Self-reported attachment characteristics, substance use and behavioural problems were assessed in 68 male juvenile delinquents from rural and urban areas. As was predicted, insecure attachment characteristics were related to behavioural problems, substance use, and poor family functioning. Urban delinquents reported more substance use and more interpersonal problems with peers and family members than their rural counterparts. Contextual influences on adolescent attachment relationships and adjustment problems may have implications for the administration and delivery of psychological treatments in youth correctional settings.