This study investigates the framing, implementation, and experience of role-play and challenge-based learning in design projects, and what aspects of authenticity they reveal in two Swedish upper secondary school engineering courses. In two different schools, students were to assume the role of engineering professionals and organise work with different roles and areas of responsibility, and act in suitable ways when interacting with ‘customers’ and ‘managers’. Observations and interviews with students and teachers revealed themes related to weak and strong role assignment and authenticity concerning learners, activity preparation, cross-cutting, and discipline-specific obstacles. Findings indicate that while role-playing is not necessarily equivalent to authentic engineering scenarios, it fulfils a substantial and situated learning process that may simulate real-world experiences, making it a compelling component of future engineering education. The study contributes novel knowledge on authenticity and challenge-based learning in engineering education, in particular, how teachers and students perform and perceive such projects.