This chapter provides context for the later chapters of the book. It presents some background, through case law, on the judicial view of school authority over students’ off-campus behavior. While schools have long exercised power to regulate students’ behaviors off-campus, such regulatory powers are not unbridled. The Free Speech Clause of the First Amendment to the United States Constitution guarantees the right of free speech to all Americans. This Amendment provides in pertinent part: “Congress shall make no law … abridging the freedom of speech.” While the language starts with the word “Congress”, the United States Supreme Court has interpreted the Amendment as applicable to the states and school districts via the Fourteenth Amendment (Gitlow v. New York, 1925; Engel v. Vitale, 1962). The question becomes whether the First Amendment protects students from school censorship of speech when they speak off-campus. The chapter discusses the origins of the idea of a schoolhouse gate – a phrase the United States Supreme Court introduced into First Amendment jurisprudence in 1969. The failure of the United States Supreme Court to define this phrase and to specifically address the constitutional right of students to free speech off-campus has created uncertainty in the lower courts – as evidenced in later chapters of this book. The chapter per the authors highlights the incertitude in the lower courts about the reach of schools’ censorship power when students are off-campus. As a consequence of this uncertainty, schools have taken great liberties with censoring students’ off-campus speech by imposing several forms of discipline for speech. The objective is to create an awareness of the need for judicial action to resolve the uncertainty in the student-speech jurisprudence so as to limit the incidents of school censorship of protected off-campus student speech.