The European Union and United States have both recently updated their approaches to the issue of how to prevent indirect tax loss in the e-commerce sector. In December 2017, the Council of the European Union adopted a Directive which will profoundly modify the EU VAT distance selling rules and rules applicable to imports of goods to non-taxable persons as from 2021. In June 2018, The US Supreme Court, in South Dakota v. Wayfair, Inc., overruled binding case precedent which had prevented states from collecting sales tax from out-of-state retailers lacking “physical presence” in the states on sales to in-state residents. While awaiting implementation of these new rules, in this article, the authors explore from a comparative perspective how two fundamentally different systems are trying to address the same problem.