Juvenile justice institutions have been slow to adapt their practices to the developmental challenges of adolescence. Traditional probation, which impacts the vast majority of justice-involved youth, is one such institution considering the primary goal is ensuring youth’s compliance with probation terms rather than long-term prosocial change. To better engage youth, jurisdictions are increasingly using graduated response systems that utilize incentives to reinforce desired behaviors in both the short- and long-term. Yet, little is known about what motivates youth. The current study tested three research questions. The first explored what types of incentives would motivate youth to do well on probation. The second tested what parents believe would motivate youth and how it compared to what youth desire. The final question investigated if older youth desired monetary incentives less than younger youth. Youth most desired praise-based incentives followed by privilege-based incentives and monetary incentives. Further, parents’ perceptions aligned with youths’ perceptions. Overall, these findings highlighted praise may be more impactful than previously thought, and further exploration is needed to understand its effect. Privilege and monetary-based incentives could still prove motivational for youth, but to a lesser degree than previously thought.