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Teacher attrition is a major problem: it disrupts learning, is costly, and is especially prevalent among STEM teachers. Here we asked how school environment and individual factors (demographics: age and gender) interact to influence attrition. We also tested whether department policies, such as the presence of senior teachers as content coaches, can improve retention. We evaluated ten years of administrative data for public high schools in Connecticut. School environments correlated to teacher attrition, but the influence was not felt equally amongst teachers of different backgrounds. Neither did content coaches improve retention equally for teachers of all backgrounds. This work improves our understanding of the hierarchical nature of the problem of teacher retention and the limitations of proposed solutions.