I began my life as a prison theatre artist 25 years ago. Over the years, through first-hand experience with prisoners, their families, and others, I came to understand some of the more oppressive elements of the state prison system, and the relation of that system to the larger prison-industrial complex. This essay is a reflection on the key events and relationships that provoked me into critical awareness, engagement, and activism. I make the argument that a seemingly hyper-conservative prison theatre programme can in fact be an effective breeding ground for critical resistance and transformation.