This article addresses the highly variable middle-class attitudes regarding political transitions and suggests that social mobility is a key factor conditioning its behavior. Social mobility creates a trade-off for the middle class between autocracy, which yields lower redistribution today, and democracy, which guarantees higher redistribution tomorrow. The way this trade-off is resolved impacts middle-class attitudes toward democratic transitions. Even when the middle class prefers lower redistribution levels under autocracy today, the middle class may prefer democracy today to guarantee higher levels of redistribution in the future, if it feels vulnerable about its future prospects.