This chapter argues that the European union's (EU’s) eastwards expansion in particular marked a watershed moment in the development of the EU’s enlargement policy, and that this had momentous consequences for gender equality policy in the new member states. It also argues that, perhaps as a consequence of overwhelming interest in the eastern enlargement round, the literature on gender and enlargement is overwhelmingly focused on the process whereby prospective member states ‘download’ EU policy templates into domestic settings. The chapter provides an overview of the development of EU membership conditionality, the ways in which eastern enlargement differed from previous rounds, and the ways in which gender equality was incorporated into membership conditionality towards central and eastern European countries (CEECs). It focuses on the evolution of the enlargement literature, focusing primarily on the CEEC enlargement. The chapter identifies directions for future research, focusing on existing research gaps.