The unrestrainable evolution of medical science and technology is drastically changing health-care, enabling new medical procedures and remedies, which are increasingly intertwined with moral principles. Although a uniform European approach on assisted suicide is lacking, a common trend is developing: the boundary between euthanasia, assisted suicide and end-of-life care and the frontiers of legitimate medicine are becoming increasingly blurred. In Italy, a ruling of the Constitutional Court, no. 242/2019, declared the partial unconstitutionality of article 580 of the Italian Criminal Code, which prohibited assistance in suicide. Specifically, article 580 excluded the criminal liability for the person who, in the manner provided for in Articles 1 and 2 of the law 22 December 2017, no. 219, “facilitates the execution of intention of suicide, autonomously and freely formed, of one person kept alive by life-sustaining treatments and suffering from an irreversible pathology, source of physical or psychological suffering that he/she deems intolerable, but fully capable of making free aware decisions, provided that such conditions and methods of execution have been verified by a public structure of the national health service, following the opinion of the territorially competent ethics committee.” The present paper analyzes the legal regime of assisted suicide in Italy, the role of the rule of law, and the crucial boundary between the branches of government with regard to this delicate issue, and investigates current legal challenges and potential future legal tracks.