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This article uses mixed methods to examine what factors shape the endurance of neighborhood poverty across generations. We focus on how parents’ economic and social characteristics and exposure to various neighborhood contexts contribute to the types of neighborhoods their children end up in as young adults. We also explore whether these parental characteristics are enhanced or replaced by the receipt of a housing voucher through the Moving to Opportunity (MTO) program—does an intervention providing families with additional resources to exit neighborhoods of concentrated poverty alter the intergenerational transmission of neighborhood poverty? Analyzing survey and interview data from the Baltimore MTO sample from 1995 to 2010, we find that children whose parents had more economic resources live in lower-poverty neighborhoods as young adults. Housing vouchers seem to substitute for these resources—they reduce the intergenerational transmission of neighborhood poverty only when children grow up in very low-resource families. Second, for children whose parents ever lived in a more advantaged neighborhood, housing vouchers seem particularly helpful in facilitating the move to lower-poverty neighborhoods, providing critical resources to achieve neighborhood aspirations. Third, ties to extended family in high-poverty neighborhoods increases the odds that young adults continuously live in or return to disadvantaged neighborhoods like those in which they grew up. Fourth, parental substance abuse is a key factor in perpetuating the intergenerational transmission of neighborhood poverty, as it limits children’s educational and occupational opportunities and leads to housing instability, reducing the odds that they move to lower-poverty neighborhoods as young adults.