Dissatisfaction is the trigger for states to initiate war according to power transition theory. The more a state is dissatisfied, the more likely it will initiate war. Traditionally, scholars use military buildups and alliance portfolios to measure states' dissatisfaction. Those measures do not express state dissatisfaction directly but provide, at best, circumstantial evidence. This paper introduces a direct measure of state dissatisfaction by counting requests and threats made by one state to another state. Four types of cases are selected from combinations of state dissatisfaction and initiation of war. The analyses are based on a selected-focus-dyad unit and quantified data sets. Using Boolean algebra, this article demonstrates that military parity and dissatisfaction expressed by territorial threats are more likely to trigger war. The results also show what elements of power parity and state dissatisfaction contribute to noninitiation of war. Last, the case studies highlight the nuances in the decision to initiate war among various states.