Contemporary secondary technology education often does not mirror engineering practice. Whilethere is much rhetoric on the need for promoting active, authentic, and real-world professionalexperiences in upper secondary school, most technology education teaching remains traditional,and teacher centered. This study investigates the affordances for authenticity of role-play-basedproject work in a Swedish upper secondary software engineering course. The project requiredstudents (aged 17–18) to assume the role of software engineer employees at a web-designbusiness with the task of creating a website for a gaming company, where the course instructorassumed the role of the web business owner. The six-week project included the formulation of adesign plan, back-end programming, developing and refining the design and layout, adjustingcontent for accessibility, and publication of the web site. Inductive analysis of observations fromthe unfolding role-play in five student groups (total 22 students), and interviews with fourstudents and the teacher exposed salient themes related to authenticity of the role-play-basedproject exposed within teacher-student interactions and student intragroup interactions. Teacherstudent interactions revealed that the teacher exhibited various roles in the project, initially actingas a customer but also the responsibilities of a boss and a teacher-mentor. In the latter instance,students perceived the project as more school-oriented than authentic, expressing a preference foran external customer, and at the same time, the teacher tried to align the task with the project’scurriculum requirements. Student intragroup interactions showed that despite highly varied roles,students felt that their assigned roles enhanced the authenticity of their experience, although theywere unaware of what a real scenario might entail. Successful students emphasized theimportance of structured work and clear responsibilities to meet the project goal. The findingsshow that while role-playing is not necessarily always equivalent to reality, it was viewed as afulfilling and situated learning experience that simulated a real-world scenario, but which reliedon mutual confidence and responsibility between the role-players. Future work will combine thefindings with existing frameworks of authenticity to inform the development of role-playscenarios in upper secondary engineering education.