I am using a VPN software which, like all VPNs, changes the system configuration in certain ways to make use of their servers.
Sometimes, I need to use an SSH tunnel proxy. I use Sidestep which automatically sets and unsets the proxy settings on the system when I need to use it. And I'm trying to make sure that when I'm using the SSH tunnel proxy, all the connections are still going through via VPN first, then to the SSH tunnel.
My fear is that when I turn the proxy on, the settings are overridden and my machine directly connects to the proxy server only.
So I connect first to the VPN, then to the proxy server. When I visit a site to check my IP, I see the last IP of the chain (the ssh tunnel proxy).
How can I make sure that the local machine is not directly connecting via the SSH tunnel, overriding the VPN settings?
I tried with say, the
traceroute google.com command, but it returns an unknown host error when using both the VPN and the SSH tunnel (same with other commands such as ping). When using JUST the VPN or the proxy, it works as expected, showing two different routes.