When do judges follow rules expected to produce unjust results, and when do they intentionally misapply such rules to avoid injustice? Judicial rule-breaking is commonly observed when national dignity and morality are at stake, such as abolitionist judges charged with applying federal fugitive slave laws, or when lives hang in the balance, such as applications of criminal sentencing rules. Much less is understood about judicial rule-breaking in quotidian civil litigation, in spite of the sizeable impact on litigants and potential litigants, as well as the frequency with which judges face such decisions. This Article is the first to theoretically assess and empirically analyze judicial rule-breaking in the commonplace setting of applying two rules regarding sexual harassment. We find that the likelihood of rule-breaking increases when judges perceive that pleas to legislatively or judicially correct the rule that produces unfair results would go unanswered.