This study sought to explore potential mechanisms through which uncontrollable, chronic stressors may lead to hopelessness in low-income, urban adolescents. In particular, the roles of specific coping strategies as moderators and/or mediators of the association between stressors and hopelessness were examined. Results suggest that chronic, uncontrollable stressors were significantly and positively related to hopelessness in this sample. Active coping, distraction coping, and social-support-seeking coping emerged as moderators for males, such that uncontrollable stressors were more highly associated with hopelessness for those boys who reported using more active, distraction, and social-support-seeking coping strategies. An analogous moderating effect was found for ruminative coping for girls. Ruminative coping also emerged as a mediator of the relation between uncontrollable stressors and hopelessness for girls.