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I seriously doubt there is a good, legal answer to my question, but here goes. Work has blocked anything to do with iTunes, MP3s, streaming media, etc. I understand why since everyone was maxing out our bandwidth, but I've got an odd issue.

I've brought my MP3 library to work with me via harddrive, but I can't play a lot of my songs since they were purchased through iTunes and I can't get iTunes to authorize me since the URL is blocked...see what I mean?

I guess that I could burn all of my purchased songs on my home machine to CDs, then bring them to work and have iTunes import them, but that would take a lot of CDs (I'm assuming I would have to make an audio CD and not a Data CD with MP3s on it.)

Any suggestions for me?

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Have you tried updating to the DRM-less songs? I'm not sure if they still need to do the authorization check or not. The other thing you could try is configuring a proxy via SSH or something. A lot depends on what your work DOES allow outbound. iTunes works primarily over http and https, so I don't understand how it would break unless they were also blocking all web traffic as well. –  peelman Jun 30 '10 at 2:49
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2 Answers

I am the same person as the asker of the question, but can't login via OpenID from my work computer. Anyway, I didn't find a specific answer for my question, but I did finally get my job to open up the exact right url to let iTunes authorize my account.

From my machine, sniffing packets using Wireshark, I found this IP address and domain name that needs to be unblocked so that iTunes can connect to the store to verify my username and password.

63.97.94.11 ax.init.itunes.apple.com

Your mileage may vary depending on how cool the IT guys are about this kind of thing, if the url is always the same, if the IP address is always the same, if Apple changes how things authenticate in the future, etc.

Good luck!

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Next step: get OpenID opened up? ;-) (Or: set up your own OpenID service if you can host some code yourself, like in PHP.) –  Arjan Sep 25 '10 at 11:58
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Install Vidalia, it's an all-in-one package with the Tor onion router and associated proxy stuff. If you can get Tor to connect to the outside world, you'll be ok just by configuring localhost as a proxy. That's for OSX, if you're on windows there are similar packages with tor & proxy.

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