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Currently I am using an OpenSSH session (with the -D flag to enable dynamic application level port forwarding) as a SOCKS proxy while I'm accessing the internet through an unencrypted wireless access point. I have configured my Mac to use the proxy, however the network prefpane doesn't permit me to specify that it should use SOCKS5, which would force all UDP traffic over the proxy (it currently bypasses the proxy entirely). How can I make OS X use the SOCKS5 protocol, or what other solution would force all UDP traffic through the proxy?

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3 Answers 3

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You can't do that with SSH. OpenSSH client & server do not support UDP via Socks5.

You should use either OpenVPN or SSH tunnel device forwarding (option -w) to solve your task.

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If the need for UDP over the tunnel is for tunneled DNS resolution. The only solution I know of is to use Firefox with the following set network.proxy.socks_remote_dns = true, I believe this forces Firefox to use TCP only DNS requests that it forwards through the tunnel.

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I do not use ssh to anonymize/protect my connection but Tor. I launch Tor with Vidalia and then I configure my network connection in
System Preferences > Network > Advanced... > Proxies
I enable usually http and https, by setting the proxy to 127.0.0.1 port: 8118
For other traffic use 127.0.0.1 port 9050
This works fine for me. You can check if you are using Tor for https by redirecting your browser to https://check.torproject.org/

There is also the Torbutton in FireFox that do the same.

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I'm afraid this answer doesn't resolve my question. [The] TOR network is extraordinarily slow at best, which is why I tunnel through another machine of mine. I'm only concerned with encrypting the data while it travels unencrypted over the air. Anonymity isn't important to me. I would like to direct all UDP traffic through the proxy, as all my DNS queries still bypass the proxy and go over the air unencrypted. –  Ryan Tenney Sep 22 '10 at 3:22

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