Experts from the North have long tried to teach countries in the South how to tax. For decades, they assumed the main challenges were domestic and there was a right answer to be found somewhere in the developed world that could be replicated everywhere else. Only more recently have they dedicated more attention to the international realm, yet their solutions remain tied to technical rules designed by a few specialists, as exemplified by the OECD Secretariat’s “Unified Approach” for the taxation of the digital economy. From a critical and historical socio-legal perspective, this Article argues that such technocratic approaches are set to fail less-developed nations for as long as we continue to overlook the background causes of weak taxation at both the national and international levels. These involve difficulties in applying complex rule sets, but also the very way in which global tax policy is developed, who influences the process, and the resulting distributive consequences.