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This study investigates the intersections between caring school leadership, school context, and organizational learning. Using case study data from two schools, we examine how two principals who prioritized caring in their school mission and relational approach were influenced by the context of the school, and how caring and context textured efforts to foster organizational learning. We found that school context and the accompanying leader beliefs shaped the structures and practices where organizational learning occurred, and thereby influence the diffusion of organizational learning in the school and the flexibility by which organizational lessons can be applied.