Reducing adolescent substance use is important in South Africa, a developing nation with increasing adolescent substance use, lack of leisure/recreation opportunities, and high rates of adolescent discretionary time. Previous research suggests leisure boredom and adolescent substance use co-occur in this setting. Using longitudinal data from 2,580 SA adolescents as they progressed from the 8th to 11th grade, the current study disentangles the associations of trait and state leisure boredom with substance use, and examines how ability to restructure boring situations moderates those associations. On average, individuals with higher trait boredom used more substances, and on occasions when state boredom was high, the prototypical adolescent used more substances. Although restructuring did not moderate these associations, greater ability was associated with lower substance use independent of leisure boredom. Findings illustrated the importance of considering how trait and state aspects of leisure may contribute to adolescents’ risk behavior and addressed through preventive intervention.