This chapter looks at the male prisoner's working identity and examine its implications for performances of masculinity both in and out of the prison. The limited work prospects offered to prisoners during their incarceration mean that men may have to take on roles that subvert the gender norms or infantilise them through a lack of complexity or challenge, yet at the same time the holding of these positions of employment can result in a greater degree of masculine control and freedom in their otherwise highly controlled lives. The chapter derives from a piece of doctoral research under the title 'Men Inside: Masculinity and the Adult Male Prison Experience', funded by the University of Sheffield. It examines this intersection by looking in more detail at men's masculine identities through the lens of the world of work, and it considers the implications this intersection has for incarcerated men.