In this article the authors draw on their own experience and research in applied theatre in Kenya in order to reflect on challenges currently facing practitioners working in the country. In order to outline the range of challenges faced by practitioners, issues related to the wider landscapes of government and politics in Kenya are explored, alongside challenges inherent in the international development sector's use of applied theatre and Theatre for Development in Kenya, and the struggle that many theatre practitioners face in terms of the legitimacy of theatre in Kenyan society.