Dorothy Heathcote’s work was centred on using drama to make learning meaningful and focused on things that ‘matter’. She developed models and approaches that encouraged teachers to structure purposeful and relevant learning experiences through careful planning, framing, enactment and reflection. One such strategy was that of Rolling Role. This model is less well known than others but Heathcote herself believed that it had great potential to be utilized through something like a website. The Water Reckoning project was therefore initiated to revisit and reconceptualise the Rolling Role model in the lead up to the Heathcote Reconsidered conference. The project aimed to explore the potential of Rolling Role for international collaboration using digital platforms. The resulting project involved five different student groups, their teachers and researchers responding to a common pre-text. This paper will focus mainly on the development of the dramatic context, pre-text and decisions regarding the use of digital technologies. It will identify key factors and considerations for planning and working with the Rolling Role.