Individuals with felony and misdemeanor convictions experience diminished opportunities to vote, obtain employment, and access student loans, housing, and public benefits. These consequences are compounded by race, gender specific circumstances, and low educational achievement, with Black felons, women, and persons with less education experiencing additional impediments to employment. Age also affects the likelihood of desistance from crime. Research shows that record clearance may enhance ex-offenders’ efforts to gain legal employment and enable them to fulfill family duties. However, past research has overlooked whether structural factors such as race, class, gender, age, and education impact reintegration efforts after record clearance. Utilizing 40 semi-structured interviews with a diverse sample of persons who completed or were in the process of record clearance, this study explores how demographic characteristics and personal histories influence ex-offenders’ motivations to desist, the new identities they seek to adopt, and their success at desistance and reintegration after record expungement. Our findings have important policy implications, since successful prisoner rehabilitation programs must be compatible with offenders’ specific needs and risks.