Objective To examine factors associated with adolescent and parent-reported adherence to prescription and over-the-counter (OTC) medications in a cross-sectional sample of youth with inflammatory bowel disease (IBD). Method Ninety adolescents and their parents completed measures of medication adherence and disease, individual, and family factors while attending an outpatient gastroenterology appointment. Results Longer time since diagnosis, greater perceived disease severity, and a lack of autonomous motivation to adhere predicted adolescent report of lower adherence to prescription medications. Similarly, longer time since diagnosis predicted adolescent report of lower adherence to OTC medications. Less time since diagnosis, greater maternal involvement in the medical regimen, higher perceived disease severity, and less perceived conflict predicted better parent-reported adherence to OTC medications. Conclusions Interventions for improving adherence in adolescents with IBD should address disease, individual, and family factors with special attention given to adolescents who have been diagnosed longer.