During more than a decade of violent conflict (1980–1992) involving the military, rebel forces, and paramilitary “death squads,” El Salvador suffered some 75,000 casualties, mostly civilians. After three years of negotiations, the government and the largest rebel group signed a historic comprehensive peace accord that brought an end to the war and instituted wide-reaching political and social reforms. This agreement, and the peace process that produced it, has been widely hailed as a successful example of a negotiated end to civil war. In order to understand the conditions that led to the 1992 Chapultepec Peace Accords ending the war, this article tests ripeness theory in the context of the Salvadoran peace process. This article affirms the validity of theories of ripeness and the mutually hurting stalemate as structural explanations for the initiation of dialogue and notes the role of “indicators of ripeness” in forcing the parties to recognize a hurting stalemate that may already exist. It also proposes several hypothesized explanations for the effectiveness of the Salvadoran negotiations themselves. These explanations include the presence of strong, empowered policy entrepreneurs on both sides with the political will and capability to make credible commitments; the combination of internal and external pressure for a negotiated solution that raised the cost of defection; and the active involvement, based on consent of both parties, of a neutral, empowered, and credible mediator who provided both technical assistance and vigilance to move the process forward. After analyzing the Salvadoran case through this theoretical lens, the article applies the same concepts to contemporary conflict cases such as Iraq and Colombia, discussing how the lessons learned in El Salvador do and do not provide instructive guidance for managing civil conflicts today.