The modern day school administrator understands that the First Amendment right to free speech is becoming more and more complex in the public school environment. Where students do have constitutional rights in the school atmosphere, the school administration does have protection when facing potential legal ramifications. A school official, be it a principal, superintendent, or school board, must take a proactive approach to address and possibly avoid situations that could possibly violate the constitutional rights of the students in the area of free expression. It is the responsibility of school officials to provide a safe and secure learning environment for students, free from substantial or material disruptions; lewd, offensive, or profane language; and messages containing references to drug use and drug paraphernalia. This research project is a qualitative study reviewing law cases citing Bethel School District v. Fraser (1986) and then analyzing the decisions made in each. The study included court cases that cited Bethel v. Fraser (1986) from 2000-2010 in order to allow for an adequate number of cases for analysis. The intent was to use the Shepard's United States Citations, which provided a useful tool for investigating the cases with the Bethel citation, while at the same time providing the researcher with a resource of relevant cases. The lineage of cases in this study has revealed 34 principles that could possibly decrease litigation for school officials in the area of the First Amendment right to free expression.