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. Students and staff. Even after being constantly informed about the problem and told to not reply to such emails. When they replied, the attacker would log in and start sending out spam.

Anyway, the format of our passwords was quite strict. I don't remember the exact rules, but it required "special" characters and lower/upper case letters and numbers and a minimum length etc. So what I did was write a system to scan all outgoing email. It would search that email for all strings which matched our password pattern. It would then attempt to authenticate against the Active Directory with each of those strings. If any succeeded, it would block the email, and the person sending the email would get a response telling them to not send their password via email. I would also be Cc'd in, so I could keep an eye on it.

This stopped several people a week from emailing out their login details to a phisher. I wrote about it here: https://www.grepular.com/Mitigating_Spear_Phishing - With links to the source code. I also later came up with a simpler solution and wrote about it here: https://www.grepular.com/Defending_Against_Spear_Phishing_wi...