It can if that machine creates a tunnel outbound. Installing cygwin and openssh should suffice. Keepalives should be enabled and the client should be called i

It can if that machine creates a tunnel outbound. Installing cygwin and openssh should suffice. Keepalives should be enabled and the client should be called in a bash for-loop to reset the connection when it goes down. Use ssh to create a gateway port on the remote end. You would then RDP to that remote host which could be a cheap VM. The openssh-server on the remote end would need to be configured to permit gateway ports. The remote VM should only allow you to connect to the gateway port. Security can be improved by binding your gateway remote port to 127.0.0.1 on the remote end and then accessed via SSH port forwarding on your remote client that would be accessing the Windows 7 machine. Here is an example a school gave to its folks [1]. One would replace the target servers with their own personal VM. There are additional examples on SuperUser [2] and youtube that may be helpful. Search for "RDP tunnel over SSH gateway ports" [1] - https://help.ece.gatech.edu/windows/remote-desk https://help.ece.gatech.edu/windows/remote-desk [2] - https://superuser.com/ https://superuser.com/