Kenya and Somalia relations remain fragile due to short-term, quid pro quo approaches that fail to address long-term strategic interests. Tentative moves to ease tensions between Nairobi and Mogadishu are driven primarily by immediate political calculations rather than sustainable policy frameworks. Kenya, facing setbacks in the maritime dispute at The Hague, is keen to protect its investments in the Lamu Basin and has pulled out of the case, anticipating an inevitable ruling in Somalia’s favor. This has prompted Nairobi to seek concessions from Somalia, including the handover of warlord Abdirashid Janan to President Farmaajo, as part of broader efforts to recalibrate bilateral ties. However, Farmaajo’s refusal to leave Villa Somalia and his potential pursuit of a parliamentary mandate extension complicate Kenya’s strategy. The Somali president is reportedly pushing Kenya to abandon long-standing allies in Jubaland and to recognize his continued authority, heightening risks in an already transactional relationship. These developments underscore the limitations of short-term political bargaining and the dangers of relying on temporary deals to manage complex regional disputes. Analysts warn that without a clear, strategic approach, Kenya’s attempts at appeasing Mogadishu could backfire, undermining regional stability, long-term investments, and its influence in Horn of Africa politics.