Background: Establishing and maintaining a positive, inclusive social climate in school is essential, especially given the many potential social pressures that make school a toxic environment for vulnerable students. We explored middle school physical education (PE) teachers' perceptions of the factors that influence the implementation of social-oriented approaches to include overweight and obese students. Methods: We used a qualitative multicase study design guided by the Social Ecological Constraints model to study 9 PE teachers' perspectives and actions. We analyzed the transcripts of semistructured interviews, field notes, and artifacts related to teaching, PE programs, and school policies. Trust was established in conventional ways. Results: Social-ecological factors influenced teachers including program and school culture, policies, and norms of collaboration. Teachers acted beyond their instructional setting level strategies and used school-program level strategies to socially include overweight and obese in PE. Conclusions: Some environments challenge employment of more than simple accommodations and a caring attitude; in others, teachers can collaborate with other school personnel to teach social goals through negotiating constraints, creating ingenious modifications and interactive tasks, and incorporating personal and social skills as a primary curricular goal.