In two of the case studies, Aceh and Sudan, the parties reached an agreement in the negotiation, while in the third case, Sri Lanka, the negotiations failed. Comparing the cases of success and failure through the lens of readiness theory and its amendments, this chapter analyzes various factors affecting the dynamics that induced readiness to negotiate in all three cases and readiness for agreement in the cases of Aceh and Sudan, as well as the factors that led to failure in the Sri Lanka negotiations. The concept of readiness theory seemed to allow flexibility and an understanding of the complexity of the elements that influence de-escalation processes in interstate or intrastate conflicts. Most of readiness theory’s variables and hypothesizes were validated in the pre-negotiation phase, helping to explain the factors underlying the parties’ agreement to start formal negotiations, and proved useful in the negotiation phase in explaining the parties’ readiness to sign an agreement in the negotiation phase.