The article provides a comparative analysis of the regulatory and legal regulation for the processing of a special category of personal health data in the European Union and in the Russian Federation in regard to the digitalization of national health systems. Special attention is paid to the legal framework for the transmission of health information at the cross-border level. It is established that within the framework of European and Russian legislation at this stage, in the context of the formation of digital medicine, there is a comparability in the definition of legal mechanisms for the protection of medical data. It is also noted that in the issue of the transfer of personal health data to third countries, both the Russian Federation and the European Union choose the path of strict restrictive regulation and the introduction of a closed list of grounds for overcoming the ban on cross-border transfer. The reasons for this approach to issues of supranational interaction in healthcare are analyzed, as well as the potential risks of inertia of national legislators in this issue. Based on the analysis, the authors propose a number of amendments and additions to the national legislation on personal data, aimed at simplifying the interaction between jurisdictions on the transfer of confidential medical information. The authors suggest an international agreement on the exchange of medical data in digital format, which potentially should include not only the Russian Federation and the EU states, but also other countries, including Eurasian Economic Union member states, China, and countries of the American continent. The proposed concept is intended to create an opportunity for the formation of a supranational information system in the field of healthcare, which allows for the effective exchange of medical data, taking into account the sovereign interests of the countries participating in the agreement.