Bullying prevention programs in the United States are being implemented in schools from kindergarten through high school to reduce rates of bullying behaviors. The bully prevention in positive behavior support (PBIS) model is an evidence-based, whole school intervention program. The PBIS model trains teachers, school staff, and administrators to model and provide positive reinforcement for children to decrease bullying amongst peers. This article addresses gaps in the current bullying prevention research by exploring challenges and potential modifications to the PBIS model based on staff perspectives of specific student needs. Utilizing focus group methodology, administrators, teachers, and support staff in a northeastern urban elementary school identified challenges experienced by students who were English language learners, impulsive, shy or sensitive, and female. The findings highlight the critical nature of school-parent relationships in addressing student, family, and cultural factors that influence the successful implementation of bullying prevention programs.