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Researchers at Northwestern University are examining the impact of incarceration history on life-course achievements of delinquent youth, up to median age 32. The Northwestern Juvenile Project is a prospective longitudinal study of 1,829 youth (1172 males and 657 females) who were detained in the juvenile justice system between 1995 and 1998. Using correctional records and self-reported data from our 16-year follow-up interview, we explored the association between incarceration exposure (juvenile detention, adult jail, or prison) and life-course achievements. Participants who had been incarcerated in prison one or more times during the 16-year follow-up had fewer positive outcomes than those who had been incarcerated only in juvenile facilities. Socioeconomic outcomes like education, housing, and gainful activity (employment or school) were the most affected. Male participants incarcerated only in juvenile facilities had 5.2 times the odds of engaging in gainful activity than male participants who had been in prison (95% CI, 1.9-13.9), and 3.6 times the odds of male participants who had been in jail (95% CI, 1.2-10.7). Persons with greater exposure to the correctional system struggle to attain basic, normative milestones during adulthood. The justice systems - juvenile and adult - must expand alternatives to incarceration and enhance reentry services.