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Chasing The American Dream

August 11, 2005


I could have titled this post “48 Hours” just as easily because that’s how long it took me to restore my iPod songs to iTunes on my new laptop. This is one serious drawback to an otherwise near-perfect invention. I know we all love our iPods, but god forbid we change computers. Yes I’m technically challenged, no doubt about it, but Apple has made the transfer process much harder than it needs to be. Oh sure, I may have made what could have been a simple process into a convoluted mess, but the process itself, in my opinion and in my best Spock imitation, is highly illogical. The main difficulty is that Apple has decided that we can only transfer songs one-way, meaning we can only transfer songs from the computer to iTunes. Amazingly, we can’t transfer songs from our iPod directly to iTunes. Can you imagine how simple that would be? Yeah, take the iPod, plug in your USB cable and click transfer. Voila! But this is not the case, and so I hope my pain and suffering and lessons I learned will help those of you who may need to do this in the future. OK class, grab a pen and paper and let me see if I can recap the process for you.

The first thing I did was go to the Apple iPod website for help. I typed in my question, “transfer songs to a new computer,” and it spit me out a link to specific directions on how to accomplish this. By the time I read step one, I was already behind the eight-ball. So listen up, this is very important. You’ve got to copy your iTunes music library from your old computer to your iPod. You basically have to you’re your iPod into a storage device, copy the library file onto the iPod, and deauthorize the old computer. The instructions tell you how to do this. Unfortunately for me, I only did the deauthorize part and turned in my work laptop before doing the file transfer. Had I done this, then in theory, I could have copied the iTunes library file from the iPod to the new computer under the iTunes directory. In theory, but I wonder if it would truly work that easily because I eventually got there, but still had problems.

Once I realized that I hadn’t copied the old file, I located Apple’s customer service number and called for help. But I got no help. Apparently, I owned a Generation 4 iPod from HP which meant that Apple couldn’t help me. HP had to help me. So the guy gave me the HP customer service number to call. So I called and relayed my problem to the tech dude. But the dude said he couldn’t help me transfer my songs directly from my iPod to iTunes because Apple forbids it due to some copyright or privacy bullshit. He said he knew how to do it, but he couldn’t tell me. So he just told me to Google it and that I would find out how to do it.

So I Googled, and sure enough there were plenty of sites advertising that their free software could download songs from iPod to iTunes. So I did some clicking and researching. The main problem I was having is that most of the software was for Macs and not for Windows. It was difficult to find a program to work for Windows. Once I did, I read some reviews from users and they were, at best, a mixed bag. I’d now been working on this for five hours and was getting impatient. I was beginning to wonder if I’d ever see my 500 songs again. I finally decided to call CompUSA where I bought the iPod and ask them for help. The guy there told me he had some Windows software called Tune Transfer that could accomplish the transfer. It was only $19.99 so I decided it would be well worth it so off I went.

I got back home and was full of confidence, promise, and hope. I quickly lost confidence when I opened the software box. Inside the standard square-shaped software box, I found only a cheesy plastic tray containing a black CD jewel case with an even cheesier black and white label. It looked like some 13-year-old kid had put this together. I joke, but it’s probably true, ya know? But like they say, you can’t judge a book by its cover.

The instructions said the software would enable me to copy my songs off my iPod to any new computer. I mean, that’s why I bought it, right? But the execution wasn’t exactly what I had in mind. I still thought I’d be able to easily go from the iPod to the new computer. Wrong. It’s never simple is it? My first conflict came right off the bat. It said I needed to connect my iPod, but if I did, I risked losing all my songs because iTunes kept trying to update my iPod to an empty library. Empty library = empty iPod. Good grief. So the software didn’t recognize that my iPod was connected and it listed no songs to transfer. I kept unplugging and replugging and I don’t know what I did, but it finally recognized the iPod and with a sigh of relief, I saw all my songs listed and ready to transfer. That was the good news. The bad news is that it didn’t recognize my playlists so I had to recreate all of them. I finally took a break after being at this for 12 hours.

The next day, I continued creating my playlists and then clicked the ‘transfer’ button and, lo and behold, the files were transferred into iTunes. Wow, I actually saw my songs. Wow, I actually played my songs! But one problem; the songs transferred, but the playlists didn’t. So I had to once again recreate all the playlists and copy/paste the songs into each playlist. Then I had to run through each of the 500 songs to ensure they were authorized to play and to restore the equalizer and volume settings that I previously had. Good grief. I finally finished up around 10 p.m.

This was an extremely frustrating process, but the bottom line is that I got my songs back. Whew! So if any of you need to do this crap in the near future, feel free to ask me for help. Or maybe by then, Apple will come to its senses.


  • i will definitely be consulting this post if and when i ever choose to get a new computer!

    By Blogger Amanda, at 1:58 PM, August 11, 2005  

  • That sucks!

    By Blogger Lyss, at 6:12 PM, August 11, 2005  

  • You are my hero because I have GOT to get this software. The 100 or so songs on my ipod were all from my mom's computer and I will be getting one of my own soon. I will DEFINITELY be consulting this post when the day finally gets here.

    By Blogger Elle, at 11:50 AM, August 12, 2005  

  • Ok, so I have no idea what I'm talking about, but here is my bit of advice.

    What about investing in an external hard drive? My cousin has one and he says the only thing he puts on it are his songs. Says its fabulous. And he has a Mac and a PC. I have no idea if the external hard drive works with both the Mac and PC, but there ya go, thats my advice :)

    By Blogger catsteevens, at 2:34 PM, August 12, 2005  

  • feel glad that you don't have the 7000 songs on my itunes to convert! ;-)

    By Blogger ME, at 1:16 PM, August 16, 2005  

  • oh yeah, and mine are on an external hard drive.

    By Blogger ME, at 1:16 PM, August 16, 2005  

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