Introduction Well begun is half done (Dutch proverb). Juveniles who were placed in detention or residential treatment centers for behavioral and/or emotional problems are less successful as adults across various life domains, such as education, work, income, and mental health (e.g., Culhane et al. 2011; Van der Molen et al. 2013). They also have an increased risk of being incarcerated in later life (Aizer and Doyle 2013; Petitclerc et al. 2013). Nonetheless, we know from existing research that not all high-risk adolescents end up in prison as adults. So which factors determine within this high-risk group who succeeds in the transition to adulthood; and, among those who fall behind, are their potential pathways to prison gendered? From a life course perspective, adolescence is an extremely important phase between child-and adulthood in which many identity and behavioral changes occur (e.g., Wenar and Kerig 2000). Increased flexibility in the behavioral and emotional repertoire during (early) adolescence enables adaptation to changing environmental influences during the development into adulthood (e.g., Granic et al. 2003). However, adolescents who are institutionalized in juvenile detention and/or treatment centers often experience less than optimal caregiving environments from early infancy into early adolescence. These boys and girls report high rates of childhood victimization (e.g., Belknap and Holsinger 2006; Silvern and Griese 2012), family violence (Abram et al. 2013), parental psychopathology (Bauer et al. 2011), and instability in caregiving situations (Price and Kunz 2003). Outside of the family environment, they often have additional difficulties in school where they have to repeat classes, are expelled or play truant (e.g., Henry et al. 2012). Responses to childhood difficulties-such as running away from home and early drug or alcohol use-contribute to their admission or sentencing to juvenile detention and/or treatment centers. Across sexes these experiences have been shown to be risk factors for serious and chronic offending (Johansson and Kempf-Leonard 2009).