This article utilizes interviews with three teaching artists to interpret their lived experiences of teaching dance classes within New Zealand prisons. Prison environments and prison cultures create a multitude of challenges, such as the physical environment itself, social dynamics and hierarchy, and interaction and relationships with incarcerated participants. Through this discussion I seek to provide an insight into some aspects of the prison environment and prison culture. The article presents opportunities for considerations and suggestions that may assist teaching artists with navigating the challenges of teaching in an unfamiliar environment.