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This chapter examines practical strategies to address issues related to poverty in small to mid-sized urban districts. Data clearly demonstrates that students in poverty perform at a lesser rate than their affluent peers. The greatest challenge facing public school leaders is educating students in poverty. This chapter is informed and supported by the existing educational research base and drawn primarily from our authentic experiences as educational leaders in public schools. The information shared is realistic, practical, and uniquely derived from day to day public school life.