Symbolic interaction and stage-environment fit theories were used to examine associations between several aspects of the perceived school environment and youths' school-related experiences during the first semester of middle school in a sample of 390 youth living in a southeastern U.S. county. Perceived school environment included learning climate, academic rigor, teacher support, and school safety. School-related experiences included school satisfaction, engagement in school, and successful efforts to avoid getting into trouble at school. School satisfaction was predicted by a positive learning climate, teacher support, and school safety. Engagement was predicted by a positive learning climate and teacher support. Trouble avoidance was predicted by school safety. Some of these associations differed by prior grades, for boys and girls, and for Black, Hispanic, and non-Hispanic White youth. The findings provide important information that can guide development of support systems for youth as they enter middle school.