Although future expectations are consistently linked to juvenile delinquency, whether or not these expectations change contingent on behavior remains unclear. In addition, few studies have considered the role an official arrest plays in changing the expectations an adolescent holds for his future. The current study (1) examines the reciprocal relations between self-reported delinquency and adolescent future expectations to graduate from college, to have a successful job or career, and to stay out of trouble with the law, and (2) evaluates the reciprocal relations between re-arrest and future expectations. To address these questions, a sample of 1,166 male juvenile offenders were recruited after their first arrest and followed for 12 months. We find partial support for our prediction that educational, occupational and behavioral expectations will influence behavior, but also that behavior will influence future expectations. In addition, our results suggest that re-arrest predicts changes in expectations for staying out of trouble, but has no effect on educational and occupational expectations.