With the pervasiveness of the Internet in students’ lives, schools are frequently disrupted by their students’ online speech, whether through threats of violence, cyberbullying, or discussion of self-harm. To combat and minimize these disturbances, some schools are turning to third-party surveillance companies to monitor students’ Internet posts for potentially harmful speech. The U.S. Supreme Court has never addressed a school’s relationship to its students’ Internet postings. In the absence of Supreme Court guidance, lower courts rely primarily on a 1969 free speech ruling from Tinker v. Des Moines Independent Community School District, which asks whether a student’s speech substantially disrupts the educational process. If it does, a school may punish the student for that speech. This Note analyzes the effects that Internet surveillance could have on students and advocates that the Supreme Court grant certiorari to student Internet speech cases and adopt a risk of substantial disruption standard. Additionally, proactive schools should substitute Internet surveillance with an increase in tech-savvy counselors and social media education, each of which may positively guide students toward responsible Internet behavior.