Colectivo Sustento and Fénix & Ilusiones are two community theatre groups in Santiago, Chile. Inside and outside the Colina 1 men's prison on the outskirts of Santiago, they have developed a continuous 12 year experience that provokes critical reflection, agency and collective process, as resistance to the devastating impact of neo-liberalism. Using their recent theatre tour to juvenile detention centres as a starting point, this article journeys through the limitations, freedoms, challenges and successes of this community-based experience. This journey is a never-ending process towards increasing the concrete possibilities of being active agents for social change, even from within a prison; in this case, the voice of experience and the pretext of theatre are harnessed in order to communicate and affect the decisions of young offenders.