[iamwpj]

I use this method for nested VPN connections. At work I have one VPN for main stuff and then once on that I connect to another one for more secure access. The workflow is Windows centered so typical users will RDP to the secure edge and then go from there, but on a Mac and attempting to SSH to machines was kludgy running from a separate desktop. I run openvpn to connect and use tinyproxy to catch web traffic (I have a separate browser with the proxy address set in it). Love the solution, it even passes MFA.