Tax administrations are currently experiencing transformations worldwide. This phenomenon has an impact on traditional tax rules. Increased technological capabilities open the door to review procedural and substantial regulation. The reinforcement of reporting and transparency requirements, and the connectivity between information systems in the public and private sector, will probably have a decisive influence on the evolution of tax law. Chatbots capture relevant data about the legal persons subject to different types of tax obligations. This information may be used to prepare more detailed administrative guidance, or even design future normative reforms. To efficiently protect justice and the rule of law in taxation, a human-centered centered approach can deliver benefits, while minimizing risks. However, the multi-faceted nature of humans must be considered in order to sustain true digital rights. Some general charters are being developed, and their contents should be embedded in technology. Computation and tax experts should pay attention to the work of different oversight institutions.