The recent cascade of academic literature on where private military and security companies (PMSCs) sit in the international legal framework has been sparked by contemporary controversies such as the killing of seventeen civilians by PMSC employees in Nisoor Square, Baghdad. Commentators in the field have generally focused on States’ obligations under international humanitarian law (IHL) and the need for industry regulation, epitomized in the Montreux Document of 2008. This essay seeks to examine the privatization of war from a theoretical and historical perspective, by looking at the moral and ethical concerns often voiced in the debate over PMSCs, and the extent to which these have been taken into account by the Monfreux regulatory framework. The legal framework envisaged by the Montreux Document with regards to PMSC involvement in situations of war is primarily based on IHL, given that IHL is lex specialis in the context of international and internal armed conflicts. This is potentially problematic as IHL is arguably an amoral regime that legitimizes violence. However, when faced with a new dilemma such as that of PMSCs, one should ask not only how to adapt the current legal regime to accommodate these changes, but also what the underlying goals and purposes of the law should be. Thus, traditional hard law obligations, such as those under IHL, may not provide satisfactory solutions to the issue of PMSCs.