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Research has argued that children of incarcerated parents do not fare as well as their counterparts in the education system. Using the Howard B. Kaplan multigenerational data set of parents linked to adolescents (13-18), this research article proposes possible mechanisms by which this is occurring. Utilizing propensity score matching methods I compare the outcomes of children of incarcerated parents to children who have not experienced parental incarceration (N=132). Logistic and linear regression models are predicted on the matched samples. Findings reveal that on the individual level, children of incarcerated parents have more trouble concentrating and are less happy in school, and have lower educational aspirations than their counterparts, on the group level, they are more likely to share bonds with at-risk peers, such as those who use drugs and alcohol, and on the structural level, children of incarcerated parents are significantly more likely to live in areas of neighborhood disadvantage. The findings of this study suggest that children of incarcerated parents experience multiple forms of disadvantage that present this group as at-risk.