Abstract
This study examines how teachers mediate upper secondary students' understanding of measurement through the strategic use of authentic real-life contexts, situated within the praxis of enacted classroom pedagogy. Measurement is a foundational mathematical domain, yet low-performing, disengaged students consistently struggle to develop transferable conceptual understanding. Attending to how teacher intention translated into enacted praxis, ethnographic methods captured moment-by-moment pedagogies through which real-life contexts were actualised revealing the conditions under which authentic contextualisation produced genuine mathematical engagement.