average iTunes user, however, there may be little need to bother with updating to iTunes 9 right away, as iTunes 8 will continue to work fine, even with the iTunes Store, which will continue to be presented with the older interface. The stability that we’ve seen in iTunes 9 thus far certainly gives us pause in terms of recommending that users rush out and upgrade right away.