The content filtering was really the locus of the issue I was trying to solve, as fanatical pointed out. To be honest, the Girlfriend wanted to play Neopets and it was filtered on the network. I’ve also been a user of that same network for years and I know the security of it as well as the people running it. True, they are incompetent.
To address all the concerns and comments I’ve received, I’ll start working on an article making use of a better solution, say STunnel. However, this particular article was aimed at a setup which a non-technical user could work through. No compilation, nothing. As far as I know, STunnel binaries are not available for OS X.
To those that complained of being specific to OS X or hinting at my lack of knowledge about this functionality in *nix: I come from a Linux background, not an OS X one. I know that it’s there. This was aimed at providing a guide for people using OS X. The way you write an interesting article is to pick a twist on a topic. Otherwise, it’s all been done before.
Also, I understand that this is not strictly anonymizing except for the content of your transactions. If you want heavy duty anonymity, you’re going to have to work with Tor/Vidalia, Freenet, or the now deceased IIP.
Thanks for all the comments and gripes. Keep your eyes peeled for Part 2 addressing these issues.
