Difficulty rating: 8. Highly specific use case, highly specific setup, assumes that you know what these tools are already.
Let's assume that you have a couple of servers that you can SSH into over Tor as hidden services.
Let's assume that your management workstation has SSH, the Tor Browser Bundle and Ansible installed. Ansible does all over its work over an SSH connection, so there's no agent to install on any of your servers.
Let's assume that you only use SSH public key authentication to log into those servers. Password authentication is disabled with the directive PasswordAuthentication no in the /etc/ssh/sshd_config file.
Let's assume that you have sudo installed on all of those servers, and at least one account can use sudo without needing to supply a password. Kind of dodgy, kind of risky, mitigated by only being able to log in with the matching public key. That seems to be the devopsy way to do stuff these days.
Problem: How to use Ansible to log into and run commands on those servers over the Tor network?