In this chapter we investigate the causes of dictatorial survival and breakdown, as well as why breakdown sometimes leads to democratization. Military-led regimes last less long than civilian, but personalization increases their durability while it reduces longevity in party-led regimes. Leadership changes can lead to regime collapse. The death of a dictator who has concentrated great power in his hands is especially likely to cause regime crisis. Personalization also affects the likelihood of a peaceful, negotiated transition, once survival appears unlikely. Dictatorships with more collegial decision making tend to negotiate their extrication from power, but personalized dictatorships often fight to the bitter end. Junta-led dictatorships usually negotiate peaceful transitions to democracy. Collegial civilian-led dictatorships less often exit peacefully than junta-led regimes, but more often than personalized regimes, whether civilian or military. Where a transition occurs peacefully via negotiation, the immediate outcome is usually democracy. Where, however, the dictator hangs on until forceful overthrow, democracy is less likely.