This article presents two key findings from a case study on the impact of a theatre laboratory programme implemented at 'C. Beccaria' youth detention centre in Milan. First, the opening of a permanent theatre inside the prison, with the involvement of the broader community, has helped fulfil detained minors' rights to culture and rehabilitation, as well as remodel the relationship between prison and society. Second, the institution's reaction to the theatre laboratory has been ambivalent. The article critically examines this tension, exploring the conditions required to rethink and transform the institutional, rehabilitative, and cultural framework of the youth detention centre.