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This project uses data from the Criminal Justice Administrative Records Systems linked with survey and administrative data sources from the U.S. Census Bureau to provide the first evidence on the looming retirement crisis stemming from the aging generations of Americans who have been increasingly impacted by criminal justice policies like mass incarceration. In this research, we (1) characterize the economic vulnerability of those with criminal histories approaching retirement, (2) measure the share of current retirees with criminal records and provide projections of how these rates among retiring cohorts will close to double over the next 20 years, and (3) leverage two recent class action lawsuits against the Social Security Administration to quantify how extending safety net assistance (financial support and health insurance) impacts this population in old age. This analysis shows that extending programs like OASDI and SSI to the aging justice-involved populations has a number of important benefits: reducing poverty; decreasing disability and mortality rates; lowering usage of costly living arrangements like nursing homes, homeless shelters, and residential treatment facilities; and strengthening co-residency among families.