Educational Drama pioneer, Dorothy Heathcote, worked in new and innovative ways which were, even in the progressive times in which she was working, considered against the grain. This chapter examines her practice as a pedagogy of resistance and goes onto explore how, with the use of technology, Drama Education students carry on this resistant practice in new and challenging contexts. \ud Heathcote's 'Rolling Role' model is explored by the students as a way of discovering their own resistant practice and re-discovering the freedom to learn for themselves and their pupils.