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While many studies focused on the weak labor market attachment of offenders, little attention is paid to the fact that many of them accumulated work experience before they came into contact with the criminal justice system. This motivates an examination of whether those who were employed at the time of arrest are able to hold down this job, especially because previous work showed that not the guidance to any job, but to stable employment helps to lower rearrest risks. Longitudinal data from the National Longitudinal Study of Youth (1997 – 2012) were analyzed to examine to what extent criminal justice contact puts employees in search for a new job, and how old versus new jobs (e.g., familiar versus new work environments) affect future arrests. To connect to prior work in which the moderating role of age in work-effects was emphasized, attention is paid to whether younger or older offenders benefit differently from holding down their jobs.