This book presents research and practice which revitalises Heathcotes Rolling Role, an innovative trans-disciplinary model which connects the work of multiple classes to engage in collaborative imaginative work. The original model was developed by legendary teacher Dorothy Heathcote, an educational innovator who gained international fame for her transformational work centred on dramatic framing to activate meaningful and important learning. She developed models that encouraged teachers to curate powerful learning experiences through careful planning, framing, enactment and reflection. Teacher-in-Role and Mantle of the Expert are the most well known of her strategies, approaches where the teacher exercises high selectivity in a range of meditational tools and means, so as to empower students as agents with the power to act. While the Rolling Role model is less well known, Heathcote herself believed that it had great potential to be realised through using websites and digital technologies. In the wake of her passing and ongoing examinations of her legacy, a practical exploration was initiated to reconceptualise the Rolling Role model through the use of digital platforms. The resulting project, The Water Reckoning, was an international project which engaged students in exploring ideas related to climate change, water-based catastrophe and human resilience. Further analysis and archival research have informed a deeper understanding of key principles for implementing Rolling Role and its potential for global collaboration and learning. This work has included close analysis of a set of 16 videotapes Heathcote created as a set of consultations for teachers. The book therefore collects together for the first time accounts regarding the historical development of the Rolling Role system, examples of its use and reflections on its application through the use of digital technologies. Rolling Role has the potential to be applied in a wide range of educational contexts with its focus on engaged learning, and learning that matters.