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The Global War on Terror, beginning in 2001, started U.S. military operations in Iraq and Afghanistan, facilitating the expansion of Private Military Contractors (PMCs) through a combination of operational necessity, strategic policy decisions, and systemic oversight failures. Despite their growing role, PMCs operate in legal and oversight grey zones. Despite a growing body of work on PMC accountability, there remains little agreement on how U.S. military interventions created conditions for their proliferation. This paper examines how U.S. military operations in Iraq and Afghanistan facilitated the expansion of PMC influence, resulting in reduced oversight and accountability for both the U.S. government and PMCs. This study employs a qualitative content analysis of government documents, third-party critiques, and case studies to examine how U.S. military operations enabled PMC expansion. Quantitative data is used from the analysis of government reports, PMC missions, and the effectiveness of oversight mechanisms. Accountability levels vary across administrations but consistently fail to ensure transparency and ethical governance. U.S. military campaigns created operational and legal space for PMCs. Also, oversight mechanisms that have been put in place for these accountability issues have fallen short of the implementation of policy and taking corrective action towards PMC human rights violations committed in Iraq and Afghanistan. PMCs’ ambiguous status blurs civilian-military lines and undermines international norms. These findings have implications for the need for more national and international regulation. Normalizing privatized warfare could lead to the erosion of democratic oversight of military operations.