Adolescents' emotions in the context of moral decision-making repeatedly have been shown to predict actual behaviour. However, little systematic information on developmental change regarding these emotion expectancies has been available thus far. This longitudinal study investigated anticipated moral emotions and decision-making between the ages of 15 and 21 in a representative sample of Swiss adolescents (N = 1,258; 54 % female; M = 15.30 years). Anticipated moral emotions and decision-making were assessed through a semi-structured interview procedure. Using Bernoulli hierarchical linear modeling, it was found that positive feelings after a moral transgression (i.e., "happy victimizer" responses) decreased over time, whereas positive feelings after a moral decision (i.e., "happy moralist" responses) increased. However, this pattern was contingent upon the moral scenario presented. Systematic relationships between anticipated moral emotions and moral personality characteristics of sympathy, conscientiousness, and agreeableness were found, even when controlling for socio-demographic characteristics and cognitive ability. Overall, this study demonstrates that the development of anticipated moral emotions is not limited to childhood. Furthermore, our findings suggest that moral emotions serve as an important link between moral personality development and decision-making processes that are more proximal to everyday moral behavior.