A large literature has examined the role of elections in autocratic politics. This literature has been particularly interested in the extent to which elections stabilize or destabilize autocratic regimes. One important aspect left unexplored in the research thus far is how the timing of such elections and the broader electoral cycle influence patterns of regime stability. This paper fills part of that gap and studies the regularity of elections in dictatorships. It argues that dictators that stage less regular elections may offset the destabilizing short-term effect of elections identified by the extant research. Dictators can take take advantage of election timing to stymie challengers and hinder civil society collective action. Statistical analyses of all electoral autocratic regimes in the post--WWII period provides support for this proposition and suggests that regimes that hold less regular elections are more durable. This pattern holds in models which, partially, attempt to account for endogenity.