The purpose of this study was to explore interpretations and implications of head coaches’ use of humour in three national Paralympic teams from the perspective of athletes and integrated support staff. We conducted six focus groups with 19 Paralympic athletes and individual interviews with 10 support staff members across the teams. Our reflexive thematic analysis resulted in two overarching themes that helped us understand how humour influenced feelings of psychological safety in the team environment, as well as considerations or challenges with using humour as a coaching strategy, including miscommunication or misunderstanding. Relational awareness, emotional intelligence, and effective communication were identified as important coaching competencies to consider when implementing humour as a leadership behaviour, particularly in an environment where power differentials of status and disability were present. The study was among the first to explore interpretations and implications of humour as a coaching strategy from athletes and staff in the high-performance parasport context. Coaches who implement humour within their environments are encouraged to reflect on the receivers of the interaction and how to maximise the facilitative rather than debilitative functions of humour as a “double-edged sword” to ultimately promote team satisfaction, well-being, and success.