In canonical accounts of war, conflict outcomes are inherently uncertain. Contesting literatures posit that this uncertainty, arising from stochastic elements of the war-fighting process, may induce conflict due to greater risks of miscalculation or foster peace by breeding caution. We theorize that states, on average, exhibit prudence when confronting greater uncertainty. Despite its conceptual importance, extant proxies for uncertainty at various levels of analysis—such as polarity, balance of power, system concentration, and dyadic relative capabilities—are imprecise and theoretically inappropriate indicators. To overcome this shortcoming, we theorize the conditions that elevate the magnitude of uncertainty over conflict outcomes and introduce a novel measure that captures this uncertainty within any k-state system. Through extensive empirical analysis, we confirm uncertainty’s pacifying effect and show how this effect operates at different levels of analysis.