Teenagers straddle that fine line between childhood and adulthood, at times putting both feet on one side of the line, only to jump to the other side on another day. As parents, lawmakers, and scholars struggle to figure out just how much adult responsibility teens should be allowed, teens continue to push for new freedoms. All this maneuvering often results in conflict, especially in secondary schools, where the struggle is perhaps the most pronounced. One focus of the conflict occurring in schools has been whether the First Amendment covers students once they enter the educational setting. In order to teach students responsibility, schools must give students room to experiment with free speech rights. On the other hand, students must learn about more than their civil rights during school hour; thus administrators must have enough control over student speech to ensure it does not interfere with academic studies. The question courts face is where to draw the line. This Article argues that in Henerey v. City of St. Charles, the United States Court of Appeals for the Eighth Circuit drew the line in favor of school administrators. This decision effectively eliminated whatever experimental breathing room students previously had to responsibly explore their free speech rights.

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