Judicial holdings regarding sexual harassment actions have put judges who want to ensure what they view as a just outcome in the awkward position of having to choose between following precedent or “breaking the rules.” This article presents a theoretical assessment and empirical analysis of judicial rule-breaking with regard to two rules relating to sexual harassment. The first such rule, established in the Oncale decision, opened the door to the “equal-opportunity harasser” who treats everyone badly and thus escapes the prohibition on harassment “due to sex.” The other rule, set forth in the Ellerth and Faragher decisions, establishes a two-prong requirement for companies to demonstrate that they should not be held liable in the case of sexual harassment of an employee. The requirements for the so-called affirmative defense are, first, that the employer acted reasonably in relation to a complaint, and second that the employee acted unreasonably, usually indicated by a tardy complaint. Our analysis of 131 cases finds that the likelihood of rule-breaking increases when judges perceive that an employer that is otherwise meritorious (that is, responds effectively to the complaint) could be held liable (in the case of Ellerth and Faragher). On the other hand, courts have followed the rule when an unjust outcome has small repercussions (as in Oncale). Of interest in this context is how the courts will treat a new sexual harassment rule, as outlined in the Supreme Court’s Vance decision.