Conflict of laws in cross-border healthcare relationships constitutes one of the most complex and challenging issues in Private International Law. In the contemporary era, the healthcare sector has undergone a profound transformation driven by globalization and rapid technological advancement. Medical relationships are no longer confined to the territorial boundaries of a single state; rather, they have evolved into transnational legal relationships involving parties subject to different legal systems. Such relationships arise through the cross-border movement of patients and healthcare services, where multiple connecting factors compete in determining the applicable law and legal liability, including the place where the medical service is provided, the law of the patient's domicile, the patient's nationality, and the place where the damage occurs. Moreover, the application of foreign law may be excluded where it is contrary to public policy. This conflict has become particularly significant in the digital age, as the identification of individuals and the determination of their national affiliation present considerable challenges due to the widespread use of remote healthcare services and modern communication technologies. These challenges are further intensified by the interaction of multiple connecting factors, such as the patient's residence, the location of the physician or healthcare institution, the place of performance of the medical act, and the place where the injury materializes. This research aims to examine the rules adopted in the doctrine of Private International Law for resolving conflicts of laws in healthcare relationships. It analyzes the traditional connecting factors, including nationality, domicile, party autonomy, and the place where the harmful act occurred, and evaluates their adequacy in addressing the realities of the digital environment, which has diminished the relevance of territorial boundaries and rendered the localization of medical activities increasingly virtual. The study also explores contemporary approaches that advocate more flexible standards, such as the law of the closest connection, the protection of the weaker party (the patient), and the principle of legal security concerning health data. Particular attention is given to the role of these standards in balancing patient protection with the need to ensure stability and predictability in international healthcare transactions. The research concludes that traditional conflict-of-laws rules are no longer sufficient, by themselves, to regulate digital and cross-border healthcare relationships. Accordingly, there is a need to develop specialized connecting factors tailored to transnational medical relationships, taking into account the technological nature of health data and the distinctive characteristics of medical obligations. Such developments are essential to achieving legal justice, enhancing legal certainty, and strengthening trust in international healthcare services.