I saw a very interesting talk last year from someone who, as part of a company's security team, had set up a system that continually attacked the hashes of every employee's Active Directory passwords. If one was cracked, the employee would receive an automated email with a note containing the last few characters of their password and a suggestion to change it. I recall they also spoke on some security aspects of the…
I used to work at a University in the UK. One of my responsibilities was the email system. We constantly suffered targeted phishing attacks where the sender pretended to be from the IT department and required the recipient to respond with their password, for various made up reasons. Our spam filters captured most of these on the way in, but some still got through. And people replied. People replied all the time. Stud…
Did you consider regularly sending phishing emails yourself, and automatically call out anyone who reply anything at all to them? I mean, you won't catch quite as many people, but eventually most will learn, one would think.