Securing employment support remains elusive for most formerly incarcerated jobseekers, with the majority still unemployed years after their release-nearly five times the national average in the general population (Melhorn et al., 2024). Research indicates that these difficulties may arise from negative stereotypes about formerly incarcerated individuals' moral character and competence, limiting the job-search assistance they receive from others. Integrating theory and research on criminal stigma and impression formation processes, we suggest that disclosing their criminal history with (vs. without) individuating information about educational accomplishments and work experiences during incarceration can help jobseekers gain job-search assistance. We examine our conceptual model in three complementary studies: a preregistered audit experiment with state legislators (n = 4,894) and two experimental vignette studies (n = 491; n = 493). Our results contribute to the theory on the reputational implications of criminal records, impression management, and employment discrimination. Additionally, our findings have implications for policies and practices intended to promote successful reintegration. (PsycInfo Database Record (c) 2025 APA, all rights reserved).