This paper sets out a strategy calling for a radical overhaul of the manner in which both the EU and aspiring member states define and implement what the Copenhagen criteria refer to as the “Rule of Law” in pursuit of the elusive goal of sustainability. While pointing to the limits of the current “anatomical method” centered on legal and institutional checklists, the paper stresses the existence of a fundamental dilemma between, on the one hand, the need to be more ambitious in assessing and promoting the “Rule of Law” and, on the other hand, the imperative to exercise humility and restraint regarding the claims made by the EU on behalf of “Rule of Law” assessment and assistance.