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Configuring SSH for Pivoting

You’re on a pentesting engagement and you’ve discovered a dual homed machine that allows you access to a subnet you can’t access directly from your attack machine. Assuming you’ve compromised at least one machine on the initial network, you can use it as a proxy to other machines on the “hidden” subnet.

The ssh client has an often-overlooked configuration file that resides in your ~/.ssh folder. You can configure things in here that are specific to certain hosts or you can set default configurations for every host. In order to access remote networks, wouldn’t it be nice to shorten a command like:

ssh -l user -L 127.0.0.1:5432:132.31.321.123:5432 -p 20222 -i ~/.ssh/db/id_rsa remote.server.com

to something like:

ssh mount_psql

SSH Config file

This file has a lot of configuration options, but we’re just going to focus on the one’s that help us pivot through 2+ networks.

ControlMaster

Enables the sharing of multiple sessions over a single network connection. 
When set to ''yes'', ssh(1) will listen for connections on a control socket 
specified using the ControlPath argument. Additional sessions can connect 
to this socket using the same ControlPath

ControlPath

Specify the path to the control socket used for connection sharing as described 
in the ControlMaster section above or the string ''none'' to disable connection 
sharing

ProxyCommand

Specifies the command to use to connect to the server. The command string extends 
to the end of the line, and is executed with the user's shell. In the command 
string, '%h' will be substituted by the host name to connect and '%p' by the port.

Ok, so the first two aren’t strictly necessary for the pivoting, but subsequent connections to the same host will just reuse the same authenticated socket, so it’s lighting fast.

If you have the passwords for all the machines in your pivot chain, the client should ask you for each of them, but the whole process is much smoother if you upload keys to each of them. The cool thing about the ssh config file is that any program that uses ssh on the backend, can also use this file. So if you configure a server entry called skynet

ssh skynet
scp file.txt skynet:/tmp
rsync -avr skynet ...
ssh-copy-id -i ~/.ssh/id_rsa skynet

^ All of those work.

So let’s configure our ~/.ssh/config file. Let’s also assume root login is enabled on all the machines and that we’ve already copied our ssh keys onto the remote machines.

ControlMaster auto
ControlPath /tmp/ssh_mux_%h_%p_%r
ServerAliveInterval 60 

Host first_hop
  Hostname 123.123.321.123
  User root
  IdentityFile ~/.ssh/id_rsa

Host second_hop
  Hostname 321.321.345.345
  User root
  IdentityFile ~/.ssh/id_rsa
  ProxyCommand ssh -w %h:%p first_hop

Host skynet
  Hostname 666.666.666.666
  User root
  IdentityFile ~/.ssh/id_rsa
  ProxyCommand ssh -w %h:%p second_hop

With this configuration, we’re able to connect to skynet, which is 2 subnets removed from our current one, with the command ssh skynet. Likewise, if we want to create a dynamic tunnel to allow for proxychains usage, ssh -fNTD 9050 skynet should do the trick. Then proxychains nmap... to your hearts content!

The ProxyCommand directive in skynet is, in a way, declaring a prerequisite ssh connection to second_hop. The -w flag states that the client should just go ahead and forward and STDIN/OUT through the next connection.

That’s it. Go forth and PIVAAAT!

Additional Resources:

SSH Client Configurations Docs