For over twenty years, the Colloquium for Information Systems Security Education (CISSE) has been a forum in which the members of the academic field of cybersecurity have gathered to present and discuss new ideas. CISSE was first established to provide a single place to conduct productive conversations between a variety of government, industry, and academic on the topic of cybersecurity education. Ideas arising from those discussions have led to new and improved content and curricula for cybersecurity teaching.