This report identifies factors that predict whether youth served by the Department of Social and Health Services (DSHS) or the Health Care Authority (HCA) become disengaged from school and work during late adolescence or young adulthood. Using a predictive modeling event history approach we find that childhood family and social risk factors, including poverty, homelessness, and behavioral health conditions influence the risk of later disengagement. Further, school measures were significantly predictive of disengagement risk, most notably participating in special education or English language learner programs during high school. Youth who experienced homelessness or criminal justice involvement in late adolescence or early adulthood, and those who become parents were also at increased risk of disengagement. Finally, our analysis indicated that youth are most at risk of disengagement upon leaving high school (with or without a diploma) and that youth with work experience are much less likely to disengage.