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Individuals with disabilities and people with a history of justice involvement each face significant barriers to employment. There is also considerable overlap between these groups: two-thirds of individuals in federal or state prison report at least one disability (Bixby et al., 2022; Wang, 2022). While a handful of studies descriptively highlight how justice-involved individuals with disabilities (JIID) face compounded labor market disadvantage, often shaped by race and gender, no study, to our knowledge, has sought to estimate this disadvantage quantitatively. This lack of quantitative evidence is partly due to the limited availability of publicly accessible datasets that consistently and reliably capture all three measures simultaneously: disability, justice involvement, and employment. Publicly available data sets that do contain all three measures have limitations related to how disability and justice involvement are defined and screened. Our paper addresses this gap by analyzing two national datasets—the Rehabilitation Services Administration Case Service Report (RSA-911) and the National Survey on Drug Use and Health (NSDUH)—to estimate employment rates of JIID and non-JIID individuals, stratified by race and gender. Findings suggest that, regardless of the dataset used, JIID has lower employment rates than their disabled peers without justice involvement—a pattern consistent across most gender-race subgroups. However, surprisingly, this trend is reversed for Black men with disabilities, with JIID having higher employment rates than their non-JIID counterparts. These findings underscore the need for intersectional research and targeted policies that consider subgroup differences, rather than treating JIID as a monolithic group.