Abstract: This article presents a historical overview of the emergence of tax monitoring in the Russian Federation, as well as the analysis of its peculiarities within the context of trends of global taxation practice. Modern nations apply new approaches to tax administration, but commonly emerging and practically established ideas do not receive due scientific research. The object of this research is the process of digitalization of tax administration based on Russian and foreign experience. The subject of this research is the theoretical aspects of tax monitoring, as well as historical analysis of the emergence of a new format of interaction between tax administration and taxpayers in Russia and global practice. The goal of this work is to determine the role and importance of tax monitoring within taxation system of the Russian Federation, as well definition of tax monitoring as the means of digitalization of tax administration. The scientific novelty of this work consists in the comprehensive research of implementation of tax monitoring from the moment of its emergence in the global practice of taxation and determination of its essential features, which allowed concluding on incorrectness of legislator’s definition of tax monitoring as a form of tax control, and call for legislative definition of the concept of “tax administration”, as well as amending the Taxation Code of the Russian Federation for clarification of the status of taxpayers, who transitioned to the digital model of tax administration. The results of this research can be used in development of amendments to the legislation and criteria for assessing efficiency of tax monitoring.