Nowhere else on the African Continent has the principle of self-determination been invoked in all its diverse manifestations as in the Horn of Africa. And nowhere else has so much ink been spilt to take positions in defence of or opposition to the invocation of self-determination in one form or another. Even more blood has been spilt due to the passionate quest for self-determination and the equally passionate determination to obstruct its realisation. And blood continues to flow as struggles for and against self-determination persist in large parts of the Horn of Africa into the new millennium. The actual wars being conducted in search of and opposition to the principle and their proxy verbal counterparts, however, do not seem to take into account the challenges, hazards, and opportunities that have come to the fore in the post-Cold War era. Contributing to the much needed effort of pushing the ongoing intellectual debate forward to situate it within the contemporary context is the primary aim of this chapter.