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We have tried using latest sshuttle on Mac OS X Mountain Lion, but there is a bug which messes with kernel variables and by this breaks internet connection. On the machine where we tried it we had to reinstall system since issue did not seem to be fixable. However we perfectly use it on Linux.

So I wonder if there is any analog of sshuttle for Mac that will allow us pipe all connections through SSH tunnel?

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I found this SU answered question to be relevant; I was unaware that mDNSresponder was how the OS determined the state of the wireless connection..

Also, I haven't used it personally, you might wish to evaluate MacProxy:

Features:

redirect your Mac's network traffic to any compatible SOCKS or HTTP proxy server

works with browsers (Safari, Firefox), email (Mail), chat (iChat, Skype), FTP, telnet, and many more network applications

enable and switch the active proxy conveniently from a menulet

track session statistics including the number of active connections and data sent/received

DNS resolution through the proxy server

secure browsing by hiding your IP address

support for SOCKS proxy protocols including versions 4, 4a, and 5

support for HTTP/web proxy protocols including transparent, non-transparent, and connect

SSH tunnel support - connect securely to a remote Mac to prevent snooping over WiFi networks

rules - proxy or ignore connections based on IP addresses, ports, domains (with wildcard support), and applications

quickly determine which proxy protocol a server supports using the built-in proxy checker

anonymize requests option (HTTP non-transparent only)

multiple user support - works for all users on a Mac

32/64-bit universal preference pane, application, and kernel extension

logging support

What's new in MacProxy 2.0.4 (history): Mac OS X Mountain Lion (10.8) compatibility

  • This doesn't work for all connections. Only for certain applications that have proxy option builtin. In my question I mentioned that I need to pipe all the connections through ssh tunnel the same way as sshuttle does. – Alexey Kamenskiy Jan 2 '13 at 9:37

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