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A long history of research indicates that neighborhood poverty increases male and female youth’s risk-taking and delinquency. A rapidly growing literature on the spatial ecology of crime suggests that neighborhood-level crime is affected not only by within-neighborhood poverty but also by poverty in the surrounding areas. Yet, the neighborhood effects literature continues to define neighborhoods as isolated islands, independent of the surroundings. The present study advances the case that there is theoretical and empirical value in considering the broader neighborhood environments to better understand how neighborhoods affect youth behavior. Re-examining longitudinal data on gender differences in risk-taking and delinquency by youth in the Moving to Opportunity (MTO) randomized intervention, analyses explore the role of extended neighborhoods (immediate neighborhoods of residence together with nearby surroundings) and different extended configurations of concentrated disadvantage. To understand the mediating factors underlying gender differences within extended neighborhoods, neighborhood measures derived from independent sources were matched to the residential history of MTO youth. The results suggest that the extended neighborhoods matter and they matter differently by gender. Among girls, extended neighborhoods without concentrated disadvantage were associated with a lower prevalence of risk-taking relative to extended neighborhoods of concentrated disadvantage, as expected. In contrast, localized concentration of disadvantage was associated with boys’ highest prevalence of risk-taking and delinquency. Boys’ delinquent ties, low collective efficacy, strain, and crime witnessing emerge as potential mediators of localized disadvantage effects within extended neighborhoods.