In this paper, work with two adolescents from different families, each of whom lost their same-sex parent in tragic circumstances, is described. During the course of our work together, both adolescents became embroiled in delinquent activities and also drugs which led to their being sentenced to prison. The paper described our work prior to, during and after this period of imprisonment and the importance of a continuing professional network of which therapy was one part. The difficulty for these adolescents in finding and establishing an ‘inner authority’ was greatly affected by their experience of their parent's death, but their ability to identify with and make reparation to their surviving parent was a significant factor in their prognosis.