This qualitative interview study investigates the perceived barriers and enablers to implementing and sustaining individualized positive behavior supports (IPBS) by school-based team members across five stakeholder groups. The findings reveal specific factors across five broad themes: (a) school culture, (b) administrative leadership and support, (c) structure and use of time, (d) ongoing professional development, and (e) family and student involvement. The findings offer insight into the interconnectedness of factors that can interfere with or support IPBS in schools and suggest implications for practice and future research. (Contains 2 tables.)