This special issue examines Western efforts at democracy promotion, reactions by illiberal challengers and regional powers, and political and societal conditions in target states. We argue that Western powers are not unequivocally committed to the promotion of democracy and human rights, while non-democratic regional powers cannot simply be described as “autocracy supporters”. This article introduces the special issue. First, illiberal regional powers are likely to respond to Western efforts at democracy promotion in third countries if they perceive challenges to their geostrategic interests in the region or to the survival of their regime. Second, Western democracy promoters react to countervailing policies by illiberal regimes if they prioritize democracy and human rights goals over stability and security goals which depends in turn on their perception of the situation in the target countries and their overall relationships to the non-democratic regional powers. Third, the effects on the ground mostly depend on the domestic configuration of forces. Western democracy promoters are likely to empower liberal groups in the target countries, while countervailing efforts by non-democratic regional powers will empower illiberal groups. In some cases, though, countervailing efforts by illiberal regimes have the counterintuitive effect of fostering democracy by strengthening democratic elites and civil society.