Chapter 1 establishes the theoretical foundation for understanding why states engage in insincere coercion by making compellent demands they expect and/or intend to be rejected. It introduces a sequential militarized conflict model detailing the strategic interactions between a coercer and a target, incorporating options for accommodation, brute force, and coercion. While conventional explanations, such as asymmetric information, commitment problems, and cognitive biases, help to understand why coercion inadvertently fails, they cannot account for why a state would intentionally pursue a coercive strategy designed to fail. To resolve this puzzle, the chapter relaxes standard unitary actor and limited time horizon assumptions to develop a four-part typology of insincere coercion. States intentionally court coercion failure to: mobilize international and/or domestic support for subsequent brute force or containment policies; make an example of the target to deter others; restore long-term deterrence by imposing costs that alter the target’s future calculations; or move the goalposts by increasing demands once the initial conflict reveals a favorable balance of power. Ultimately, this theoretical framework reveals how coercion failure serves as a rational instrument for achieving broader foreign policy success.