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When do sanctions succeed in nuclear inhibition? Is there a generalizable framework to estimate sanction effectiveness against nuclear aspirants? Instead of relying on partial equilibrium analysis, we conceptualize sanctions as three sequential phases—imposition of economic pain, conversation to political pressure, and creation (or failure thereof) of zone of possible agreement (ZOPA). The effectiveness of each phase is subject to phase-specific contextual variables, an aggregation of which helps measure individual sanction's effectiveness, conduct cross-case comparison, and estimate one's replicability in other cases. To illustrate its analytical utility, we analyze the divergent sanction outcomes between Iran in 2012–2015 and North Korea in 2013–2017. Iran was economically more vulnerable and politically less resilient, and its bargaining position was closer to a ZOPA than North Korea was. Our analysis questions the utility of economic sanctions against North Korea and helps expand the discussion away from the policy obsession with the role of China. Theoretically, it rectifies an imbalance against qualitative and holistic approach in the sanction literature and contributes to discussions about nuclear inhibition strategies.