Update your repositories and install TOR.
apt-get update && apt-get install -y tor
If you want to use TOR with OpenSSH, you have to install another program called connect-proxy.
apt-get install -y connect-proxy
Setup OpenSSH to use TOR for all connections
However, this is not recommended, but here is how it works.
Add the following block to the top of your ~/.ssh/config file.
Host * CheckHostIP no Compression yes Protocol 2 ProxyCommand connect -4 -S localhost:9050 $(tor-resolve %h localhost:9050) %p
The command line syntax won't change at all.
Set up OpenSSH to use TOR for a specific connection
I recommend using TOR only for a specific connection. All other connections won't be affected.
Add this block to your ~/.ssh/config. You have to replace mydomain with the host domain name or IP address and myaccount with your user name.
Host mydomain HostName mydomain.com User myaccount CheckHostIP no Compression yes Protocol 2 ProxyCommand connect -4 -S localhost:9050 $(tor-resolve %h localhost:9050) %p
Set up OpenSSH to use TOR for a bunch of connections
Instead of setting up TOR for every single connections, you can do this for a bunch of connections at once. Following example shows how it works.
Host anon_* CheckHostIP no Compression yes Protocol 2 ProxyCommand connect -4 -S localhost:9050 $(tor-resolve %h localhost:9050) %p Host anon_mydomain HostName mydomain.com User myaccount Host anon_mydomain2 HostName mydomain2.com User myaccount Port 980
This way you know exactly if you're using TOR or not.
Conclusion
It is very simple to anonymize your SSH sessions if you know what you're doing. I've written this tutorial for legal purposes only. Using this is your own risk.