In this article, we employ Spencer's (1995) Phenomenological variant of ecological systems theory (PVEST) as a framework to examine risk and resilience, with a specific focus on understanding hypermasculine attitudes among low-resource urban, adolescent males. In the article, we highlight the need to understand normative human development processes in context and to consider risk and resilience in conjunction with these processes. We describe findings from a study of risk, social supports, and hypermasculinity. In the discussion, we outline the implications of these findings for theory and practice.