The Horn of Africa (HoA) is on the threshold of a long-term transformation as the result of a confluence of political, economic, and social changes, namely, generational political leadership turnover as a reflection of the rise of a younger population; a palpable shift in governance approach from a “security-first” model to a “development-centered” one; and the return of geopolitics across the Red Sea, following global and regional political realignments. To steer the transformation in a sustainable and peaceful direction, the HoA has to enlist the assistance of external actors both as a source of trade and investment and as guarantors of regional peace and stability. This region-wide transformation presents challenges and opportunities for the implementation of the Chinese-proposed Belt and Road Initiative (BRI). Beijing should better align the economic connectivity-focused BRI with the development-centered approach of regional states, build national and regional capacity for HoA security governance, and join local and external actors in a multilateral effort to ensure a peaceful, secure, and economically dynamic HoA.