The blockchain technology has been projected to substantially disrupt numerous aspects of tax processes. This prediction has by and large not come to fruition yet. While every disruptive technology must overcome some barriers before realizing its full potential, the authors inquire whether there is something inherently hindering in the way current laws are drafted and constitutional guarantees formulated that prevents the blockchain from flourishing. The authors argue that, to reap the full benefits of automation via blockchain, the existing social institutions (legal framework) and the creative achievement (new technologies) must meet half way. On the one hand, new technologies such as blockchain must be established within the framework of the existing social structure and be fully subjected to the fundamental rights guaranteed by the legal order. On the other hand, the legal order itself must be transformed in a way that permits binary automated outcomes while preserving equity. This paper looks at the ways of achieving that.