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This article examines adult outcomes of previously institutionalized youths. The sample consists of 251 boys and girls who were institutionalized in a Dutch juvenile justice institution in the 1990s. Information on personal and childhood characteristics was extracted from the treatment files that were compiled during their stay in the institution. In addition, conviction data was used to determine subjects’ criminal careers from age 12 up to the year 2011. Conducting face-to-face interviews with these former JJI-detainees between 2010 and 2012 when they were on average 34 years old, we collected retrospective information on employment history and several important current life course outcomes, such as housing, employment, intimate relationships, parenthood, and health. This enabled us to examine effects of adolescents’ personal and background characteristics as well as their criminal and employment careers on current adult life adjustment. Results showed that these formerly institutionalized youths experience difficulties adjusting to conventional adult life. Moreover, while personal and childhood characteristics exert no significant influence on adult outcomes, criminal behavior in young adulthood is associated with a significantly lower level of later adult life adjustment, and employment in young adulthood is related to higher levels of adjustment in later adult life domains.