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Adolescents who face challenges also possess strengths and assets. Unfortunately, many are defined solely by their perceived deficits. In this study, we leveraged a nuanced dataset of adolescents’ challenges and socio-emotional strengths to explore how different challenges are experienced in clusters, and how cluster membership relates to socio-emotional outcomes. Our cluster analyses result in five overarching clusters: Predominantly Academic, Absenteeism, No Challenges, No Transportation, and Detention. Generally, adolescents facing reported challenges did not report significantly different coping skills or engagement in relation to adolescents facing none, although there were exceptions. This work can challenge notions that cast students as monolithically disadvantaged, and encourage educators to consider the complex, intersecting challenges and socio-emotional strengths of adolescents when supporting them.