I had the problem to connect to a SSH Host through a HTTP Proxy. I could run it with Putty, just entering the host and port in the proxy configuration section. Fine so far, but I want to clone GIT repositories from this host, git clone ssh://firstname.lastname@example.org. So Putty was out (maybe I could tunnel…). So I used this solution: Install basic Cygwin Install packages openssh, git and corkscrew Setup ~/.ssh/config (where 10.10.10.10 is the HTTP proxy host and 8080 the http proxy port. Host host.org ProxyCommand corkscrew 10.10.10.10 8080 %h %p That was all, I setup my SSH key and could connect.