Southeast Asia seems locked endlessly in a boom-and-bust cycle of democratizing, then regressing, then democratizing again. This review of the history of democracy and autocracy in Southeast Asia underscores three themes. First, Southeast Asia reminds us that support for democracy is always contingent. The chapter shows how readily factors such as political polarization and the failure of democracy to deliver on its promises can produce receptive audiences, if not full-on partners, for aspiring autocrats. Second, the chapter explore the ways in which institutions can keep autocratic sympathizers in the wings or in the game, and how institutional reforms, particularly those that seek greater political openness and broader empowerment, can, under some circumstances, stoke political divisions and provide fodder for these reactionary forces. Importantly, the chapter suggests, formal liberalization may elevate antidemocratic impulses, in ways that should by now be anticipated (by scholars, democracy promoters, policymakers). Finally, it is noted how seldom pro-democracy forces, even when present and active, command center-stage – though when they do, their influence can be powerful.