Middle powers in the Arabian Gulf and the Middle East have been gradually building strategic partnerships in the Horn of Africa region during the past decade, often through agricultural and mining deals, defence pacts and public infrastructure projects. Preferring personalised relations with the region’s power brokers, these transactional, interest-driven partnerships have crystallised into new networks for regional influence and power. The rivalry and competition among the Horn’s rulers over these new sources of money and power, leveraged to secure loyalty and fund violence for survival, have created a potent catalyst for regional instability. This geopolitical development has grown out of a wider multipolar world, where multiple middle powers have emerged to challenge the unfettered influence of a global hegemon (the U.S and the West), putting, as a result, the limits of a rules based, international order to test. In the wake of shifting geopolitical realities in the Horn, this article proposes hybrid and pragmatic approaches to peace diplomacy, that must anchor normative principles in the realities of power politics.