This research is an extensive comparison of two maximum-security prisons in England. Its key aim was to describe the contemporary experience of prisons ‘at the deep end’ of an expanding and deepening penal system. In part, this research revisits and builds on the work of Sparks, Bottoms, and Hay (1996) in Prisons and the Problem of Order, but does so in light of contemporary penelogical developments. It also draws extensively from the work of Leibling (2004) on quality of prison life, but applies her work at the extreme end of imprisonment. This research takes into account both the contemporary and historical context of the two prisons studied. The historical aspect of the research included the study of available documents and interviews with key figures from each prison’s past. The current experience of staff and prisoners in the two prisons studied was investigated primarily using an ethnographic approach. Three months were spent in each prison, interviewing staff and prisoners and observing prison life. In addition, survey data was collected from staff and prisoners at each prison using a revised version of the Measuring Quality of Prison Life survey (Liebling and Arnold 2002). The research found that the repressive environments appeared to outweigh the potential benefits of any rehabilitative opportunities. Although these prisons were quite effective in delivering punishment to prisoners, the more constructive purposes of imprisonment were lacking. Current penal policy in the UK is increasingly punitive and the use of prison sentences and their increasing length means that it is now more important than ever (e.g. in view of the European convention on Human Rights) to keep a close watch on the conditions in which prisoners are spending these sentences.