This note discusses how the international community must respond to the complexity of modern Piracy with a framework that enumerates regulations for Privately Contracted Armed Security Personnel in concert with deterrence, regional support, and prosecution efforts. The dramatic increase in incidents of Piracy at sea off the coast of Somalia exacerbates the danger and expense faced by those in the commercial shipping industry and negatively impacts the efficiency of global trade. Escalation in Piracy has thus necessitated deployment of both naval vessels and privately contracted armed guards operating under an obscure legal framework that is largely undefined. The failure to provide a sustainable or efficient solution under the prevailing approach to counter-piracy requires that new strategic alternatives be further developed through greater understanding of counter-piracy operations by drawing upon its historical and contemporary necessity and the lessons learned from its operation in addition to the strengths and weaknesses of legislative responses within the international community. In this note, I first provide an introduction to the modern piracy epidemic so as to provide a contextual background for the reader and highlight the necessity of a multi-dimensional solution. Second, I present an overview of the legal framework under which privately contracted armed security companies operate, including recent initiatives undertaken to promote their regulation and accountability. Third, I demonstrate a trend towards ultimate acceptance and promotion of these actors among key industry players and states. Finally, I advance that the restructuring and re-framing of issues affords an extension of conceivable solutions, which permit integration of local knowledge and lessons learned in advancement of local support and prosecution efforts to achieve a sustainable and effective solution.