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Published July 15, 2006


How to Back Up Your iTunes Downloads and iPod Music Library

In a typical fiscal quarter, Apple Computer sells some 10 million iPods to consumers all over the world. Shoppers at Apple’s iTunes Music Store have bought more than a billion song downloads from the company. Clearly, there’s plenty of demand for buying music one song at a time over the Internet, downloading it, and then playing it on a portable device, instead of using traditional physical media such as CDs. But while strictly digital delivery is extremely convenient in a number of ways, it has a dark side: the files on your computer are not as safe as those on physical media. A typical hard drive lasts only three to five years, compared to the decades-long life spans consumers are used to with physical media. But there’s no reason you can’t keep your music library intact through several generations of computer and player hardware. To do that with Apple products, you’ll need to learn a few things about how the company designs them to manage downloads. That’s what we’ll take a look at here.

Many people are leery of purchasing music through sources such as iTunes because they’re understandably concerned about losing those purchases through the sorts of computer errors most of us have experienced plenty of. I bought a few songs through iTunes a while ago, and after an iTunes crash on my computer I discovered I couldn’t play them anymore. I gathered the information outlined below in researching how to get my files back, and how to keep from losing them again.

iPod disk mode

When you connect an iPod to a computer, it looks to the PC like a hard drive. Because Apple shields users from the low-level operating details of its various software, when you install iTunes it blocks viewing the iPod as a regular drive, and all access to your iPod can only happen through iTunes instead. This is a good move -- iTunes files are structured on an iPod such that you can’t use them as regular computer files without adding non-Apple software. The downside is that the only way to access the iPod is now through Apple’s iTunes interface, which works in only one direction. You can copy files to the iPod, but once they’re there, they don’t come back again: they can’t be copied from the iPod back onto your PC. The reasons for this are a mix of trying to make things simple and keeping iPods from becoming an easy way to transfer bootlegged music between computers, which helps Apple’s relationships with record labels.

To usefully back up the music files already stored on your iPod, you need to do two things. First, you need to get software that understands how files are stored on an iPod. The free Ephpod program was a great tool for this with older iPods that used the FireWire interface, but it can cause all sorts of problems with more recent models. A great list of currently available software that let you move files off an iPod is found at iLounge. They solidly recommend PodUtil, and there’s no need to duplicate here the tutorial they provide on its use. I often use XPlay, from Mediafour. Its integration with Windows Explorer lets me manipulate my iPod via batch files (an older way to move around files in Windows by typing commands) and similar means; very handy for those savvy with programming. XPlay also makes it possible for Windows PCs to transparently manipulate iPods formatted with the Mac OS.

The second thing to do is to turn on the ability to access the iPod as a regular disk drive, which Apple hides by default. PodUtil’s help file provides walkthroughs of the procedure in both Windows and Mac OS.

Computer backup considerations

Once you’ve copied everything from your iPod to your computer’s hard drive, you should save those files in a more permanent form. Right now, recordable DVDs are the best bet for most music libraries. New dual-layer DVD-R drives are inexpensive, and the prices of blank discs are reasonable, considering that each disc can hold up to 8.5GB. Dual-layer discs are considerably slower to copy to than their single-layer counterparts; if faster backup is a priority for you, you may discover that, counterintuitively, copying to single-layer, 4.7GB DVD-Rs takes less time overall.

For backup purposes, music libraries are pretty easy to separate into chunks of 4.7GB or 8.5GB each (minus a bit for overhead). You can just pick a range of letters of the alphabet and move all the music from artists whose names begin with those letters into a separate folder. For example, if you have a 20GB iPod, you could make folders for A-H, I-P, and R-Z, move artists into the proper sections, then make three backup discs. In Windows, to see how big each folder is, right-click on it and select Properties. Breaking up your library into pieces like this may take a little more manipulation within your operating system’s folder structure than you’re used to doing, but it’s a handy skill to hone: hard disks continue to dramatically grow in storage capacity faster than any permanent physical format now on the horizon.

As described below, if you’re managing everything with the iTunes Library interface, Apple has included software to let you back that up. You might find this approach easier than the one outlined in this section -- it supports incremental backups of just the new files you’ve changed, and automatically splits files onto multiple discs.

Working with iTunes downloads

When you download music from the iTunes Music Store, you can’t just do whatever you want with that music afterward. It’s important to understand the restrictions Apple’s Fairplay Digital Rights Management software enforces if you want to keep your music intact through the crises your computer will inevitably face in the future.

After buying a song, you get a window of time during which you’re allowed to download it from iTunes servers. If you lose the file, you can’t download it again later, so those making iTunes purchases need to make sure they’re backing up their music data properly. Apple offers suggestions at "How to back up your media in iTunes." The "Related Documents" section at the end tells you where the physical files are located on your hard drive if you want to save them by another means. It’s also possible to retrieve lost file downloads if they were copied to an iPod, though you’ll need to use third-party software, such as the PodUtil program described above. More hints on this topic can be found at Troubleshooting iTunes.

In addition to the physical file, Apple keeps a list on their servers of where you’re allowed to play that downloaded music file. You’re allowed to use each download on up to five different computers, which are then "authorized" to play that music. You can remove the capability to play by deauthorizing a computer, and once a year you can reset the authorized computer count on files that have reached the limit. Make sure to read Apple’s Authorization FAQ and "About iTunes Music Store Authorization and Deauthorization" to understand the procedures and limitations of this rights management system. Also be aware that some changes, such as reinstalling the operating system on your PC, can make that single computer take up multiple authorization slots; if possible, try to follow the deauthorization procedure before doing that.

Finally, if the authorization database on your computer (what’s called the "SC Info" file) becomes damaged, you can lose access to all of your downloads, and it’s not always possible to fix the problem from within the iTunes software. Check out the discussion threads about the infamous Error-208 for ideas about how to recover from this type of problem.

As with all digital-rights schemes, there’s always a risk that, in the future, Apple will decide or be forced to change the terms of their service to ones you aren’t happy with. So far, all such changes have increased consumer freedom by easing restrictions. The truly concerned can burn their downloaded music onto regular audio CDs to ensure that they’ll always be able to play it.

A happy ending

Back to the problem that kicked off my research. My copy of iTunes stopped working, but installing the latest version didn’t help; clearly, there was something wrong with my local file structure or database. To wipe that clean, I renamed the My Documents\My Music\iTunes folder, then reinstalled iTunes. That worked, but all my files were gone. Once I’d read "Where iTunes for Windows stores your audio files," I dove into the directory structure and found the music I’d purchased from Apple. I added just those files back to the music library, ignoring the rest of the corrupted structure in the old version. When I played the music, I had to authorize my computer again, and then everything was back to normal.

This procedure might be painful if you have a large downloaded music library, but it does work. Anything that does a complete backup of your My Documents folder in Windows (or your account’s home directory in Mac OS) should save all of these files. I confirmed that I could have retrieved them from my last backup onto DVD-R. No backup scheme is complete until you’ve tested it and know that you can recover your files following a disaster; I’ve now reached that comfort level with iTunes and its related store.

Computers are not as reliable as we’d like them to be, and the restrictions of Apple’s uneasy alliance with the record companies adds some unique twists to saving the music you download from their store. But once you understand how everything fits together, doing some basic backup and maintenance should keep your digital music safe for years to come.

...Greg Smith

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