Subject. The article deals with the scope of application of digital technologies to tax monitoring and administration. Digitalization plays an important part in activities performed by the Federal Tax Service and helps reduce the administrative workload on both taxpayers and tax authority. The use of digital communication channels saves our time, because it allows to submit tax returns and send letters online. Furthermore, it enhances the efficiency of inoffice audits and helps identify eventual tax violations. Objectives. We review a set of digital services and technologies used by the Federal Tax Service, their effectiveness, and present our findings on taxpayers' attitude to ongoing digital reforms. Methods. The validity and argumentation are based on official statistics of the Federal Tax Service concerning the dynamics of tax revenues and inspections, quantitative research through questionnaires and analysis of the findings. Results. We examine a range of digital services and technologies, including the Automated Control System – Value Added Tax, a new type of cash registers – Automated Information System Marking, Federal Government Information System – Unified State Register of Civil Registry Office, and personal accounts of taxpayers. Moreover, the article presents results of a survey among owners and top managers of companies, identifying their opinion on the coming taxation reforms. Conclusions and Relevance. Digitalization helped the Federal Tax Service significantly increase the efficiency of tax audits, while reducing the frequency of tax audits and the number of fly-by-night companies and the likelihood of using informal tax administration schemes. However, authorities should find a balance between the enhancement of the taxation system and their relationship with businesses.