The outbreak of the Somali civil war in 1988, the toppling of Siad Barre’s dictatorial regime in 1991, and the subsequent disbanding of the Somali National Army (SNA) created a decade-long power vacuum in Somalia. In the wake of this collapse, many of the disparate anti-Barre opposition groups seized upon the vacuum in central authority to compete for influence. Within this vacuum of effective governance, the condition of lawlessness produced a sundry series of actors (variously termed as warlords, insurgents, and militants) who prospered on war, chaos, and criminality. A grassroots response to the disorder – the formation of the Union of Islamic Courts – brought a religious dimension and provided an opportunity for extremist religious organizers to insert themselves into local governance. Out of the more radical remains of the Islamic Courts, al-Shabaab arose and eventually evolved to formally become part of the alQaeda enterprise. The focus of this paper is to examine the nexus of Somali security sector development, Somali political development, and international efforts to foster effective governance despite the countervailing pressure of a domestic terrorist group with regional ambitions. It will identify the impending critical juncture in the process, and provide recommendations for the establishment of a durable central authority within the specific context of Somali culture which will be resilient enough to counter al-Shabaab and re-establish effective Somali governance outside Mogadishu.