iTunes & drive recovery

Like many of you, I’m well aware of iTunes’ draconian policies regarding purchased content. However, I also knew from geekery that there had to be a way, and sure enough, while doing some random perusal at Best Buy, I saw software promising to move your iPod content back to your PC. Even better, when I got home and did some googling, I found this article on PlaylistMag.com explaining exactly how to get your iPod content off of your iPod and back onto your PC after a drive failure.

I installed my blank copy of iTunes and walked through the steps. At step 2 (or PC step 1b, depending on how you look at it), after plugging my iPod into the computer, iTunes 7.2 prompted me:

iTunes has found purchased content on your iPod which is not on your computer. Would you like to copy this content to your computer?

I’m like, SWEET! I don’t even have to go through these steps! So, I happily click for it to proceed with the copying and sit back. A sync begins. Then, I get this message:

Some of your purchased content could not be sync-ed to your iPod because it is not authorized to play on this computer.

It also had a link to go to authorize, so I authorized Happy. Then, I did a quick scan of my purchased content. All of it was showing as “file could not be found”. I looked at my iPod. Totally empty.

WTF. WTBF, even.

I’m pretty sure I grok what happened. It started copying content. Then, it realized I hadn’t authorized yet and stopped copying content because it wasn’t authorized. Then, it proceeded to do a normal sync (because that was the process that it had started to do in order to copy the content), at which point it removed all my stuff. But, one wonders why it prompted me to copy the content if it wasn’t actually going to copy the damn content!

I’ve written a strongly worded e-mail to iTunes technical support, and I’m prepared to call them if needed as well. I know I can’t expect much. Their DLA is very clear that it’s your responsibility to back up your purchased content. Nonetheless, I had a means to retrieve it until their software did this. So, we’ll see.