Research suggests that young children transgress conventional rules in every culture and society. In this article, the argument is made that rule teaching and learning provide insight into how children learn to be part of a group. The research question addressed is, "Why do some children transgress the rules if their actions risk jeopardising valued group membership?" A qualitative case study of a child who repeatedly challenged the rules in a child care setting is presented. Three vignettes are analysed and discussed. For the child, "rule learning" becomes a public rather than private affair and both the child's transgressions and the teacher's responses are under group scrutiny. Teaching young children to feel a sense of responsibility and remorse for transgressions is not easy and it takes teachers into family territory making it one of the more contentious aspects of early childhood educational practice. Sociocultural theory provides a means to reframe children's challenging behaviours as adaptive responses to their environment when they are overloaded or uncertain as to how to manage group demands. Ideas for how to help children navigate between individual needs and group demands are discussed.