Somalia’s experience of terrorism has metastasized across the Horn of Africa region, engulfing Kenya, Ethiopia, Djibouti, and Uganda, into the theatre of global terrorism in the Eastern Africa region. Yet, despite the almost two decades of international intervention to contain the Al Shabaab al Muhajideen assaults in Somalia, the group has demonstrated immense resilience. The chapter therefore interrogates the historical, ideological, and structural dynamics of terrorism in Somalia in the search for better calibration of prospects for peace and stability in the terror-prone country.