District administrators face concerns over students dropping out of school without a high school diploma. District personnel in a Mississippi urban school district identified specific curricular, instructional, and co-curricular factors that prompted students to leave school. The purpose of this bounded qualitative case study was to explore perceptions of principals, teachers, and counselors regarding factors that influenced students' disengagement and dropping out of school. Battin-Pearson's theory of academic mediation, which attributes poor academic performance and student-centered learning to students dropping out, framed this study. The research questions focused on how district personnel identified and monitored at-risk students and provided interventions to prevent them from disengaging and dropping out. A purposeful sample of 2 principals, 5 teachers, and 2 counselors, who had knowledge of dropout prevention strategies, volunteered and participated in semistructured interviews and classroom observations. Data were analyzed inductively using segment and thematic coding. Results indicated a multi-tiered system of support was used to identify and monitor at-risk students. Participants expressed a need to build cohesive and collaborative learning communities and relationships, provide student guidance and support, engage more with students, and provide targeted professional development (PD) for educators. Based on these findings, a 3-day PD was developed to address student engagement and dropout prevention. These endeavors may contribute to positive social change by providing educators with learner-centered strategies through a collaborative, flexible blended-learning PD aimed at identifying and assisting at-risk students, resulting in an increase in graduation rates and reduce in dropouts.