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Prior research suggests that criminal justice contact is associated with weakened social ties, a process termed interpersonal exclusion (Jacobsen, 2020). However, most studies assume that the stigma of such contact is experienced similarly across settings, overlooking contextual conditions that can either foster or mitigate stigma. This study posits that context can shape stigma by influencing the perceptibility (i.e., whether known to others) and discredibility (i.e., whether hurting one’s reputation) of criminal justice contact. To capture both dimensions, this study introduces novel measures of school cultural and structural context. Using longitudinal data from a school-based study with adolescent peer network information and employing stochastic actor-oriented models, this study examines how the cultural and structural contexts of grade cohorts influence adolescent friendship ties following police contact. It also assesses whether the main effects of police contact and the moderating effects of contextual factors vary between middle and high school due to contextual differences. Findings indicate that police contact weakens adolescent friendship ties in middle school but not in high school. Cultural norms around delinquent students’ popularity moderate this association in middle school, whereas structural features of network closure moderate this association in both middle and high school. These findings highlight the importance of school cultural and structural contexts in shaping the interpersonal consequences of police contact, revealing distinct patterns between middle and high school and their implications for the social inclusion of justice-involved youth.