The Czechoslovak prison system was at a crossroads after 1989. It was clear to every- one that it would have to be humanised and modernised, and also that a system would have to be set up to ensure respect for convicts’ basic human rights. This was an elaborate task, complicated especially by the fact that a successful reform depended on many factors, from human resources to the economy of the newly established state. The paper explores three topics. The first part outlines the key trends in the prison system in the last years of the Communist Party dictatorship. After that, the authors analyse the situation in the prison system during the so-called Velvet Revolution in 1989 and shortly afterwards. That time saw repeated riots in the prisons, the establishment of prisoner organisations as well as prison staff who were critical of the previous development of prison system, and the start of the process of ridding the prison staff of its most compromised officers. The third part describes the post-revolution transformation of the basic operational principles of the Czechoslovak prison system, which can be summarised as depoliticisation, demilitarisation and humanisation.