Host *.internal.local ProxyCommand bash -c 'timeout 3 nc -z %h %p || ssh -W %h:%p jump.internal.example.com' Host * ProxyCommand bash -c 'timeout 3 nc -z %h %p || ssh -W %h:%p jump.external.example.com' Host 192.168.0.* ProxyCommand bash -c 'timeout 3 nc -z %h %p || ssh -W %h:%p jump1.example.com' Host 172.16.*.* ProxyCommand bash -c 'timeout 3 nc -z %h %p || ssh -W %h:%p jump2.example.com' Host * ProxyCommand bash -c 'timeout 3 nc -z %h %p || ssh -W %h:%p fallback.jump.example.com'