Organizations are increasingly outsourcing critical judgment to AI suppliers, mirroring the historical trajectory of Private Military Contractors (PMCs) that led to structural dependency and accountability loss. This article identifies the “Supplier Entrenchment Spiral,” a three-phase psychological process—superhumanization, moral disengagement, and normalization—that embeds vendors into the fabric of organizational decision-making. Using the case of Epic’s sepsis detection model, the authors illustrate how AI overreliance can degrade expert judgment and obscure liability. To prevent irreversible entrenchment, the provided diagnostic checklist can be used to identify psychological red flags and reclaim internal oversight.