The paper is devoted to the study of the transformation of legal regulation of labor in a digital society. In a comparative legal manner the paper attempts to indicate changes in labor and social security laws, which are also associated with digitalization processes. The influence of digital technologies on modern society is constantly growing: the economy, the sphere of communications between people, culture, life are changing under the influence of artificial intelligence technologies, the Internet of things, digital twins and many others. The digital economy is changing the content of labor relations from the inside through automation and an increasing degree of production robotization. Robotics and complex computer programs transfer some of the functions that employees previously performed, and the share of artificial intelligence systems in the production and service sector is growing rapidly. The algorithms underlying digitalization “penetrate” into legal regulation thus expanding its tools. On the one hand, employees and employers experience the influence of algorithmization through a change in the production environment; on the other hand, processes of law transformation begin in order to adapt legal regulation to the conditions of a digital society to maintain its effectiveness as a social regulator. Based on the results of the study, it is possible to draw conclusions on the objective need for the use of digital instruments by law, which should take into account the level of technology achieved, the existence of a tendency to law algorithmization, and the prerequisites for the further dissemination of algorithms in the field of labor and its legal regulation.