Since I’ve had an iPhone, there have been two occasions when I’ve purchased music via iTunes on my iPhone and have run into problems. In both cases, I decided / had to reformat my iPhone’s flash drive before I had synced purchased songs back to my main iTunes library.

Unlike iTunes Apps, which can be simply re-downloaded if they are accidentally deleted, songs in iTunes need to be backed up regularly because they can officially only be downloaded once. The most recent time this happened, I contacted Apple via a provided iTunes form on their website and asked for assistance. As I recall, I think I reported a problem with my purchase, and Apple support caused the songs in question to reappear in my download queue for my account. They wouldn’t download for some reason on my iPhone, but did on my laptop iTunes account.

DRM Revolution 01

While DRM and control-related issues like this with iTunes can be irritating, overall I still LOVE iTunes and am very pleased with my iPhone, Apple, their product support, etc. (I think the image above is humorous as well as thought provoking, but I am not sharing it because I have a big personal gripe with Apple.)

If you haven’t backed up your iTunes library lately, do it soon before you have some kind of hard drive problem. Last summer I burned a series of DVDs containing all of my iTunes Library at the time, and I now have those discs stored with family in another state. Hard drive failures can be traumatic, but at least I have pretty good confidence that I’d be able to recover the bulk of my iTunes library if something catastrophic would happen to my local copy. I’ve considered using a service like Mozy for offsite, “in the cloud” backups, but haven’t made that jump yet. I configured an Amazon S3 account last summer and was going to use Jungledisk for backups to it, but was deterred by how many hours the entire process was going to take. At some point I need to bite that bullet and just do it.

I started considering Mozy because I saw iJustine’s advertisement for it over the holidays on Hulu.

I guess this is personal verification that online marketing can change behavior… almost!

Mozy was not yet compatible with Mac OS 10.6 Snow Leopard when I looked at it in December, but it is now. Their “alternatives to Mozyhome” are pretty funny… and true.

Burn a new CD or DVD every Sunday night and store it at your brother-in-law’s office.
Pay $200/year for an online backup service that uses old, mediocre software.
Buy a $200 external hard drive and hope your office doesn’t burn down.
Do nothing and don’t worry about backup. (We suggest closing your eyes, plugging your ears and repeating “I’m in my happy place, I’m in my happy place.”)
Run a cron job of rsync, gzip and mcrypt piped over ssh to your friend’s server over his DSL line.

Are you using a backup service to backup your critical files offsite, “in the cloud?” If so, what are you using and what has your level of satisfaction been?

(If you are a vendor of a backup service or representative of one, please don’t insert your advertising links here… I am looking for consumer feedback.)

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5 Responses to Recovering lost iTunes Song Purchases (maybe) and iTunes Library Backups

  1. Barry says:

    I use Mozy to back up my home directory. That’s *in addition* to backing up to a Time Machine disk.

    The nice thing about both those is “set and forget.” Once Time Machine and Mozy are set up, they just purr along doing their things.

    But it’s not enough to have a backup plan. You also need a restore plan. What are you going to do *after* the inevitable happens? How long will it take you to be back up and running?

  2. Hey Wes,

    Thanks for another great article. This has happened to me several times on my iPhone, making me paranoid and fearful of that message that reads, “this will delete everything on your iphone, are you sure you want to do this?”, or something like that.

    Mozy sounds pretty cool, but switching services is tough (especially going from FREE to not free). I’ve been running (on Windows boxes) both Windows Live Sync, and Windows Live Mesh almost a year now (simultaneously side-by-side on the same boxes, 4 boxes)– since this blog entry:

    At around 13 or 14 Gigabytes, I kept hitting the 20,000 file limit on Mesh, but the actual total size limits published didn’t seem to be enforced. Sync is more generous with a maximum of 20 folders (or “libraries”), each with a max of 20,000 files and each file not to exceed 4GB.

    However, a few months ago, I began using Google Gbridge (also free), which is amazing thus far and far superior in a few key respects. It uses fewer resources (CPU, and RAM), and the built in VNC client is faster than windows Remote Desktop (possibly because of the VPN type). It’s not slick, and may be a tad confusing to some, but as I stated before, the performance is better, plus, there are some additional features that make sharing and granular security settings easy to access in the main console.

    AFAIK, Gbridge does not yet support Mac, although Skydrive, Sync and Mesh do.


  3. You can back up the songs on your home directory. However, from what I can judge (I’ve just gone through the experience of losing an iPod and getting a new MacBook) you will not be able to load the songs onto your iPod – it will reject them as “non-authorized”, forcing you to buy them again.

    There appears to be no way around this. It does not seem to apply to songs you did not buy through iTunes – everything I recorded or downloaded as MP3 (eg. from jamendo) copied fine.

  4. Wesley Fryer says:

    When you get that non-authorized message, in iTunes 9 you go to the “Store” menu and then “authorize computer.” You click on the song / songs you want to authorize – I am pretty sure you can do more than one at a time. This is part of Apple’s DRM. You shouldn’t have to buy them again in iTunes. This article from Apple gives more info.

  5. Haemon says:


    This is the best way to go about backups.

    Grab a copy of Acronis 10/11 Home (like 50.00) opt for the unviersal restore feature while your at it.

    Then go and buy a smaller version of the IOSafe (Waterproof and Fireproof) external hard drive enclosure….

    Backup your stuff locally, and stop wasting your time with slow CD/DVD burns and worrying if they are scratched or burned properly. If you take your backups serious, then try the above suggestions.

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