This research article from the Journal of Educational Administration reports the findings of a study that identified positive outlier schools in Alabama, a state characterized by severe and widespread poverty, and studied the leadership approaches of their principals. The findings showed that five principals navigated successful schools in resource-challenged communities. 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; and (3) outlier principals understand their community’s challenges and focus on supporting students through a context-sensitive, relational approach that emphasizes assets over limitations.