In this study we examine whether feelings of anticipated shame and anticipated guilt when being caught for an offence mediate the relationship between parental monitoring, bonds with parents and school, deviant peers, moral values and offending. We use data from the SPAN project, a study that collected detailed information about offending, moral emotions and socialization among 843 adolescents in The Hague, the Netherlands. The results show that moral emotions of both anticipated shame and guilt have a strong direct effect on offending. The results also show that the relationship between parental monitoring, deviant peers, moral values and offending is substantially mediated by anticipated shame and guilt. This study clearly suggests that both shame and guilt need to be included in the explanation of offending. © The Author(s) 2013.