The efforts to regulate asymmetric warfare, a generic term used to describe military clashes between state and non-state armed actors, are an ongoing challenge. Asymmetric warfare aggravates the dangers threatening civilians in armed conflicts. It renders their homes and public areas part of the battlefield, and too often indigenous armed groups utilize their vulnerability as a strategic asset. By analyzing the principle of proportionality, a prominent law of war precept aimed at limiting harm to civilians caught in the line of fire, this chapter explores a few of the substantial methodological errors that arise when IHL is applied to asymmetric war environments. This chapter diagnoses three interpretive “traps” that threaten to prevent the proper application of proportionality and provides recommendations geared at avoiding, or at least mitigating each “trap” and its effects. This chapter concludes that the complexities of asymmetric warfare require a conceptual shift to a structured model of proportionality in IHL.