The modern development of information technologies influences all spheres of human activity. The processes of digital transformation have affected, among other things, such a vital area as medicine. Medical care based on information technologies—telemedicine—is becoming increasingly common. The complex nature of the research object inevitably entails difficulties in its practical implementation, including in terms of legal regulation of the introduction of distance and information technologies in the process of providing medical care to patients. The Russian Federation is not the flagship of the practical application of telemedicine services; foreign countries have much more experience in this field. In this respect, the domestic legislation regulating healthcare issues is not without gaps and problems associated with the use of telemedicine technologies, and needs constant improvement, therefore, the purpose of this study is to identify these gaps in legislation and develop possible solutions to the problems of law enforcement in this area. This article discusses the barriers and opportunities for legal regulation of the use of information and distance technologies in the field of medical services. It also analyzes the current legislation in the field of telemedicine, including the prospects for the introduction of an experimental legal regime. The author has studied the experience of regulation of health service provision using information technologies in foreign countries. Within the framework of the study, an assessment of the effectiveness of the application of existing regulatory legal acts has been carried out and problems of their application have been identified. The study uses general scientific methods of logical cognition. In particular, the experience of a number of countries in the application of information technologies in the field of medical services is analyzed using methods of analysis and synthesis. The system method has made it possible to assess the key areas of improvement of Russian legislation in the field of telemedicine, as well as to develop recommendations for overcoming the main barriers of law enforcement. The formal legal method and the method of juridical hermeneutics have been used in the analysis of normative legal acts regulating the provision of telemedicine services in the Russian Federation and abroad.