Teacher professional learning provides opportunities to enhance understandings and practices for those directly involved in children's learning. The expectations placed on providers of professional learning are frequently shaped by mandates beyond their control and or expertise. In this paper, we examine how the complex set of philosophies framing Sport New Zealand's "Play.sport" initiative, a school-based programme to enhance experiences in Physical Education (PE), Physical Activity (PA), Physical Literacy (PL), play and sport for young people, were understood and enacted by professional learning providers. The implementation framework centred on a workforce of Facilitators, Mentors and Activators providing professional learning in participating schools. Empirical evidence was gathered from interviews, field/meeting notes and observations to illuminate how the workforce consistently grappled with layers of complexity required to understand and enact philosophical and policy mandates associated with PE, PA, PL, sport and play. Our findings demonstrate the need to reconsider the delivery of professional learning and development initiatives. We conclude by reflecting on how our work as an academic community, undertaken with an intention of enhancing practices in PE, may be unintentionally increasing complexity and confusion.