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Formal equality and judicial neutrality can lead to substantive inequality for women and children, with social costs that extend beyond individuals and families and spill over into the larger social settings in which they are located. We consider the uniquely damaging effects of an “equality with a vengeance” (Chesney-Lind & Pollack 1995) that resulted from “tough on crime” policies and the 1980s federal and state sentencing guidelines that led to the incarceration of more women and mothers. We argue that legal equality norms of the kind embedded in the enforcement of sentencing guidelines can mask and punish differences in gendered role expectations. Paradoxically, although fathers are incarcerated in much greater numbers than are mothers, the effect threshold is lower and the scale of effect on educational outcomes tends to be greater for maternal incarceration. We demonstrate both student- and school-level effects of maternal incarceration: the damaging effects not only affect the children of imprisoned mothers but also spill over to children of nonincarcerated mothers in schools with elevated levels of maternal incarceration. We find a 15 percent reduction in college graduation rates in schools where as few as 10 percent of other students' mothers are incarcerated. The effects for imprisoned fathers are also notable, especially at the school level. Schools with higher father incarceration rates (25 percent) have college graduation rates as much as 50 percent lower than those of other schools. The effects of imprisoned mothers are particularly notable at the student level (i.e., with few children of imprisoned mothers graduating from college), while maternal imprisonment effects are found at both student and school levels across the three measured outcomes. We demonstrate these effects in a large, nationally representative longitudinal study of American children from the 1990s prison generation who were tracked into early adulthood.