The digital transformation of the obligation to calculate and pay taxes is a step-by-step process, and each of the periods of development of legal regulation on the payment of taxes corresponds to its own characteristics and trends. In the course of the study, three stages of the development of new provisions of tax legislation on the payment of taxes related to the digitalization of the economy were identified: automation (informatization), digitalization itself and robotization, involving the introduction of artificial intelligence technology. The author points out the peculiarities of the introduction of digital services of the Federal Tax Service of Russia in the process of calculating and paying taxes, and also emphasizes the strengthening of the trend of tax (fiscal) unitarianism in connection with the introduction of a single tax payment mechanism. In the context of the relationship between the blockchain and the transformation of the Federal Tax Service of Russia into a digital platform, an analysis of the development of the concept of “smart” taxation is provided. To characterize the stage of robotization of the fulfillment of the duty to pay tax, examples of the use of artificial intelligence in the field of taxation are given, and attention is also drawn to the value of introducing the principle of human-centered use of artificial intelligence in tax relations.