This study examined the role of hypermasculinity as a form of reactive coping among urban African American adolescent males (ages 12–17) and assessed the extent to which hypermasculinity is influenced by youth appraisals of how adults in their school and community perceive them. Two research questions were addressed: (a) Do adolescent males who report negative community and school experiences use hypermasculine attitudes as a coping response? (b) Do the effects of perceived negative school and community experiences persist, if they are present at all? Participants in the study were 241 African American adolescent males who attended public schools in a large southeastern city. Associating youth-reported questionnaires on perceived teacher expectations and perceptions of community challenges from one wave of data on hypermasculine attitudes within the same year and 2 years later, the results indicate that hypermasculinity attitudes stem from negative perceptions in the community and school contexts. Also, hyper-masculinity attitudes were associated with these negatively perceived experiences across time. When examined longitudinally, negative experiences in the community had a stronger relation to hypermasculinity than similar experiences at school.