There is a gap in the literature and a lack of clarity for how leadership efficiency and fidelity can be affected by cataloging dropout prevention programs in the educational sector. While several evidence-based dropout prevention strategies are available, their effectiveness for increasing leadership efficiency and fidelity is unclear. Thus, this study was guided by three objectives: 1) To explore the role of organizational leadership strategies in dropout prevention. 2) To explore organizational leadership practices associated with tracking and mitigating student dropout rates. 3) To make recommendations for leaders and policymakers grounded in best practices for dropout prevention in a large urban school district. This dissertation utilized a qualitative action research design to explore organizational strategies for dropout prevention based on these research objectives. The National Dropout Prevention Center's 15 Effective Dropout Prevention Strategies framework provided pre-coded themes and subcategories of dropout prevention efforts found in the educational sector for this study. In addition, archival data from a school district of over 350,000 students were analyzed in triangulation with other data for trustworthiness. Findings concluded that this study has national implications on public health, criminal justice, dropout prevention, educational leadership, social mobility, and social equity. Findings also concluded that: 1) No widely accepted organizational tool exists that provides leaders with a way of monitoring all dropout prevention strategies. 2) Educational leaders require evidence-based resource tools to align and match students with dropout prevention efforts. 3) The educational sector in the study is conducting multiple strategies to mitigate dropout rates. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]