Related question. I’m just now trying to figure out how to do a second jump:-)
I’m using the Proxy Jump to go from my mac to a VirtualBox VM that is connected to another network on VPN. The direct connect to the first host on that network is easy. The Proxy Jump is to my VM on 127.0.0.1. Then I go to the first host. How can I do a second jump in the same connection? The first host is the gateway I need to go through. It’s like jumping through two bastion hosts.
With ProxyCommand I can do that by referencing another entry in the ~.ssh/config file
ProxyCommand ssh -o TCPKeepAlive=yes -o ServerAliveInterval=50 -C -W destinationIP:22 BastionHostIP
BastionHostIP is the gateway on the VPN network.
Does it make sense?