This dissertation uses a mixed methods approach to examine the stigmatization of children of incarcerated parents and its impact on educational experience. Prior research on educational disparities indicates that both psychological effects of stigma and teachers’ judgements can adversely impact academic outcomes. Scholars have also shown a correlation between school discipline and academic achievement. In this dissertation, the stigma of parental incarceration is explored along two dimensions – the experience of, and response to, stigmatization from the perspective of children who have experienced parental incarceration, and stigma from the perspective of teachers responding to classroom misbehavior. As illustrated through the accounts of children of incarcerated parents, the experience and the effects of stigmatization vary greatly between individuals and across contexts. One theme appearing frequently in these accounts and throughout the literature on parental incarceration is the impression that children of incarcerated parents are viewed as more prone to delinquency than their peers, due to the associative stigma of parental incarceration. This theme is further examined through a factorial survey of teachers, which reveals that teachers are more inclined to attribute the misbehavior of children with incarcerated parents to internal characteristics, living in a rough neighborhood, and chaos at home. While theory suggests that these attributions could contribute to differential treatment for children of incarcerated parents, the findings presented here do not suggest that teachers’ disciplinary decisions are affected by parental incarceration.