Playful learning has become a common practice in Denmark, across primary and secondary education, however, the phrase playful learning might sound like a paradox, because learning and play suggest opposite values. In playful learning, play is approached as a learning resource, able to foster understanding and critical thinking. In the Occupational Therapy (OT) education, there has been a rich exploration of different forms of digitally mediated role-play, to enable students to prepare beforehand to engage with patients, enacting clinical scenarios with each other. Current studies in OT education focus on the learning impact of digital media and role-play, not investigating how students experience their play, which is an essential pre-condition to learning. Starting from these premises, I conducted a design-oriented research study, involving students and teachers in OT in Denmark, to investigate how students experience their play during mediated role-play activities. Results show that playful learning is a complex sociomaterial practice, framed by power relationships embodied by the provided digital media, the relationships among the participants, and the institutional context. Within this framing, play is continually negotiated among the teachers and the students, who manage to gain room for self-expression through observable changes in play moods and practices.