In the pursuit of understanding declining levels of participation from scholastic Health and Physical Education (HPE), ethnographic research has been increasingly utilised as a tool to explore the intersubjective and intrasubjective meaning-making processes that concurrently invite or dissuade participation. Despite the ostensible epistemological benefits of deploying ethnographic research as a vehicle for better understanding contextual HPE (dis)engagement processes and meanings, a critical methodological discussion of the actual implementation and positionality of these methods is largely absent in the extant literature. Reflecting on an ethnographic study conducted with adolescent boys at a Canadian elementary school, this paper provides HPE ethnographers with a series of methodological deliberations, and reflexive points of departure for consideration in the design and implementation of ethnographic research. Specifically, this paper elucidates the process of rapport building with teachers/students, the omnipresent tensions, ethical dilemmas and triumphs that can emerge during ethnography, and the various socio-contextual interview factors that can influence data generation.