This paper situates education as an integral component of the overall prison rehabilitation process. The article discusses how an educational practitioner's knowledge of attachment theory and masculinities can be utilized to develop a secure methodological teaching environment in the classroom of a prison education unit and create a space where transformative learning can take place. The link between attachment theory and the social and institutional composition of masculinities are considered for their influence on perceptions and concepts of the masculine self and masculine identity in general. The practitioner who is cognizant of these issues has the potential to develop secure methodological frameworks that focus on creating a nurturing learning environment that has the potential to provide students with a space to safely reflect, examine and potentially transform their learning experiences and thus their sense of self.