The Fourth Amendment protects citizens “against unreasonable searches and seizures” unless the search is founded “upon probable cause.” However, it has been almost a quarter of a century since the U.S. Supreme Court first established the reasonableness standard for searches conducted in schools in its decision, New Jersey v. T.L.O. Despite over twenty years of disparate analysis of the reasonableness standard in this nation’s courts since the T.L.O. standard was handed down, the Supreme Court has recently affirmed its confidence in the test in Safford Unified School District No. 1 v. Redding. Nevertheless, predictability and uniformity of adjudication on the subject of school searches have been compromised due to confusion on how to properly apply the reasonableness standard. This confusion is due in large part to the Supreme Court’s inability to firmly define, in exact terms, how much power a school can exercise over students. There are several reasons why the Supreme Court has not been able to concretely commit to both what constitutional rights students are entitled to enjoy in a school, and the depth of those rights. This Note will explore the two most salient reasons why the Court has failed to properly define students’ constitutional rights. First, the Court’s grant of constitutional rights to students has changed pursuant to the Court’s oscillation in its conception of how much power schools’ should wield over their students. And second, the doctrine of in loco parentis has historically underscored the Court’s legal analysis on how much control a school is entitled to exercise over its students.