The purpose of this study is to investigate the well-being of female inmates in Italian prisons. The hypothesis is that stress in women prisoners is strictly related both to “external” networks and “internal” support, and is more linked to the feeling of loneliness than to coping with the difficulties of prison life. Qualitative study involving adult female prisoners in the prisons of three Italian regions (Campania, Lazio, Emilia Romagna). 37 individual semi-structured interviews were conducted. The interviews were processed using the CAQDAS contents (Computer Assisted/Aided Qualitative Data Analysis Software) by the software Atlas.ti, to practice the Grounded Analysis method to attain the construction of categories and its relations. The interviews show multiple levels of reflection, crossbreeding mainly two plans: a situational one and a personal one. The main dimensions emerged are: the access to activities in prison (work, projects, sociality) experienced as a deterrent to depression and as an opportunity for the future reintegration into the “free” society; the motherhood, as a spur to a resilience, but also in reference to the difficulties associated with the conditions of segregation. The main theme that crossed all the conversations is the loneliness lived as a prison disease. More attention should be given to the re-socialization aspect of prisons, constructing new ways to guarantee the prisoners a valid alternative to deviant behaviours so as to help restore family relationships and the reintegration in society.