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I want to set up a SSH connection through a https proxy, using the full HTTPS / SSL stack (to disguise the SSH traffic).

This should be possible using the CONNECT command on HTTPS server.

What programs can I use best to set up this proxy? I'm using Windows 7, and ProxyTunnel does not seem to work.

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Did you try corkscrew? It does exactly what you want.

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corkscrew or the -X CONNECT option of OpenBSD's netcat can do this.

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There is a bug in apache since a long time that causes CONNECT (mod_proxy) to fail when SSL is being enabled. That's why your proxytunnel does not seem to work. They appear to have fixed it since apache version 2.4.1 though.

Further information about the apache bug is found here: https://issues.apache.org/bugzilla/show_bug.cgi?id=29744

the link also shows patches for pre 2.4.1 versions of apache that fix the issue.

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