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This study used longitudinal data from 202 at-risk young men to examine effects of arrests, prior risk factors, and recent life circumstances on job loss across a 7-year period in early adulthood. Repeated failure-time continuous event-history analysis indicated that occurrence of job loss was primarily related to prior mental health problems, recent arrests, recent drug use, and recent being married/cohabitation. It is argued that long-term effects of criminal justice contact on employment outcomes should be understood in the context of (shared) prior risk factors and recent life circumstances.