I bought a 3rd generation iPod Touch awhile ago and have been an enthusiastic supporter of Apple’s various music players ever since.  I had owned another brand of mp3 player previously but when I made the switch to the iPod, I gained the convenience of the iTunes store.  I think that is one of the main reasons that Apple has maintained their lead in this crowded market.  I spent a few months on a conversion project, ripping all of my CDs so that my iTunes library now contains all of my music.  I subscribe to several podcasts.  I have created a bunch of playlists.  I have purchased a bunch of music and applications from iTunes.  I love my iPod and use it all the time, for all kinds of things.

I just got a new laptop.  And here’s where I have encountered my first annoyance with the way that iTunes works.  What I would have liked to do is simple.  I wanted to install iTunes on my new laptop, plug my iPod into the new laptop and have my entire library downloaded from the iPod to the new laptop via iTunes sync function.  Sounds simple and seems intuitive that that’s the way iTunes would work.   To my surprise, I discovered that this is NOT the way iTunes works.

I downloaded iTunes onto the new laptop without incident.  I authorized my new computer to access my iTunes library and discovered that each library can have as many as five computers authorized to use it at any given moment.  Not a problem since I only have two.  I made sure that my new, blank iTunes library would not overwrite the library on my iPod and started the sync process.  When it was complete, I noticed that hardly any of my music had been transferred and none of my playlists, applications or podcasts had been transferred.  When I looked more closely, I realized the only things that had been transferred were the songs that I had purchased from the iTunes store.  None of the music I had ripped from my CDs had been transferred to the new laptop.  Thinking I had done something wrong, I checked all of the options and settings available and tried syncing again.  No additional items were transferred.

I then searched for a solution and was shocked to discover that what I wanted to do is something that is not easy to do.  The best article I read on the topic is a bit arcane but the gist of it is that Apple has decided that the relationship between your iPod Touch and your computer is primarily a one-way relationship.  It’s easy to get media files from your computer to your iPod but much more difficult to get media files from your iPod to your computer.  The only exception to that “rule” is a media file that you purchased from the iTunes store.

One theory about why Apple has made this non-user-centered choice is that they are trying to appease their corporate partners concerning copyright issues.  That may be the reason but why then would they have made it easy to transfer your iTunes store purchases?  In any case, this should not be as difficult as it is proving to be.  One of the things I tried was to use the iTunes software to make a backup of my library on my external hard drive and then import that backup to my library on my new computer.  But when I tried this option within the software, it would only let me make a backup to a CD or DVD.  I could not choose where I wanted to store that backup–it had to be stored on a disk in my DVD drive.  This would require many, many CDs or DVDs and so I think people are unlikely to really choose this option for backing up their libraries.

My latest attempt (one that I am in the middle of) is to go outside of the iTunes software to use Windows to copy the iTunes folder from my old C: drive to my external drive and then from my external drive to my new computer’s C: drive.  I fear this might not work because of a number of issues that I’ve read about.  If it doesn’t, the articles that I’ve read suggest that I should purchase one of several pieces of software that have been written by third party vendors to help out people in my situation. 

I am very annoyed with Apple at the moment.  This task is a common, reasonable task to want to accomplish.  The choice that they have made here does little to thwart piracy but instead wastes the time of a lot of their honest customers.  Come on, Apple.  You can do better than this.