This paper investigates the intersection of student First Amendment free speech rights and off-campus electronic speech that targets school employees. Specifically, this study researched case law involving students who were disciplined as a result of off-campus electronic speech that targeted a staff member at their school. Analysis of case law and court decisions provides insight about how courts are interpreting and applying Tinker and other foundational student speech decisions in today's era of digital communication. The paper concludes with a set of recommendations for school administrators around the topic of student electronic speech that targets school employees. By implementing some of these practices in schools, school administrators will be better positioned to prevent this type of cyberspeech from occurring and to respond to it if and when the need arises.