This all results in a significant gap in security caused by people’s unpreparedness to counteract social engineering. While many companies provide training for their employees, the majority of the population using information technology daily remains uneducated about social engineering threats. There is thus a need for a novel approach to education against social engineering attacks for casual users without high computing competencies that would take advantage of human psychology, just like the attacks themselves do. To address the dual problems of lack of cybersecurity literacy and increasing social engineering attacks, we propose integrating AI techniques to create a customized social engineering education experience that utilizes the principles of entertainment education. This effort will target non-security professionals. This project will: 1) use pretext design maps to train AI systems to generate social engineering scenarios; 2) use AI advances and humor theory knowledge to generate explainable humorous training schemas based on these social engineering scenarios; 3) apply the scenarios in a classroom setting and use learning patterns and specific psychological markers to refine AI-generated scenarios. The combination of these will result in an effective cybersecurity pedagogical tool for casual computer users powered by AI.