Abstract: This article attempts to elucidate the nature of automation of labor in the context of works of the Russian revolutionist and founder of the Central Institute of Labor Alexey Gastev. The author depicts his legacy as an important conceptual resource with regards to comprehension of the constructive nature of automation, obscured in the context of the existent cultural background. Within the framework of this problem, the author articulates the human-machine system, as well as explicates the idea of “training” of psychophysiological qualities and the concept of socio-technical time within A. Gastev’s theory of scientific organization of labor. The research methodology contains the concept of “reappropriation” introduced by the contemporary theoretician Yuk Hui for designation of the ability to develop alternate forms of interaction with the technical objects; as well as the results of philosophical inquiries dedicated to the phenomenon of automation of labor, presented by such theoreticians as Paolo Virno, Bernard Stiegler and Benjamin Noys. The author determines that A. Gastev understands the work of human-machine system upon the conditions of training, presented as specific practices of materialization and modification of psychophysiology, as well fundamental shift in the nature of work of a technical object. This leads to the conclusion that automation does not represent an elemental process on substituting labor functions of a human, because its nature carries more constructive and holistic character. In other words, the nature of automation can be understood as a range of variable means of reappropriation or organization of the human-machine system.