Drawing on an amended version of a survey employed in three previous studies, this article reports the problems experienced by 294 male prisoners serving very long life sentences received when aged 25 or under. The broad findings are consistent with previous work, including few differences being found between the problems experienced as most and least severe by prisoners at different sentence stages. By grouping the problems into conceptual dimensions, and by drawing on interviews conducted with 126 male prisoners, we seek to provide a more nuanced analysis of this pattern. We argue that, while earlier scholars concluded that the effects of long-term confinement were not ‘cumulative’ and ‘deleterious’, adaptation to long-term imprisonment has a deep and profound impact on the prisoner, so that the process of coping leads to fundamental changes in the self, which go far beyond the attitudinal.