School discipline is a critical area for research, as student interaction with school institutional authority is one of the primary mechanisms whereby young people come into contact with and internalize societal norms, values, and rules. It is thus significant that the number of cases reaching state and federal appellate courts has surged back up to levels attained during the early 1970s when civil rights cases had a central place on the national political agenda. While Supreme Court decisions are important because every school in the nation must adhere in principle to its rulings, few landmark cases do not encompass the universe of legal challenges regarding school discipline and related policies. To discern the larger contours of the legal climate facing schools, the authors analyze all appellate-level federal and state court cases in which school efforts to discipline and control students have been challenged. As a whole, decisions in these cases are often complex and contradictory in providing practical guidance to schools regarding specific disciplinary matters. Over time, the authors found that courts in general have become less favorable to student claims on discipline-related cases. However, since the number of court challenges has increased in recent decades, the likelihood of a school facing a legal environment in which a student has recently been successful in a court challenge over school discipline has not significantly diminished. The authors' research indicates that both educators and students understand the former's authority to be more limited and the latter's rights more expansive than has actually been established by case law. In this article, the authors discuss how the emphasis on student rights continues in classrooms even when the Court begins to think otherwise. The authors stress that, as various social and political actors consider legal regulatory reforms, it is important to recognize that the expansion of students' legal entitlements has also increased the potential for student dissent in U.S. schools, whether of a political, religious, or ideological character. (Contains 2 figures and 1 table.