The situation in Syria has the potential to become a pivotal moment in the development of the law of armed conflict (LOAC). The ongoing brutality serves as a reminder of the importance of extending international humanitarian regulation into the realm of non-international armed hostilities; however, the very chaos those hostilities produce reveals critical fault lines in the current approach to determining the existence of an armed conflict. The international community’s year-long reluctance to characterize the situation in Syria as an armed conflict highlights a clear disparity between the object and purpose of the LOAC and the increasingly formalistic interpretation of the law’s triggering provisions. Focusing on Syria, this Article critiques the overly technical approach to the definition of non-international conflict currently in vogue—based on Prosecutor v. Tadić’s framework of intensity and organization—and how this approach undermines the original objectives of Common Article 3 of the Geneva Conventions. This overly legalistic focus on an elements test, rather than the totality of the circumstances, means that the world has witnessed a retrograde of international humanitarian efficacy: Syria appears to be a lawless conflict like those that inspired Common Article 3—the regime employs its full combat capability to shell entire cities, block humanitarian assistance, and target journalists and medical personnel directly. The LOAC is specifically designed to address exactly this type of conduct, and yet the discourse on Syria highlights the dangers of allowing over-legalization to override—and undermine—logic, resulting in a deleterious impact on human life.