Transitions represent an important milestone for children and are experienced differentially. For some children, transitions represent a critical period that can have a long-term impact on their lives. This paper examines the socio-emotional aspects of the transition through an exploration of the findings derived from an evaluative case study of a group-work intervention to support children with Social, Emotional and Behavioural Needs across the Primary-Secondary transition, seen through the eyes of an adolescent boy and related stakeholders. The study took place in two local authorities in Scotland. The intervention is informed by the 'Teaching for Understanding Framework' (Project Zero, Harvard University) and 'Multiple Intelligence Theory.' The study examines the impact of the intervention on participating pupils, in the process exploring the variables that impacted on pupil progress both internal and external to the intervention. The findings highlight the importance of: building trustful and respectful relationships between adults and children; creating a safe environment in which children will be listened to and cared for; high quality pedagogy and continuity and progression across the transition; and understanding the complexity of factors which may impact on the transition for individual children, particularly for those who may be at greater risk across it.