Dear Steve: you missed a spot

Why is it so difficult to transfer an iTunes library using your iPod when you buy a new Apple Mac computer?

Molly Wood Former Executive Editor
Molly Wood was an executive editor at CNET, author of the Molly Rants blog, and host of the tech show, Always On. When she's not enraging fanboys of all stripes, she can be found offering tech opinions on CBS and elsewhere, and offering opinions on everything else to anyone who will listen.
Molly Wood
3 min read

It wasn't so long ago that Steve Jobs shocked us all with his Thoughts on Music memo, in which he derided digital rights management restrictions as anticonsumer and said Apple would embrace the abolishment of DRM "in a heartbeat." He said DRM had done nothing to stop rampant music piracy, and that users would embrace options that respected their fair use rights and let them use any device and any computer to listen to their music. Remember that? What a day. It led to a landmark deal with EMI to sell DRM-free songs on iTunes and frankly, returned some dignity to consumers who are sick and tired of being treated like pirates and abused by ridiculous content restrictions at every turn.

So, that leads me to this question. Why is it that I still can't just drag my legally obtained songs off my iPod onto, say, my work computer in order to maintain separate iTunes libraries on multiple computers? Instead, I have to load up the iPod, stop it from auto-syncing with iTunes and overwriting my iPod completely, enable hidden folders, find those hidden folders, copy them to my computer as a series of unnamed files, and then wait for iTunes to rebuild the song names; and heaven forbid I drag the songs to the Library and then forget to tell iTunes to also copy the songs to the iTunes Music folder, or else it'll all be undone when I unplug the iPod.

Why is it that if I buy a new computer and I want to transfer my iTunes library onto it, I have to go through all of these shenanigans, which involve configuring your iPod as an external storage device instead of a magically-syncing music player, instead of just syncing my library like normal, plugging my iPod into my new computer, and reverse-syncing it lickety-split?

Why is it that if I want to transfer my iTunes library from a PC to a Mac, I have to treat it like a giant file-transfer--either wiring the two machines together, transferring over a wireless home network, or, again, employing some complex tomfoolery involving the configuring the iPod as a storage device (which it is) and not a syncing music player (which it also is) and then the multiple reformats that shouldn't be necessary if it's just a storage device (which it is)? I actually had to go over to a friend's house this weekend to help him move his wife's music off their PC and onto her new MacBook. If the Apple experience is supposed to "just work," such a visit should never be necessary.

The iPod has always been a one-way sync device. It's always been too hard to maintain separate iTunes libraries (between multiple computers or multiple users), and the root cause is antipiracy. I get that. But it leads to a very un-Apple experience, and it's especially silly since one of the goals of the iPod is to entice users off their Windows machines and onto Macs. Why not make putting your iTunes library on that new Mac as easy an experience as it was to put the music on the iPod in the first place?

The time has come for the new, evolved, pro-fair-use Steve Jobs to treat the iPod like the universal mass storage device that it is. Let me copy some music to my work machine and leave the rest at home. Let me load up my iTunes library from a PC, take it over to a brand-new Mac, and drag and drop with impunity. And if you fear that to allow such behavior would jeopardize your relationship with the studios (who are already kind of peeved at you over the whole anti-DRM stance and refusing-variable-pricing thing anyway, so what do you care, but I digress), then why can't some Apple engineer just write a simple piece of software that would accomplish this task in an equally simple fashion? It could even do disk-spanning if your library is bigger than your iPod! Multiple trips is still better than a multi-day file transfer. Anyway, I'm sure it's just been overlooked in all the iPhone hubbub and such, so I thought I'd just point it out. You're welcome. I'll be waiting!