This chapter examines ways of deterring serious and chronic offenders based on evidence from the Pathways to Desistance Study, which addresses the issue of perceptions of deterrence and looks into the mechanisms of deterrence for serious offenders. After a brief overview of the Pathways study, the chapter reviews empirical evidence that demonstrates the rationality of high-risk adolescents regarding involvement in crime. It argues that offenders take into account rational-choice perceptions in their offending decisions and goes on to discuss the elasticity and malleability of these perceptions, and whether adolescent offenders act differently when they change risk and cost perceptions. It also considers policy efforts aimed at maximizing deterrence among adolescent offenders and concludes by outlining future directions for theory and research