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This article extends the literature about how employers interpret jobseekers’ criminal records, and whether that affects their discretionary decision-making throughout the hiring process. Our argument is three-fold. First, prior research rarely uncovers employers’ overarching beliefs in second chances regarding hiring justice-impacted applicants. Second, despite a restrictive “fair chance act” policy, two-thirds of employers in our sample deliberately sought out criminal history information as part of their evaluation. Third, employers place greater emphasis on jobseeker qualifications and fit in the application stage, and then prioritize character assessment in both the interview and appeals stages. As part of their appraisal, they look for specific markers from candidates per hiring stage, including positive credentials (application and appeals stages) and impression management abilities (interview and appeals stages). Our data draw on 22 interviews with hiring decision-makers from diverse industry fields. By revealing employers’ interpretations and discretionary decision-making, these findings have practical and policy implications.