An entirely different approach is needed regarding the way in which troubled learners are perceived and approached. The removal of traditional punitive methods has left many educators unequipped for youth showing destructive behavior. This article reviews the shift towards a restorative approach within education in the Western Cape, South Africa. The Western Cape Education Department (WCED) manages 1,459 public schools serving nearly a million learners (WCED 2004 Annual Survey). There is an urgent need to look at effective strategies for dealing with challenging behaviour. Educational progress required addressing conditions that interfere with teaching and learning. Efforts should focus on creating a culture of teaching and learning that promotes academic excellence, positive socialization, responsible citizenship, and healthy lifestyles. The school can serve as an ideal setting to reclaim or redirect at-risk learners away from self-defeating and destructive outcomes. The Circle of Courage Model calls for creating opportunities for young people to experience Belonging, Mastery, Independence, and Generosity (Brendtro, Brokenleg, & Van Bockern, 2002). These universal values provide the foundation for developing resilience and self-worth. Schools have an important role to play in teaching young people to replace harmful behaviour with positive action, which may be their first formalized contact with justice and injustice. Strategies designed to encourage prosocial growth emphasize caring for others and experiencing care. Educators and support staff in direct contact with the young person and the family need basic knowledge and skills to enable them to work in the life space of young people in distress. By changing crises into learning opportunities, troubled young people can learn positive lessons from their problem behaviour. Response Ability Pathways (RAP) training provides basic skills for establishing positive relationships and effective communication based on trust, respect, and understanding between educators and young people presenting challenging behaviour. Both the Circle of Courage and RAP are relevant to all five levels of the support model for young people at risk developed by the WCED (2001). The strategy for encouraging positive behaviour in schools in the Western Cape is based on: (a) promoting reclaiming environments; (b) introducing a strength-based, developmental, and restorative approach in dealing with challenging behaviour; and (c) building the capacity of educators to ensure quality and effective services and education for children and young people in distress.