This article examines the broader question of how illicit enemy tactics impact the implementation of fundamental law of armed conflict (LOAC)/international humanitarian law (IHL) targeting obligations. In addressing these challenging questions, focus is placed on distinction obligations, lawful target engagement, and the practical realities of conflict against hybrid enemies. This article begins by summarizing the distinction obligation, emphasizing both its “positive” and “passive” components. This passive element is often overlooked, yet it is tightly woven into the fabric of LOAC/IHL targeting law. Emphasis on the positive obligation without consideration of the passive obligation distorts the logic of the law itself. Consideration is also placed on the threat-identification challenge of hybrid warfare, how urban warfare exacerbates this challenge, and the enemy tactics designed to exploit the distinction obligation to gain a tactical and strategic advantage. The permissible and impermissible consequences of such enemy tactics are explored, and explanation is provided as to why it is impermissible and counter-productive to treat such tactics as a justification for ignoring the distinction obligation. This article proposes that these tactics form part of the totality of the circumstances related to lawful attack judgments, and therefore, must logically dilute the weight of the civilian presumption. The article concludes by explaining how failing to acknowledge this dilution imposes an unfair burden on lawful belligerents, grants the hybrid enemy an unjustified windfall, and distorts the assessment of overall operational legality.