Truancy, disruptive behaviour and general disaffection from school are an on-going challenge in schools across the world, and it seems little headway has been made in developing effective strategies to support re-engagement. Many capable young people feel alienated from their schooling and seek affirmation and recognition via other avenues – avenues which do not always serve them well. Internationally, adolescent transgression and disenchantment remain intractable, with some evidence even suggesting negative behaviour is on the rise. This study spans research across two secondary schools in two countries, Australia and the United Kingdom, and explores how peer teaching Drama may help re-engage disengaged or disaffected adolescents, and documents two separate but related projects in each country. In the course of research for the first project i.e. how Drama might be used to teach Conflict management, it was noted that peer teaching as a strategy in itself seemed to have a marked impact on several young women who had hitherto seemed reserved or vaguely dissatisfied and disengaged in the classroom. Although my first project had its genesis as part of a large Action Research study, as I began to focus on the experiences of these three Year 11 girls, it became apparent that a closer analysis of the personal impact of peer teaching through Case Study might yield deeper understanding. Thus the second project was designed as a Case Study from the outset – an exploration into how peer teaching might support the reengagement of two disaffected Year 9 girls. The five young women who are the focus of my research ranged in attitude from being quietly disenchanted to actively challenging and disruptive in their behaviour within the school context; none would have put themselves forward for responsibility or, in the case of the challenging pupils, would have been trusted with responsibility by their teachers. There was however one area of the curriculum all the girls enjoyed, Drama, and this interest was able to be utilised in peer teaching. Both projects were designed to involve participants as collaborators, and encouraged these students to take responsibility for shaping, delivering and reflecting on their experiences as teachers. They were stakeholders in the learning of others, and this responsibility provided profound personal learning experiences for participants, and rich insight for me into some of the reasons that might lie behind the girls becoming disengaged and disaffected in school. The study suggests there is a strong link between democratic teaching and learning processes, risk and emotional engagement, and the contribution that constructive challenge can make. My findings indicate that the combination of these factors can generate the self-esteem and confidence necessary to transform the attitudes and behaviour of disaffected and disengaged female students. The research also clearly demonstrates that peer teaching is a potentially powerful strategy to utilise in support of positive change and, in wider terms, possibly one way the challenge of adolescent truancy and disaffection might be addressed.