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Is there a way to make different Mac OS X applications use different SOCKS proxies? I've had no luck using tsocks with Mac OS X applications like Skype, Mail, or Chrome, always segfaults.

I believe that sshuttle could handle Mail by mapping specific IP ranges through the proxy. Or maybe I could exclude all but the target ranges in Mac OS X's proxy settings.

IP ranges aren't well suited to proxying Skype or Chrome connections however. I understand that a peer-to-peer application like Skype might require a more complete solution, but Chrome should survive tsocks style library replacement nicely.

I could perhaps run multiple FireFoxes simultaneously with different proxy configurations, well that already happens with Tor, but It'd be lovely to find a broader solution.

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You can try to "encapsulate" a new process to use a SOCKS proxy you want so the process will not know that you are using proxy - a tool to do it is tsocks. It'll also works with software that does not provide proxy configuration.

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