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We explore alternative approaches to understanding the contextual influence of neighborhood racial composition on risk behavior (violence, delinquency, substance use) among Black urban youth. The racial isolation perspective argues that Black-segregated neighborhood exposure increases time spent in concentrated poverty neighborhoods with limited access to “mainstream” institutions and influence for Black youth. In turn, rates of risk behavior are expected to increase with exposure to racially isolated activity spaces. Alternatively, Black youth may spend a substantial amount of time in low proportion Black neighborhoods as youth and their families seek organizationally-based resources that are typically less available in segregated areas. Although these exposures increase access to resources, they may also exacerbate strain due to racialized interactions in white spaces, increasing the likelihood of risk behavior by comparison with Black youth who maintain high levels of exposure to same-race dominated spaces. We employ unique survey, ecological momentary assessment (EMA), and GPS data on youth ages 11-17 from the Columbus, OH-based Adolescent Health and Development in Context study to test hypotheses regarding the association between exposures to neighborhood racial composition in activity spaces and individual level self-reports of risk behavior. Findings indicate that higher levels of exposure to low proportion Black neighborhoods among Black male youth are positively associated with both last-30-day violence and delinquency reports on in-home surveys as well as in-the-moment risk behavior reports from ecological momentary assessment. We discuss the implications of these findings for contemporary neighborhood theory as well as the validity of risk behavior reports derived from EMA.