Identifying factors that help or hinder the implementation of school environment interventions such as the Olweus Bullying Prevention Program (OBPP) is needed to inform strategies that bolster implementation quality in low-income urban middle school settings. We used qualitative methods to identify supports and barriers for OBPP implementation from the perspective of administrators, Bullying Prevention Coordinating Committee members, and teaching staff at two urban middle schools in low-income attendance zones that primarily served African-American adolescents. Interviews and focus groups with 42 participants (Mage = 46; 74% female; 79% African-American) yielded seven themes that impeded OBPP implementation: (1) lack of time, (2) unanticipated changes and events, (3) varying staff commitment and implementation consistency, (4) school context, climate, and structural changes, (5) difficulty identifying bullying incidents, (6) social media influences that exacerbated bullying behaviors, and (7) limited fiscal and staff resources. Participants also identified four themes that supported implementation: (1) endorsing the OBPP as seen by administrator prioritization of the program and staff presence, involvement, and commitment, (2) staffs' clear communication about OBPP roles and responsibilities, and teamwork and collaboration within and across levels of organizational leadership, (3) intervention dynamics (e.g., flexibility in class meeting delivery), and (4) logistics such as having support materials for class meetings and staffing resources. These findings inform OBPP efforts, especially those focused on enhancing program implementation in urban middle school settings located in low-income areas.