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There is a longstanding debate in criminology about the competing roles of agency and context in the genesis of lawbreaking behavior. However, these are not mutually exclusive: agency can be conceptualized as intimately related to all aspects of one’s context, or situated. This paper describes the situated agency of young people in marginalized communities who engage in serious lawbreaking, taking into account the social harms that they both experience and cause. Data were collected using ethnographic interviews and neighborhood walks with fourteen young people. With a focus on neighborhood context and agency in lawbreaking behavior, interviews elicited participants’ histories, actions, perceptions, and experiences. Participants reported having engaged in a range of lawbreaking behaviors, mostly serious, predominantly related to violence, weapons, and drug sales. These acts were catalyzed by four overlapping categories of situations: peer pressure and the desire to fit in, the need or desire for money, family-related stress, and interpersonal conflicts. Study findings are consistent with prior scholarship, lend support to a number of interventions at multiple levels, and suggest that preventive programming should be individually tailored and varied. Additionally, situated agency contributes a valuable analytic tool for understanding agency and context in relation to each other.