Building on Maguire (Male, failed and jailed: masculinities and the ‘revolving door’ imprisonment in the UK. Palgrave Macmillan, London, 2021) and Irwin (The felon. Prentice-Hall, Englewood Cliffs, 1970), this chapter focuses on the formative lessons people learnt when they were imprisoned as children or young adults, and how these experiences ease the transition to adult prisons. Specifically, it focuses on how the young men were ‘learning to graft,’ ‘learning to fight and survive,’ and ‘learning to play the system’ or ‘keep their head down.’ In so doing, this chapter illustrates how functional and adaptive prison victimisation can be, and how ill-equipped YOIs are to support young people or promote desistance. Rather than making a case for the abolition of YOIs for young adult men, and in keeping with the Gladstone principles, it is argued that deliberate and sustained investment in dedicated facilities and provision is needed.