It is widely recognized that Slobadan Milošević’s electoral defeat in the Yugoslav presidential elections and his attempts to manipulate the results contributed to his downfall in October 2000. But it needs to be theorized why stolen elections are so important. They are “triggers” that create expectations of opposition success and cause outrage when voters are robbed of victory. They document widespread popular dissatisfaction while testing the loyalty of the regime’s staff. Electoral authoritarian regimes, such as Milošević’s, hold elections competitive enough to strengthen their domestic and international standing by allowing the opposition some room for maneuver without resorting to overt repression. Stolen elections reveal the structural ambiguity of this form of rule. The competitive nature of the elections enables the opposition to win while the manipulation of the results reveals the regime to be a desperate dictatorship. Theorizing the Serbian October shows why stolen elections make electoral authoritarianism so vulnerable to democratic revolution.