Urban high schools that predominantly serve at-risk students have not been faring well; disproportionate numbers of minority children and poor White children have been dropping out. The purpose of this mixed methods study was to examine the effectiveness of leadership practices and dropout prevention initiatives in reducing dropout rates in 2 urban schools. This research was guided by empirical literature on various leadership practices that have proven successful. For the qualitative portion of the study, a case study design was used, in which 5 administrative leaders participated in in-depth interviews that captured the essence of their thoughts on management, the ways they portray leadership, and their contributions to organizational effectiveness. Likert-style surveys completed by a purposeful sample of 195 students and 7 administrative leaders provided the quantitative data. Coding and category construction were used in the analysis of the interview responses, and descriptive statistics were used with the survey responses.