For over twenty years, the Colloquium for Information Systems Security Education (CISSE) has been the sole 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.