Background: This research is based on the perspective of dignity according to Chochinov; thus, the life imprisonment of detainees is assimilated to a severe disease. Methods: Ten male prisoners were interviewed trough Chochinov’s Dignity Therapy, and the results were analysed using thematic analysis. Results: Two areas of thematic prevalence emerged, namely, value of freedom, self-consciousness and education and their failure in jail, and life sentence as annihilation of life meaning and of the values of generativity and family. Conclusions: Life imprisonment has been described in its negativity by several respondents as a punishment worse than the death penalty. It has been compared to death itself, to a terminal illness, to torture and to a pain that grows over the years, with the awareness that despite the passing of time, you will not have the opportunity to return to your loved one and to a free life. In fact, prisoners live out their condition within a space in which any value that gives meaning to life risks being destroyed.

(1) Background: The Italian Constitutional Court’s decision n. 99/2019 abolished the distinction between physical and psychological health care in the Italian prison system. However, this and other changes to the penitentiary system present challenges to prison staff, which may vary based on their roles and backgrounds; (2) Purpose: To create a process of dialogue and collaboration that include different points of view, needs, and proposals regarding mental health in prisons, this study collects and integrates the perspectives of 91 prison staff who work in various capacities in eight prisons in northeast Italy. (3) Methods: Each participant was involved in either a focus group or a semi-structured interview, and thematic analysis was used to process the resulting transcripts; (3) Results: Through this process, 10 themes were derived that highlight the difficulties of working with prisoners with psychiatric disorders or psychological distress, including lack of human and economic resources, lack of positive communication between prisoners and society and a sense of professional incompetency; (4) Conclusions: Based on these themes, the need for increased points of view, dialogue, and collaboration between prison professionals and between prison and society is discussed, and the current feasibility of treating psychiatric disorders in prison is considered.