This chapter addresses current trends in student- and employee-related legal issues facing private schools, colleges, and universities. These legal issues generally reflect the more transactional nature of relationships with educational institutions and the more demanding expectations for services. Student concerns about the educational environment have focused on conduct, health, and safety, particularly with regard to sexual harassment and disability accommodations. Employee concerns about the workplace have been broader but also focused on misconduct, with upward trends in retaliation and discrimination claims, particularly disability discrimination. Strategies and best practices for successfully managing these legal challenges are also discussed.