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tun2socksdoesn't require SSH and a server; the example on their site is for using SSH to create the SOCKS proxy in the first place. If you already have a SOCKS proxy, it's entirely unnecessary. And yes,iptableswas a wrong way on my part. OS X, being based on BSD, usesipfwrather thaniptables, which is for the Linux kernel. As for it being complicated, you may be able to find a frontend that'll set it up for you in an easier to use manner, but I've no experience on this matter. It being complicated at a low level anyway has a lot to do with why it is so capable for the job.ipfweasier.