The recrudescence of conflict,war,and peace have been the main themes that illustrate the relationship between Eritrea and Ethiopia,the two important states in the Horn Africa.Eritrean cordial relations with Ethiopia in the aftermath period of its independence deemed as positive momentum for a potential new era of sustainable peace.Unfortunately,the expectation and the prospect of peaceful coexistence was shattered by the sudden eruption of border war over Badme on May 12,1998.After two years of bloody war,the conflict ended with the comprehensive Algiers peace agreement.However,Ethiopia’s request for further dialogue and Eritrea’s persistence on the implementation of the agreement left both countries in stalemate for eighteen years.In the midst of such a scenario on 5 June,2018 Ethiopia declared its willingness to accept the ruling of the court without any precondition.Subsequently,the two countries ended up signing the historic agreementa joint declaration for peace and friendship in the space of 35 days.Although the diplomatic thaw reversed the course history in favor of peace there are still unsettled issues reemerged again,and the core issue of the border dispute relating the physical demarcation hasn’t shown any significant development still this date.Given these circumstances,the relations of the two countries stand at crossroads.Therefore this study aims,firstly to understand what factors enabled the new rapprochement successful while the same framework failed to deliver peace for eighteen years.Secondly,it attempts to enumerate the fundamental factors that stalled the inclusive peace between the two countries.Thirdly the paper also tries to underpin an alternative peacebuilding framework for sustainable peace.These cases are presented through the theoretical and analytical lenses of ripeness theory,readiness theory,and the pyramid peacebuilding model.The study concludes that Ethiopia’s call for peace expedited by a combination of its domestic and foreign policies.The ripeness and readiness theories have more explanatory value to explain Eritrea’s and Ethiopia’s bold move towards the unexpected Peace.The study also argues that Ethiopia’s internal political instability coupled with the lack of institutionalizing approach posed a potential threat to the sustainability of peace in both countries.In the end,the study recommends John Paul Lederach’s pyramid model as a viable strategy to reconcile the two people who shared history,culture,language,and border.