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This qualitative, multiple-case study addresses an existing gap related to school-level leadership and potential influences on the implementation of differentiated instruction. Employing elements of both the Situated Learning Theory and Sensemaking Theory, this study explores the implementation of differentiation from the perspective of teacher learning within the context of three high performing middle schools, in three school districts. Four identified expert differentiating teachers were included to gain a deeper understanding of the influences within each school, on teacher learning and ultimately on implementation. Employing the mediating construct of school-level leadership, data was collected and analyzed over a nine month period. The findings capture the reality of the classroom teacher and uncover influences on teacher learning and the implementation of differentiation.