The subject of this study is the legal norms that establish the list of subjects to undergo compulsory medical examination, factors to be assessed during medical examination, as well as the procedure of medical examinations. The article is dedicated to the major aspects of the legal regulation of the procedure for medical examinations of workers engaged in the transportation.The purpose of the study is to identify trends in the legal regulation of medical examinations of workers engaged in the transportation, including those caused by the introduction of digitalization in these processes.Methodology. The empirical study consists of several stages. At the first stage, there was a sampling of types of transportation: road, railroad, water transportation and mass rapid transit. In the framework of the second stage the legislation regulating medical examinations of workers employed in these types of transport was analyzed using systemic, formal-legal and comparative-legal methods.The results of the study show that to date the legal regulation of the procedure of medical examinations using telemedicine technologies is being formed in some types of transportation. At the same time, the methods of medical examinations, indicators and psycho-traumatic factors have not been adjusted to the examination with digital technologies.Conclusions. There is a need for a differentiated approach to the legal regulation of medical examination of workers engaged in the transportation, depending on the type of transport. The authors draw attention to the outdated legal regulation of certain issues. For example, the list of professions of the ship staff of marine and inland water transport, the instruction on compulsory and periodic medical examinations was approved in 1989, and was canceled over 10 years ago.In connection with the growing interest in the development of high-speed railroad transportation, we believe that the regulations governing medical examinations of workers engaged in the transportation should be revised due to the need to include special norms establishing special studies or additional procedures required for admission to work in high-speed transportation.In addition, the authors suggest that employers should be granted the right to send their employees engaged in the transportation, whose employment contract has been suspended on the basis of the military service selection under mobilization of the Armed Forces of the Russian Federation, to take special medical examinations.