In many settings, including schools and other community settings, an increasing number of individuals are identified with relatively weak self-regulation. This article describes an apprenticeship approach to serving children, adolescents and adults with self-regulation problems. The approach highlights antecedent supports for successful participation in meaningful activities and interactive procedures designed to equip the individual with the tools needed to regulate behaviour and emotions in a strategic and successful manner. This approach is consistent with Vygotskyan developmental and pedagogical theories as well as the theory and practice of Positive Behaviour Interventions and Supports in behavioural psychology. The article ends with the presentation of a mosaic of evidence supportive of this approach.