“Democratic conditionality” is the core strategy of the European Union to induce nonmember states to comply with its principles of legitimate statehood. This paper addresses two basic questions about democratic conditionality: How does it work, and under which conditions is it effective? In order to answer these questions, we offer a theoretical discussion of strategies and mechanisms of conditionality as well as their conditions of success. Then we analyze the EU strategy of conditionality and the conditions under which it is effective in the European non-member states. To explore the “conditions of conditionality”, we study four cases of sustained non-compliance with European human rights and democracy standards in a comparative research design: Belarus, Slovakia under Meciar, Turkey, and Latvia. The main strategy of conditionality used by the EU is “reinforcement by reward”. The EU reacts to the fulfillment or non-fulfillment of its conditions by granting or withholding rewards but does not engage in the coercion or support of non-compliant states. In addition, because of “weak” societies and “electoral volatility” in the countries we study, the central channel of effective reinforcement is intergovernmental. The main finding of this paper is that, even though the EU has used both material and social incentives to induce target governments to comply with its human rights and democracy standards, material bargaining, and above all the incentive of membership, have proved to be the most relevant mechanism of democratic conditionality. However, even the prospect of EU membership only produces compliance if the power costs of adaptation for the target governments are small. The “costs of Europe”, not “commitment to Europe”, is the central explanatory factor for compliance and effective democratic conditionality.