In his seminal work on the political economy of dictatorship, Ronald Wintrobe posited the existence of a “dictator's dilemma,” in which repression leaves an autocrat less secure by reducing information about discontent. We explore the nature and resolution of this dilemma with a formalization that builds on recent work in the political economy of nondemocracy. When the regime is sufficiently repressive, and the dictator's popularity correspondingly unclear to opposition as well as autocrat, the ruler faces two unattractive options: He can mobilize the repressive apparatus, even though there may be no threat to his rule, or he can refrain from mobilizing, even though the danger may be real. Semicompetitive elections can ease the dilemma through the controlled revelation of discontent. Paradoxically, the manipulation of information through such non-repressive means can allow for more rather than less repression.