This is my connection graph: user --> example.server on port 22 with username1/password1 --> example.server with username2/password2 on different port (some ssh subsystem port, e.g. 1000). I cannot connect any other way.

What would I need to do so I can write this and connect automatically to port 1000:

shh username1@example.server -s subsystem



The configuration option you are looking for is ProxyCommand. It was solved many times here or on ServerFault [1], so once more:

Set up your workstation with this ssh_config:

Host server2
  HostName ruapehu.example.com
  Port {server2 port}
  User {server2 user}
Host server1
  ProxyCommand ssh server2 -W %h:%p
  Port {server1 port}
  User {server1 user}

and whenever you will want to connect to server2, just do

$ ssh server2

You will need to set up passwordless authentication or enter both your passwords. Passwordless authentication is most secure when you will use ssh-agent and AgentForwarding option.

[1] Forward SSH traffic through a middle machine

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