how to use tails for ssh connection to windows vps?

Question

My friend has Windows VPS and he used Windows Remote Desktop tool and it was OK, but when he tried Tails, it was not working.

Maybe you have some other advice than me, he didn't succeed with my advice:

To make an SSH conection over Tor you'll need a small program called connect.c. It is available in many Linux distros in the pakage named connect-proxy or connect. You can try next command in tails terminal:

apt-get install connect-proxy

After all of that, to run SSH over Tor, run the following command. Substitute your username for mammamia and the IP address you wish to connect for 200.20.200.20.

ssh -l mammamia@200.20.200.20 -o ProxyCommand="/usr/bin/connect -4 -S localhost:9050 %h %p"

Answer 1

RDP in version 8 and higher uses UDP for communication. So if the server solely relies on UDP, you can't use it (see Can I use Tor through UDP Protocol?). Windows allows you to use TCP and UDP connections. Please check that the server allows TCP connections. This TechNet article describes where to find the settings.

Now you can connect to the server. Use either command line:

ssh -o ProxyCommand="socat STDIO SOCKS4A:127.0.0.1:%h:%p,socksport=9050" user@host

or change the ~/.ssh/config

Host foo
  HostName YOUR_HOST_NAME #(or IP address)
  ProxyCommand socat STDIO SOCKS4A:127.0.0.1:%h:%p,socksport=9050

Enter the correct host name or an IP address. Now you can connect to the host using ssh foo.

Answer 2

If you want to torify ssh connexion ... use torify or torsocks command (man torify / man torsocks) Or put that in /etc/ssh/ssh_config

ProxyCommand socat - SOCKS4A:localhost:%h:%p,socksport=9050

Answer 3

RDP always was a pain in the shell, so if you have explicit requirement of using it - elaborate OpenVPN server. You're connecting to it via TCP, pretty OK with Tor, and then inside VPN network you're talking to the Windows machine directly on both TCP, UDP and whatever you wish. If you need to use SSH for Windows - there's a WinSSHD that does the job pretty well and is using TCP only. If you need just a GUI tunnel for your windows server - a VNC protocol is good for that, TightVNC is free and open source.