The research aims to analyze the history and current state of the legal regulation of telemedicine in Russia and identify legal constraints hindering the development of telemedicine. This research explores the development of scholarly legal discourse on telemedicine regulation. It examines publications in the field and traces the evolution of the normative framework by analyzing both current and repealed regulatory acts related to telemedicine. The research also considers experimental legal regimes, policy concepts, and directives issued by public authorities. During the research, the author employed the formal-legal, historical, and prognostic methods. This research examines the historical development and current state of telemedicine regulation in Russia. It defines the concept of telemedicine and identifies key challenges in its legal regulation. The author analyzes the broad and narrow approaches to defining telemedicine, distinguishes between telemedicine and related phenomena that can be classified as digitalization of health care, and highlights the problems of contemporary legal regulation of telemedicine technologies. The author also discussed the prospects and risks of implementing artificial intelligence tools in telemedicine. Telemedicine technologies, which are among the areas designated for the creation of experimental legal regimes (regulatory sandboxes), are subject to traditional and innovative forms of legal regulation. The legal barriers hindering the development of telemedicine were identified.