This qualitative case study was designed to explore how master teachers in transfer high schools learn the competencies they perceive are required to engage at-risk students so that they persist and graduate. The study is based on the following assumptions: (1) The requisite teacher competencies can be defined and identified and, in fact, strengthened. (2) Organizational context matters. School organizations that are most successful at the task of helping at-risk students graduate are the ones where the systems, structure, organizational culture, leadership, climate, and resources support the development of teaching competencies required to help students graduate. The sites for this study were nine transfer high schools located on the East Coast of the United States. The primary sources of data were: in-depth interviews involving thirteen teachers and ten principals and assistant principals in nine alternative high school settings, document analysis, and unobtrusive observation of classes. The study was framed by three theoretical frameworks: (1) self-efficacy beliefs as a motivating factor for teachers who choose to teach in alternative schools for at-risk youth (Bandura, 1989, 1993, 1997). This theoretical framework is rooted in social-cognitive theory of human behavior. (2) Adult learning theories, specifically, experiential learning. This study set out to examine how the study participants learned the competencies required to engage at-risk youth. One key finding was that participants learned both through the attainment of formal academic credentials and professional development as well as informally through dialogue with other teachers. Furthermore, several competencies were identified by participants as requirements for the successful engagement of students: (1) the ability to build relationships; (2) the ability to know what and how to teach; and (3) the ability to overcome school challenges. The principal recommendation resulting from the study is that teachers, principals, and assistant principals focus on building communities of practice. Communities engaged in inquiry and dialogue may enhance teacher self-efficacy beliefs and the development of the kinds of competencies that lead to student engagement and retention. [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/en-US/products/dissertations/individuals.shtml.]