Role playing is a teaching method widely used to enhance students learning and engagement, by allowing them to adopt specific roles and interact with others in simulating real-world scenarios, thus applying their theoretical knowledge in a practical context. In Software Engineering Education (SEE), role playing may help students to develop key skills (like teamwork, problem-solving, and critical thinking), to understand the complexities and challenges of software development, and to appreciate the importance of collaboration and effective communication. To use role playing effectively, SEE teachers need to understand the challenges that arising from using it. This paper presents the design, execution and results of a rapid literature review to identify these challenges. Several well known digital libraries (Web of Science, Scopus, and IEEE Xplore) yield 44 articles, which after inclusion/exclusion filters left a total of 23 articles. Key findings are that: (1) most role playing is used to teach skills linked to software development and teamwork/“soft skills”, and secondarily to software design, quality assurance, and process management; rather than project management or quality assurance; (2) challenges and generic considerations for implementing role playing were identified; and (3) challenges for applying role playing in SEE were identified by virtue of the SE specialty classification. In summary, role playing is a mature teaching technique used to in other fields, and has made limited inroads in SEE, mainly in disciplines dear to agile development (like development and teamwork).