A long history of research has indicated that neighborhood poverty increases youth's risk taking and delinquency. This literature predominantly has treated neighborhoods as independent of their surroundings despite rapidly growing ecological evidence on the geographic clustering of crime that suggests otherwise. This study proposes that to understand neighborhood effects, investigating youth's wider surroundings holds theoretical and empirical value. By revisiting longitudinal data on more than 1500 low‐income youth who participated in the Moving to Opportunity (MTO) randomized intervention, this article explores the importance of extended neighborhoods (neighborhoods and surroundings) and different concentrated disadvantage configurations in shaping gender differences in risk taking and delinquency. The results from two‐stage, least‐squares analyses suggest that the extended neighborhoods matter and they matter differently by gender. Among girls, extended neighborhoods without concentrated disadvantage were associated with lower risk‐taking prevalence than extended neighborhoods with concentrated disadvantage. In contrast, among boys, localized concentration of disadvantage was associated with the highest prevalence of risk taking and delinquency. Interactions between the immediate and surrounding neighborhoods were similarly associated with differential opportunity and social disorganization mediators. Among the more critical potential mediators of the link between localized disadvantage and boys’ risk taking were delinquent network ties, strain, and perceived absence of legitimate opportunities for success.