Purpose: Schools in resource challenged communities require principal approaches that break patterns of low expectations and low student achievement. This study identifies Alabama's "outlier" schools that have been consistently successful in attaining higher student outcomes than their neighboring schools despite their similar community conditions. Then, it describes the perspectives and practices of principals leading these outlier schools. The purpose of this paper is to discuss findings on principal leadership in five of Alabama's outlier schools. Design/methodology/approach: In a sequential, explanatory mixed-methods design, the authors first use state administrative data to identify which Alabama schools had better results than their peers as evidenced by standardized testing between 2016 and 2020. Then, through semi-structured interviews, they examine the beliefs and approaches of five principals who are currently leading an outlier school. The frame of contextual leadership provides a deeper understanding of how these principals navigate successful schools in the midst of challenging community influences. Findings: The evidence demonstrated that (1) community factors of low education, high unemployment, single-parent households and generational poverty are associated with considerably lower levels of student growth and achievement; (2) measured school and community factors do not explain student growth and achievement in these outlier schools; (3) outlier principals have a realistic view of their community's challenges but focus on supporting students through a context sensitive, relational approach that emphasizes assets over limitations. Originality/value: While research has attended to leadership in turnaround schools and effective schools, there is little literature on principals leading in positive outlier schools. This study contributes to the literature on school leadership in resource challenged contexts by identifying high performing, resource challenged schools and then showing the perspectives and practices of principals who lead in schools that have consistently achieved better than expected student outcomes. It extends the construct of "outlier leadership" in education and connects it to contextual leadership in schools.