Many of the principles of taxation that were developed in the first half of the 20th century, such as the arm’s length principle and the definition of the term “permanent establishment” (PE) in determining the tax position of international business operations, when applied to the business models of the 21st century, often result in the under-taxation of businesses that are otherwise fully compliant with the laws as presently written and implemented. Compounding the problem is the fact that these rules and principles of taxation are broadly recognized and are enshrined in a wide network of tax treaties. This makes the task of modifying or updating these rules and principals extremely difficult. Using legal-dogmatic and legal-theoretical methods, the author will show that present attempts to tax e-commerce transactions unilaterally are not effective and that, under present conditions, even organizations such as the EU are unable to address the problem at hand. The OECD project, commissioned by the G-20, which seeks to create a set of international e-commerce taxation rules, faces some very serious difficulties – largely because a well-established “set in stone” complement of internationally accepted laws, rules, and regulations is serving to block the development of new, more appropriate rules. This phenomenon has become known as the lock-in effect or legal impossibilism. In order to effectively address this phenomenon, lawmakers on a global basis must understand the mechanisms that are blocking the effective evolution of business taxation.