When do elections in authoritarian regimes lead to democracy? Building from the distinction between competitive and hegemonic authoritarian regimes, I argue that presence of relatively weaker incumbents renders competitive authoritarian elections more prone to democratization, but only when domestic and international actors choose to actively pressure the regime. The effects of two forms of pressure—opposition electoral coalitions and international conditionality—are theorized. Propositions are tested using a comprehensive dataset of elections in authoritarian regimes from 1990 to 2007. Results support two core claims: that the effect of electoral pressure is conditional on the type of authoritarianism and that this greater vulnerability to pressure is the reason why competitive authoritarian elections are more likely to lead to democracy. In contrast, several alternative explanations—that differences across regime type are explained by alternation in power, better electoral conduct, or ongoing processes of liberalization—are not supported by the evidence.