This study focuses on the Kenyan mediation of the Somali conflict and strategic intervention engagement between 2002 and 2012.It reveals that Kenya's diplomatic and stabilization efforts had their own dynamics and challenges. This is especially so with regard to the preferred policy option of exercising diplomacy that utilizes soft-power resources. This diplomacy had to contend with sensitive aspects of the process involving the complicated engagement with the Somali conflict-constituencies, and a complex mapping of various actors and interests. Contrary to the expected outcomes, interests and issues proliferated, and the original peace-making agenda was consistently slowed down and complicated. The study reveals that Kenya which was and still is an "interested mediator" ought to exercise some considerable influence over mediation environments pertaining to such fragile states.This is having in mind that Kenya is an emerging African driver. It also emerged from the study that different intermediary cooperative roles should be recognized in the current peace-making and stabilization dynamics reflecting an intricate balance of soft and hard power capabilities that Kenya possesses.