Modern dictatorships hold elections. Contrary to our stereotypical views of autocratic politics, dictators often introduce elections with limited manipulation wherein they refrain from employing blatant electoral fraud and pro-regime electoral institutions. Why do such electoral reforms happen in autocracies? Do these elections destabilize autocratic rule? The Dictator’s Dilemma at the Ballot Box explores how dictators design elections and what consequences those elections have on political order. It argues that strong autocrats who can effectively garner popular support through extensive economic distribution become less dependent on coercive electioneering strategies. When autocrats fail to design elections properly, elections backfire in the form of coups, protests, and the opposition’s stunning election victories. The book’s theoretical implications are tested on a battery of cross-national analyses with newly collected data on autocratic elections and in-depth comparative case studies of the two Central Asian republics—Kazakhstan and Kyrgyzstan. The book’s findings suggest that indicators of free and fair elections in dictatorships may not be enough to achieve full-fledged democratization.