Recent studies have found that race, work history, postprison employment, and recidivism are intertwined, suggesting that race and work history may shape the employment–recidivism relationship in nuanced, yet underexplored ways. Additionally, the literature has yet to settle on what kinds of employment patterns matter most for recidivism. These issues are especially important to resolve given contemporary concerns about mass incarceration and racial disparities among citizens returning from prison. To investigate these questions, we analyze administrative prison records, unemployment insurance (UI) quarterly data, and a recidivism follow-up documenting multiple failures for approximately eight years. Frailty models, which address unobserved heterogeneity among those prone to multiple recidivism events, reveal that establishing a recent work history unlocks the protective effect of employment, and that the relationship between postprison employment and recidivism does not vary by race. We also find that being sporadically employed is as protective as being more consistently employed. Our findings imply that employment contributes to racial disparities in recidivism via racialized barriers to labor market participation rather than via differential effects. Our results further suggest that addressing barriers to employment, especially for those with no work history and those facing racialized barriers to labor market entry, could significantly reduce recidivism.