Turkey’s Europeanization process has lost its dynamism since late 2005 at least partly because of the EU’s ambiguous attitude toward Turkish membership, which damaged the EU’s credibility and therefore the legitimacy underpinning its policy of democracy promotion. This article critically examines the evolution of Turkey’s accession to the EU, and the latter’s performance in democracy promotion. After a brief review of EU formal reports and declarations, the article analyzes the main shortcomings in Turkey’s democratization-cum-Europeanization process. It argues that the evolving nature of EU expectations, its perceived double standards, and growing opposition of some Western European countries to Turkey’s accession contributed to the weakening of EU’s democracy promotion in Turkey.