‘Think globally, act locally.’ Considering the recent trend to open the ‘black box’ of external democracy promotion, this could be the new slogan for international actors engaged in promoting democracy in different parts of the world. Both practitioners and scholars alike have begun to consider different country contexts in which external democracy promotion can take place (cf. European Commission 2003b, 2006g; McFaul, Magen and Stoner-Weiss 2008; White House 2006). They are especially interested in knowing the chances of success of different strategies. A first step towards a comprehensive impact assessment is to investigate the link between domestic, country-specific conditions and international democracy promotion efforts. So, how do democracy promotion efforts of external actors relate to the varying political situations on the ground? In this chapter, we systematically compare democracy promotion efforts of the United States (US) and the European Union (EU) across countries in the Mediterranean and the post-Soviet space since the early 1990s. Beyond a comparison between the two ‘powers’ (cf. Kagan 2003), our analysis seeks to capture if and how their efforts vary according to the specific political settings of Morocco, Tunisia, Belarus and Ukraine.