Scholarship regarding adolescent resilience has typically defined resilience as the absence of negative outcomes rather than the existence of positive outcomes. This study drew on the challenge model of resilience, which anticipates a curvilinear relationship between stress exposure and adaptive functioning, to test whether adolescents reporting moderate levels of stress exposure were more likely to evidence prosocial behavior than youth exposed to more or less stress. Using data from approximately 13,000 adolescents, we tested three analytic models and investigated hypothesized moderation by coping, social resources, and markers of adolescent status. Our results did not align with the challenge model. Instead, we found that stress exposure was differentially associated with measures of prosocial behavior, that social resources supported volunteering but impeded helping a peer in some instances, and that markers of historically marginalized status were more predictive of stopping peer harassment than volunteering. Implications for future research are discussed.