As covid-19 rips through the European countries, the fragile Italian penitentiary system reveals its deepest weaknesses. Indeed, although ensuring social distancing and maintaining adequate sanitary conditions in detention has been a worldwide major challenge, Italy’s situation has proved arguably more dramatic. National penal institutions have always struggled with endemic overcrowding issues, with a rate of occupancy still averaging 119,4% in 2020. In this precarious scenario, severe precautionary measures have been promptly undertaken to guarantee prisoners’ fundamental right to health care. Taking the cue from this emergency response framework, it will be examined the effectiveness and the proportionality of these normative solutions. Also, the long-term impact of this exceptional approach will be highlighted, by considering if it may represent a valuable starting point to overcome structural inefficiencies and improve constitutional guarantees of prison inmates.