This chapter aims to describe the process of working psychologically with young offenders in the community. It provides an overview of the Youth Offending Service (YOS) and the needs of the young people who come in to contact with it. A case study is detailed explaining the process of referral, assessment, and intervention with a young man involved with the YOS on a voluntary basis while awaiting trial and sentencing for a violent offence. Due to the case histories of young people who come in to contact with YOS, a trauma and attachment approach is often used, and this chapter explains this approach and its significance. A number of psychometric tools were used in the assessment including the Paulhus Deception Scale, the Wechsler Adult Intelligence Scale, Fourth Edition, and Beck inventories for anxiety and depression. A formulation of this young man’s offending was also provided to aid understanding in addition to the plan for psychological intervention alongside some future recommendations.