Passwords are ubiquitous and are poised to stay that way due to their relative usability, security and deployability when compared with alternative authentication schemes. Unfortunately, humans struggle with some of the assumptions or requirements that are necessary for truly strong passwords. As administrators try to push users towards password complexity and diversity, users still end up using predictable mangling patterns on old passwords and reusing the same passwords across services; users even inadvertently converge on the same patterns to a surprising degree, making an attacker’s job easier. This work explores using machine learning techniques to pick out strong passwords from weak ones, from a dataset of 10 million passwords, based on how structurally similar they were to the rest of the set.