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The border dispute between Djibouti and Eritrea provides a rare example of twenty-first-century interstate conflict. While not a major conflict in terms of lives lost, its location in the Horn of Africa lends an importance to the event beyond its details. Through the mediation of the Government of Qatar, the two states initiated negotiation, but it took two years from the skirmish that began the dispute until the Qatari mediation bore fruit. This case is presented through the perspective of Zartman’s ripeness theory to identify the conditions in which Qatar’s mediation became effective. While Djibouti desired international and regional mediation from the start, the Eritreans were not amenable to mediation, taking the opportunity to link the border dispute with Djibouti to wider issues of the Ethiopian-Eritrean conflict. This article identifies the growing international pressure, especially in the United Nations, and the counsel of the Qataris as providing Eritrea with the “mutually hurting stalemate” that resulted in their acquiescence to mediation. The role of Qatar is highlighted, as it was able to effect mediation where international, regional, and functional organizations’ efforts were unsuccessful. This provides an example of the importance of the mediator in bringing recalcitrant parties to an understanding that negotiation initiation may be in their best interests.