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This case study investigates how a secondary teacher reflects on the modelling and teaching of historical contextualization in a Quebec classroom. Based on a qualitative case study of a 17-lesson sequence using historical films as interpretive artefacts, it analyzes the pedagogical strategies and professional knowledge mobilized. Findings reveal tensions between procedural routines and critical inquiry, and the difficulty of modelling interpretation without constraining student agency. Extending Huijgen et al.’s (2018) framework, the study highlights teacher reflexivity as a lever to navigate the gap between ‘knowledge to teach’ and ‘knowledge for teaching’. It shows how reflective practice mediates between epistemological commitments and classroom realities, redefining contextualization as a situated act of critical historical reasoning. Contributions target history education and teacher training.