While previous research has examined the school-to-work transition of noncollege-bound youth, most have considered how a limited set of variables relate to job attainment at a single point in time. This exploratory study extended beyond the identification of constructs associated with obtaining a job to investigate how several factors, collected longitudinally in adolescence, related to employment stability and job quality with a diverse, nationally representative sample of non-college-bound youth. Logistic regression and structural equation modeling were used to determine the predictors of an adaptive school-to-work transition over time. Depression, substance use, adolescent educational attainment, and employment in adolescence were associated positively with obtaining employment. Adolescent educational attainment and employment in adolescence were associated positively with stability of employment. Depression, adolescent educational attainment, employment in adolescence, and income were positively associated with job quality. Substance use and parental education level were negatively associated with job quality. (Contains 1 figure and 2 tables.)