In this retrospective longitudinal study we examined which characteristics of 114 Dutch adolescents, aged 12–18 years, and their environment, predicted (un)successful completion of a non-residential alternative educational program for adolescents with complex problems, who are at risk for school drop-out or residential placement. The adolescents received care and education in a non-residential alternative educational facility (School2Care) for a mean period of 9.6 months (SD = 5.5 months). 69% successfully completed the program, and 31% unsuccessfully completed the program, ending in residential placement or living at home without school attendance, work or internship. Case file analyses showed that younger age, disruptive behavior disorder and one-parent families predicted unsuccessful program completion. It should therefore be examined whether the alternative educational program can be improved to better meet the needs of younger adolescents, adolescents with disruptive behavior disorder, and from one-parent families.