Italian prisons are confronting a multitude of severe challenges that compromise the dignity and safety of inmates and place prison personnel under considerable strain. This study provides a comprehensive analysis of the critical state of healthcare and living conditions in prisons across the region of Friuli Venezia Giulia (FVG), with a particular focus on facilities like Trieste, Udine, Gorizia, Pordenone, and Tolmezzo, which are notably afflicted by overcrowding. Overcrowding rates in these prisons have soared to unprecedented levels; for instance, Trieste’s facilities are operating at 175% capacity. This paper uses updated and extensive data sources including reports from Antigone, Inside Carceri, RAI News, and other relevant publications to paint a detailed picture of the adverse impacts such as inadequate healthcare services, escalating suicide rates, and deteriorating working conditions for prison staff. In response to these pressing issues, the paper proposes a series of targeted reforms. These include the adoption of telemedicine to improve access to health services, the construction of new prison facilities to alleviate overcrowding, the enhancement of mental health services to address the high incidence of psychological distress among inmates, and comprehensive measures to improve the working conditions of prison personnel. The proposed reforms are aimed at transforming these facilities into more humane and functional environments, thereby aligning them more closely with international human rights standards.