In this chapter, digitalization in the field of tax administration is considered through the prism of the effectiveness of the use of digital technologies. The research focuses on the interaction of tax authorities with individuals through digital payment tools. The authors provide an overview of the technologies used by the Russian tax authorities and compare these technologies with international practices. Digital resources are divided by the authors into three levels: intended resources, direct interaction resources, and indirect interaction resources. Direct interaction resources are designed to inform taxpayers about their rights and obligations, as well as about the specifics of taxation at a specific time. Direct interaction tools allow tax authorities to actively interact with taxpayers using digital technologies. This helps to quickly resolve all issues, reduces possible errors and eliminates the possibility of unfair actions by tax authorities’ employees. Indirect interaction tools are aimed at involving individuals in the process of improving tax administration. The study is based on the analysis of statistical data from OECD reports, research papers and data from the Federal Tax Service of Russia. The aim of the study is to assess the level of development of digital technologies in the field of tax administration of the Russian Federation at three levels: information, direct interaction and indirect interaction. The research carried out in this paper allows us to state that digital technologies of tax administration in the Russian Federation are the most effective way to achieve this goal. The Russian Federation has reached a high level of development. The first- and second-level instruments correspond to the world's best performance standards. The results obtained show that taxpayers are well informed about the capabilities of these resources, highly appreciate their quality, and actively use them. At the same time, the data obtained indicate that digital resources of an indirect level of interaction, although they are technologically high-quality products, use an inefficient model of influence on the taxpayer. As a result, these tools are little used by taxpayers and do not bring those improvements in tax administration which they were created for. The conducted research makes it possible to assess the current state of digitalization in tax administration and identify possible improvements in this area.