This chapter presents research into staff experience at two rather different youth justice facilities one in England and the other in Australia. It explores the challenges of prison officer work with young males, aged 15-17 years old in an English young offender institution. The chapter analyses the way that the perceived 'pains' of prison officer work influenced staff's perceptions of child prisoners, the construction of institutional 'misconduct' and the willingness to use punitive measures to gain or maintain social order. It discusses the real challenges of working in a low trust and tense environment with limited opportunities for emotional expression or discharge. The chapter focuses on an Australian initiative for custodial staff working with young people in custody. It revisits the context which gave rise to this successful ongoing programme, its multi-theoretical underpinning and modus operandi. Thechapter explores with consideration of similarities and differences between these models of residential youth justice.