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Teacher retention studies often focus on why teachers leave the profession, but this study foregrounds rural community assets and the strengths of rural schools to understand why teachers stay. Using a collective case study design and asset-based ecological framework, rural educator perspectives form the building blocks of three rural Wisconsin school district cases. In-depth descriptions of each school community provide empirical evidence of the local characteristics that contribute to teacher satisfaction and retention. Comparison across the three cases reveals that school and community characteristics, and the interaction between the two, influence teachers’ decisions to remain. Our findings suggest that the contours of the school-community relationship influence rural teacher retention by shaping the classroom environment and by filtering macrosystem pressures locally.