The main question driving the inquiry undertaken in this chapter is why, despite all of the efforts exerted regionally and internationally as solutions to the piracy dilemma, Somali piracy has not only existed but flourished and escalated. In answering this question, I turn to the theoretical framework for contagion, embedded risk factors, and the gaps in literature and policy. Neither scholars nor policy has paid enough attention to the complexities and mutually reinforcing risk factors driving piracy in Somalia. A significant body of literature has been devoted to assessing the liberal peace interventions by the international community. However, scholars continue to miss the mark in several ways: (1) inadequate conflict analysis of the dynamic interplay of pirates- and on-land challenges, (2) narrow and too generalized theories of change through Western-led military interventions, (3) the voices and presence on pirates in decision making (4) sea interventions that have exacerbated the increase of pirates. The liberal peace theoretical framework that provides framing of pirates has conceptualized pirates as “anarchy” and a “threat multiplier” to the international shipping system on the Indian Ocean. However, research findings reveal a broadened conception of pirates by local people as providers of four intricately related levels of security: economic security, societal security, environmental security, and military security.