We connect Machine B to our Ligolo instance (through the listener on Machine A):
We create another tunnel interface (ligolo2), we route the internal IP range through this, we remove this internal IP range from our first tunnel interface:
We now swap to our new agent (note we pass our new tunnel interface):
This should look as follows in Ligolo:
When we access any 192.168.210.0/24 host we will access it through our pivot on Machine B.
Note that you can also triple (or more) pivot with this method
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On Machine B
.\agent.exe -connect 10.10.14.15:53 -ignore-cert
On Kali
sudo ip tuntap add user kali mode tun ligolo2
sudo ip link set ligolo2 up
sudo ip route del 192.168.210.0/24 dev ligolo
sudo ip route add 192.168.210.0/24 dev ligolo2