Especially in oncology and in critical care, the provision of medical care can require therapeutic choices that could go beyond the patient’s will or intentions of the protection of his health, with the possible adoption of medical behaviors interpreted as unreasonable obstinacy or, at the opposite extreme, as euthanasia. In some cases, the demand for obstinate therapeutic services could come from the patient or from his relatives, in which case the dilemma arises for the health professional between rejecting such a request, in respect of their professional autonomy, or abiding by it for fear of a professional care responsibility for therapeutic abandonment. We analyzed and commented on emblematic clinical cases brought to court for alleged wrong medical conduct due to breach of the prohibition of unreasonable obstinacy. In healthcare it is impossible to fix a general rule defining any therapeutic act as appropriate, because on one hand there are technical assessments of medical competence, and on the other the perception of the patient and of his family members of the usefulness of the health care provided, which may be in contrast. The medical act cannot make treatments that are inappropriate for the needs of care or even be unreasonable; conversely, before the request by the patient or by his family members for disproportionate health services in relation to the results they may give in practice, in compliance with the legislative and deontological provisions, the doctor can refuse them, thus safeguarding both his decision-making autonomy and, therefore, his professional dignity.