Scholars often study revolution and democratization in single countries, only haltingly observing the influence of international or regional factors, exogenous shocks, or transnational identities and interactions. Episodes of revolutionary contagion such as the collapse of communist regimes across Eastern Europe in 1989 and the uprisings against authoritarian regimes across much of the Arab World in 2011 demand closer attention to regional context and transnational dynamics, however, as revolutionary protest movements are rapidly emulated across neighboring countries. Individual country cases during such episodes of contagion do not stand alone, as the emergence and dynamics of each movement is influenced by its neighbors. This paper examines the relationships between cases in instances of regional revolutionary contagion, looking, first, at the systematic differences that can be expected between outcomes – related particularly with the relative timing with which uprisings occur – and, second, at common factors which nonetheless bind the uprisings in a given region together, exerting a similar though not determinative influence on outcomes. Comparing patterns of revolution and transition in 1989 and 2011, the author argues that there are often important and systematic differences between the states in which early and late uprisings occur during periods of regional revolutionary contagion. The societies that are the first to revolt (e.g. Poland, Tunisia) generally are able to achieve their goals with the least violence and transform their countries through the most constitutional and orderly processes. The countries in which revolutions are ignited later by the sparks from neighboring uprisings (e.g. Romania, Syria) are often the ones in which opposition is the least organized, the state is the most oppressive, and the revolution itself, as a result, unfolds with the most violence and chaos. In such settings, reforms can prove more difficult and democratic consolidation less orderly. While the paper’s findings concerning intra-regional variation could suggest a gloomy forecast for some of the Arab Awakening states, the author points to the ultimate relative success of the 1989 revolutions – even the more difficult ones – and concludes by suggesting factors unique to episodes of regional contagion that can influence all states in the revolutionary regions, tying transitional outcomes more closely together than analyses of country-level factors might lead one to expect. Shared identity, mutual oversight (and competition), and strong leadership by regional organizations can all play important and helpful roles in guiding post-revolutionary transitions.