During the last two decades, security apparatuses from transitional states have become targets of either bilateral or multilateral externally-sponsored interventions often within the (normative) framework of security sector reform (SSR). SSR aims at establishing effective and efficient security provisions and establish respect for human rights, democracy, and the rule of law. Nevertheless it appears that prison reform is rarely identified as a high priority in SSR programmes. Moreover, contrary to police and justice reform, prison reform has received little scholarly attention in transitional societies. Building on the work of Murdoch (2013) on correction reform in Kosovo and qualitative interviews with Belgian prison officers and other prison personnel who have assisted prison reform in transitional societies, this research provides insights in different prison reform programmes. By including the perspectives of the practitioners, it seeks to contrast theory with praxis and hence to advance our knowledge on the objectives of prison reform, the way the reforms are introduced and implemented and the obstacles the ‘reformers’ are being confronted with.