Apple's tight control over the iTunes/iPod/iPhone ecosystem has a lot of benefits, yet it also means that you're forced to play by Apple's rules--some of which may be a little too restrictive for your tastes. Take, for example, the inability to copy songs back from your iPod to your computer.
Even though iTunes has a manual mode in which you can copy songs willy-nilly onto an iPod from an iTunes library (or multiple libraries), it does not allow you to perform the same procedure in reverse. And if you lose all of the music on your computer in a giant crash, say, it would be really useful to be able to recover what's stored on your iPod.
That missing piece of the puzzle is available, however, supplied by a host of third-party developers who've made applications that perform the task of copying back songs from any iPod onto any computer. Here's a look at ten such apps--ranging from the feature-laden do-it-alls to the bare-bones minimalists, the paid to the free, and everything in between--to help you decide which one(s) should be in your arsenal.
(To prevent iTunes from trying to auto-sync when you connect your iPod, remember that you can hold down the Command and Option keys while you plug in the iPod to do so).
Fitting squarely in the bare-bones category, Steve Joynt's free Expod immediately detects any connected iPod upon launch and lists it in the sidebar on the left. Click your iPod and you're presented with a list of all the tracks it contains. You can then either manually select the songs you'd like to copy (aided by a search box) or press Command-A to select them all. When you click the Extract button--the only one in the toolbar--the next window lets you specify a destination for the files to be copied to and gives you the option to have them filed in folders based on the metadata information contained within them. Although Expod shows the playlists on your iPod, it can't copy them, and the app doesn't copy files directly into iTunes.
Findley Designs's $20 iPod Access has most of the features you'd expect--it quickly detects any iPod you connect, it allows you to browse and search songs, it supports videos, and can effortlessly import songs from your iPod into any folder on your Mac or straight into iTunes (even making sure that it does not let in any duplicates). It also lets you import all the playlists on your iPod into iTunes with the click of a button. So what doesn't it do? For starters, it does not let you play the songs on your iPod directly from its interface. But I have a more serious gripe: the user interface is dated and does not really belong in the Leopard era. If you can get over that, however, it's definitely a capable app that will get the job done.
The Little App Factory's $20 iRip (previously known as iPodRip) has a simple interface and a few nice features. Beyond the normal abilities to search for and copy selected songs over to your Mac, iRip gives you the ability to import those songs into iTunes and even copies over the playlists from your iPod. Upon first launch, it presents a screen that gives you the option to choose between Automatic Recovery mode--which copies over all the media, along with the playlists, from your iPod onto your Mac--and Manual Import mode. The latter, however, does not let you play the songs on your iPod or browse through them by specific metadata. It also makes no distinction between songs you already have in your iTunes library and the ones you don't have, instead making duplicates of the former if they happen to be in the selection you chose to import. When you change iPods while iRip is running, it doesn't refresh the contents automatically either, forcing you to do it manually by closing the window and choosing the currently connected iPod on the screen that pops up.
Marcus Mueller's free iTunesFS takes a different approach from the other apps looked at here. In fact, it's not really an app at all--it's a FUSE-based file system that requires that you first install MacFUSE. When you plug in an iPod (iTunesFS doesn't support the iPhone or iPod touch) and double click the app, you'll see an iTunesFS volume mount on your desktop. Open it and you'll see your connected iPod as well as well as an iTunes folder. Open the iPod folder and you'll see folders such as Albums, Artists, and Playlists. From there you can drag a file or folder to your desktop, or directly into iTunes, to copy it to your Mac. It doesn't prevent you from creating duplicates of items already in your iTunes library, and the only way to 'recover' playlists is to drag a playlist folder into the Playlists area of iTunes' sidebar, but it does give you free access to the contents of your iPod.
