Proportionality requires weighing the concrete and direct military advantage. Should the proportionality of an attack be affected by broader considerations, such as the context of the conflict and its circumstances? More specifically, can cultural or strategic considerations—such as each party’s capabilities, military goals or aims, sensibilities, and vulnerabilities—be weighed as part of the military advantage anticipated from an attack? The argument raised in this chapter is that in principle, states should not be differentiated according to their strategic and cultural sensitivities. However, there are state-specific factors that should be considered in assessing the application of the principle of proportionality. Examples of such factors are the technological abilities, defensive systems, and relative power of the parties to the conflict.