Influential recent scholarship assumes that authoritarian rulers act as perfect agents of economic elites, foreclosing the possibility that economic elites may at times prefer democracy absent a popular threat from below. Motivated by a puzzling set of democratic transitions, we relax this assumption and examine how elite uncertainty about dictatorship-a novel and generalizable causal mechanism impacting democratization-can induce elite support for democracy. We construct a noisy signaling model in which a potential autocrat attempts to convince economic elites that he will be a faithful partner should elites install him in power. The model generates clear predictions about how two major types of elite uncertainty-uncertainty in a potential autocratic successor's policies produced by variance in the pool of would-be dictator types, and uncertainty in the truthfulness of policy promises made by potential autocratic successors-impact the likelihood of elite-driven democratization. We demonstrate the model's plausibility in a series of cases of democratic transition.