This study explored potential barriers to sustaining recovery from substance use disorders (SUD) in adolescence, particularly for youth enrolled in school-based recovery programs, or recovery schools. Participants (N = 28) enrolled full-time in a Massachusetts recovery high school completed a survey of demographic information and scales assessing social desirability, parent and peer influence, and stigma. Results indicated that peers have slightly higher influence than parents, particularly among girls and adolescents with non-parental guardians. Participants living with parents who use substances reported being sober an average of 28.7 months, versus 40.9 months for those living with non-using parents. Participants with parental guardians also reported experiencing significantly greater social desirability when there is no family history of substance abuse.