Of all the applications vying for the top spot, KennettNet Software's
Pod to Mac
Pod to Mac used to be free for Mac users, but now costs $20 (although an introductory price of $10 was available when this review was published; and you can still download an older version to use for free). Even though the design has improved with the paid version, the user interface is still sloppily put together and feels very alien on the Mac. However, it also happens to be quite full-featured. Not only does it let you select the tracks you want and copy them to the desktop (which is the only location it will copy to besides a predefined subfolder in your Documents folder), it will also copy them into iTunes for you. What's more, the Automatic Transfer button in the bottom-right corner copies only those tracks from the iPod that do not exist in your iTunes library, ensuring that you do not end up with duplicates. The app doesn't have any sorting or browsing features but it does let you search for and play the songs on the iPod from within its interface. It is also supposed to allow transferring of photos from most iPods, but it did not work with my iPhone. It is clear that the paid version of Pod to Mac is suffering from teething issues and I wouldn't recommend purchasing it until they have been sorted out.
Sci-Fi Hi-Fi's PodWorks has the potential to be a strong contender, what with its low price and a seemingly well-rounded set of features, but it doesn't deliver on several of its promises. The interface itself belongs to the pre-Leopard era and still has those buttons that once used to be Brushed Metal before Apple decided to eliminate it from Mac OS X. The features are plentiful--it boasts of being able to detect all varieties of iPods and import songs into iTunes or to folders on your Mac, taking care to weed out the duplicates. It also has support for playback of songs and recreation of playlists. However, the playlist support is extremely buggy and I always ended up with multiple copies of the same song in the playlists created by PodWorks. Also, although it has menu-based options for playing back music and controlling volume, none of those ever actually worked in my testing.
Like Music Rescue, FadingRed's Senuti (yes, that's iTunes backwards) has most of the features you'd be looking for--searching and sorting of tracks, status icons to show which tracks are already in iTunes, copying of tracks either to iTunes or any folder on your Mac, the ability to play songs from within the interface, playlist support, and the ability to copy videos. All of those features work exactly as advertised and, for the most part, you'll be able to get around the interface intuitively enough. There are a few omissions though--dragging songs out of the interface and onto the desktop does not work, unlike most other applications, and you have to drag playlists into iTunes' source list for Senuti to recreate them on your Mac. Furthermore, it does not have a browse feature or one-click automatic recovery, and the interface design leaves something to be desired.
Wide Angle Software's TouchCopy does everything you could possibly expect it to and then some. However, like a lot of cross-platform, Java-based applications, it crams all that functionality into a poorly designed interface with a startling lack of attention to detail (for example, it refers to your Mac as a PC on one of the screens). Besides having every single feature mentioned in this article so far, it can also transfer photos from your iPod and use it as a USB storage device. It can do automatic recovery, recreate playlists, lets you search and play songs, can show you just the songs that aren't there in your iTunes library--the works. However, it has two major flaws--the significant amount of time it takes to generate the list of items on your iPod (specially when it is first launched) and the completely alien user interface.
DigiDNA's TuneAid has all the makings of a great application but falls short when it comes to user interface design. It allows you to search and sort your tracks, browse through them by metadata, and play them back while you decide which ones you want to import. It has full support for playlists and can recreate them in iTunes exactly as they appear on your iPod. The importing worked flawlessly in my testing and it even took care not to make a second copy of songs that already existed in my library while importing (though the feature isn't enabled by default). You can also import songs to a folder on your Mac if you so wish. About the only thing that's missing is the delicious-looking UI that has been the hallmark of many a great Mac app.
Macworld's buying advice
Most of the apps have pretty much the same features and all of them ably perform the most basic task of getting your music off your iPod and onto your Mac. If you have somehow lost the iTunes library on your Mac and want to make an exact copy of the library as it exists on your iPod, you'll do just fine with downloading the discontinued free version of Pod to Mac. It will not rescue your podcasts or audiobooks and does not exactly have a stellar user interface but it will perform the most elementary tasks without costing you a penny.
If you don't mind shelling some money for a more advanced and well-designed application, however, I recommend you give KennettNet's Music Rescue a try. Among all the apps I looked at, Music Rescue has the best blend of features, design, and price, and should be a fitting companion for your iPod and iTunes library.
[Aayush Arya is a regular Macworld blogger living in India. Macworld senior editor Jonathan Seff contributed to this roundup.]
This story, "IPod Extraction Tools" was originally published by Macworld.