The origins of the right to health care are analyzed. The purpose is to establish the state of observance of the right of convicts and staff to health protection, to determine the main directions for improving legal regulation and organization of medical services in the criminal Executive practice of Ukraine. The methodological basis of the study is a dialectical method of scientific knowledge, which allows us to consider the observance of the right to health of prisoners and staff in prison in their development, relationship, and mutual influence. On this methodological basis, separate scientific methods of cognition are used. In particular, system-functional, structural-logical, as well as statistical and sociological research methods. The problems with the right to health protection in conditions of deprivation of liberty are outlined, namely, when serving sentences of imprisonment for a certain period and life imprisonment. It provides an overview of the problems in respect of the right to health protection, related to personnel who carry out sentences against convicted persons. Attention is drawn to the practical level and today's extremely low assessment of the work of medical institutions in places of detention: unsatisfactory pricing policy for medicines, outdated equipment, and lack of professional medical personnel. Proposals are made to ensure the rights of convicts to health care in places of detention in Ukraine.