This article explores prison work and the complex relationship it reveals between money, confinement, and carceral capitalism. Drawing on ethnographic research conducted in a private prison in the UK, we argue that confinement exacerbates prisoners’ obsession with money and predatory entrepreneurialism. Using data co-created with prisoners, we demonstrate how this obsession with money reinforces the prison-industrial complex and reflects the broader dynamics of carceral capitalism. Furthermore, we illustrate how prison work perpetuates neoliberal exploitation, surveillance, and control, ultimately hindering rehabilitation and societal reintegration. Our analysis underscores the need for a comprehensive reassessment of the prison-industrial complex. We conclude that rather than viewing prisoners as a captive audience for reproducing carceral capitalism, prisons should be reimagined to prioritise the humanity of those impacted by the criminal justice system and to create alternative models of accountability and social transformation.