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Punishment avoidance, defined as breaking rules without receiving formal sanctions, is an understudied yet critical dimension for understanding inequalities in disciplinary outcomes. While extensive studies have examined why disadvantaged youth are more likely to be punished, less is known about how others avoid punishment despite rule-breaking behaviors. This study extends prior research by examining the role of parental involvement in shaping punishment avoidance in school discipline. Parental involvement in school, a well-documented form of social capital, has been shown to influence educators’ perception of and rule enforcement on children. Using survey and interview data from the Future of Families and Child Wellbeing Study, this project examines: (1) whether parental involvement (both general involvement in school activities and specific involvement in response to behavioral problems) is associated with the likelihood of suspension or expulsion; (2) to what extent these associations vary by parental proactivity (i.e., involvement initiated by the parent or the school); and (3) the strategies parents use to engage with schools and prevent disciplinary actions. By identifying mechanisms of punishment avoidance, this study suggests that inequalities in punishment are not only produced through bias against disadvantaged groups but also sustained through strategic use of social capital by advantaged groups.