This article argues that the intergenerational implications of mass incarceration have promoted the educational demobilization of primarily marginalized groups. Using the Howard B. Kaplan Multigenerational data set, this article makes clear temporal links between parental incarceration (G1T7) and educational outcomes into adolescence (G2T2) and emerging adulthood (G2T3). Intergenerational theories of strain and stigma are argued to be mechanisms in the transmission of reduced educational mobility. The findings of this study reveal that net of prior disadvantage adolescents who have a once incarcerated parent have significantly lower school performance, and have 58.2% lower odds of being happy in the school setting than their counterparts not experiencing parental incarceration. Further, into emerging adulthood those having a once incarcerated parent have significantly less educational attainment than their counterparts. Interactions between parental incarceration and race, as well as gender, are found to be non-significant suggesting the effect of parental incarceration does not vary by these terms. However, due to the disproportionate likelihood of experiencing incarceration for poor black and Latino males, the parental incarceration effect is more concentrated among this group. The need for restoration to these groups due to the intergenerational outcomes outlined in this study, even with an end of mass incarceration, is discussed.