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While participation in structured activities has generally positive effects during adolescence, the context and the quality of participation often shape those effects as much as the specific activity type. Qualitative methods offer useful tools for better understanding those activity contexts and qualities. This analysis thus draws on comparative ethnographic case studies using mixed methods to contrast activity participation at 2 high schools serving differing socioeconomic status (SES) communities. Quantitative survey results from adolescents in both the schools and across sports, arts, and service/leadership activities show similar, and consistently positive, developmental experiences. Yet, qualitative analysis demonstrates evident differences in the social organization of activities at each school related to resources, opportunities, and cultural logics. Examples from basketball, theater, and community service programs suggest that this social organization differentially associated with more asset- or deficit-oriented discourses. These discourses in turn differentially associated with the meanings of developmental characteristics such as initiative, teamwork, and identity exploration. Adolescents in the higher SES context, for example, had opportunities to cultivate talents and interests through consistent support, while the discourse in the lower SES context led adolescents to focus on overcoming challenges and obstacles. Such contrasting experiences, though each potentially valuable for adolescent development, suggest the possibility that overall positive psychological experiences with extracurricular activities may sometimes obscure meaningful developmental differences. Such qualitatively observed differences deserve more attention, particularly for understanding relationships between activities, developmental characteristics, and inequality.