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Teachers’ working conditions are a key driver of teacher retention. This mixed methods study utilizes latent profile analysis (LPA) to explore variation in teacher retention based on a holistic measure of teacher working conditions, as well as focus groups with teachers to examine how working conditions are associated with teacher retention and how these associations vary by local context. Our LPA identified four classes of schools: supportive, structured, unstructured, and unsupportive. We find teacher departure was significantly less likely in unstructured and supportive schools as compared to unsupportive schools. Teacher focus groups identified emergent working conditions that contribute to teachers’ perceptions of their working conditions and are associated with retention decisions.