Sexual harassment-related complaints in the workplaces have increased multifold in the recent past. It is unclear whether this is because of more frequent harassment incidents because victims feel more emboldened to report, or only because more media reports happen on these complaints these days. Regardless, employers have improved both preventive and recovery mechanisms in order to minimize the incidents, or if they happen, support the victims in the best possible manner and also to protect themselves from adverse judicial scrutiny. While courts do not necessarily consider the job related and psychological consequences of harassment cases, organizations also need to worry about these – even as they build lawsuit-proof systems. In this paper, we discuss five historically important US Supreme Court lawsuits that would later have major consequences for how sexual harassment complaints are dealt within our contemporary workplaces. The five pioneering cases that would be discussed are Meritor v. Vinson; Faragher v. City of Boca Raton; Burlington Industries v. Ellerth; Gebser et al. v. Lago Vista Independent School District; and, Davis v. Monroe County Board of Education. The paper specifically elaborates on the implications of the court decisions upon these cases for subordinate-supervisor and student-teacher relationships in the US universities. Most harassment cases in the university contexts are not between employees but between employees/faculty and customers/students and this makes straightforward interpretation of court rulings difficult. The resultant ambiguity, along with the interest of universities to protect their reputations by suppressing incidents, make pursuing harassment investigations difficult. While these cases did not succeed in providing a saturated sample for generating a cohesive or comprehensive set of guidelines, they nevertheless guided future court judgements and also organizational policies with respect to managing sexual harassment. In the conclusion section of this paper, the author offers a glimpse into newer forms of sexual harassment, particularly those mediated by social media technologies, and offers ways for organizations to deal with them. Keywords: business ethics, discrimination, sexual harassment, lawsuits, Civil Rights Act of 1964, Universities, Supreme Court, United States.