I’m forced to work on a Windows machine sometimes, which was a pain in the but in the past but got much better with Windows 11. None the less I use Wireguard to connect to my network which works super good for me with the official Windows client.
The downside was that my ssh_config had a config for one of my servers that looked like this:
Host osiris
HostName osiris.bouni.de
Port 2222
User bouni
When I connected to my Wireguard VPN I wasn’t able to connect any more with ssh osiris.
I knew that theres a way to have Match expressions within the ssh_config but only found examples for linux like this
Stack Overflow post
Match host web exec "hostname -I | grep -qF 10.10.11."
ForwardAgent yes
ProxyCommand ssh -p 110 -q relay.example.com nc %h %p
Host web
HostName web.example.com
Port 1111
Obviously "hostname -I | grep -qF 10.10.11." wouldn’t work on Windows so I was on the look for something that works on Windows and finally found this solution:
Match host osiris exec "wmic nic where 'NetConnectionStatus=2' get NetConnectionID | grep Goethestrasse"
HostName 192.168.178.100
Port 22
Host osiris
HostName osiris.bouni.de
Port 2222
User bouni
The name of my Wireguard config is Goethestrasse. As soon as I connect, there’s a network interface with that name and that’s exactly what the "wmic nic where 'NetConnectionStatus=2' get NetConnectionID | grep Goethestrasse checks for.
If the command returns success, HostName and Port of the config below are replaced and ssh horus will use the IP and port instead of subdomain and other port.