In order to contribute to research into youth crime prevention, the current study aimed to explore the experiences of children in conflict with the law prior to receiving their first caution or conviction. Participants were recruited at a Youth Justice Service and included five children working with the service, their five case managers, and two of their parents/guardians. Data was collected using semi-structured interviews and timelines were used to support the children in sharing their experiences. Data was analysed using Interpretative Phenomenological Analysis, which focuses on understanding how individuals experience the world and how they make sense of those experiences. Six group experiential themes were identified within the analysis. These consider the events leading up to offending and whether it could have been predicted, the extent to which the children felt supported, the effect of school practices, the impact of peer influences, difficulties with managing emotions, and the children’s readiness for change. Each theme is discussed and recommendations for practice and future research are considered. The importance of placing children’s experiences at the forefront of research is highlighted throughout.