Ex-prisoners’ recidivism risks are high. Several theories state that employment can reduce these risks but emphasize that the protective role of employment is conditional on job qualities (work intensity, job duration, etc.). Longitudinal research on the role of employment in ex-prisoners’ recidivism patterns is scarce, and most existing work used a simplistic employment measure (i.e., employed vs. unemployed), leaving the topic of job quality underexplored. This study examines the association between employment characteristics and recidivism among Dutch ex-prisoners. Using longitudinal data of the Prison Project (n = 714), we found that not just any job, but particularly stable employment and jobs with a higher occupational level could help reduce crime rates among these high-risk offenders. Many ex-prisoners face a human capital deficit that complicates the guidance to high-quality jobs. It might, however, be possible to help place ex-prisoners in stable employment.