School system personnel are charged with numerous difficult, and sometimes conflicting, tasks. One of those tasks is to teach their students about their free speech rights while also maintaining order in the school building. Sometimes, when students choose to exercise those rights the results put administrators in a difficult situation of trying to maintain order while not trampling on a student’s Constitutional rights. Further complicating these issues is the fact that many of the governing court cases in student free speech were decided before the invention of the internet, and social media is a hotbed of speech issues. Students’ rights to free speech are primarily governed by the Morse Quartet--four Supreme Court cases that help to define what is, and is not, allowed speech by students. Courts use the outcomes in these cases to decide if the speech in the case at hand is permissible. Some notable problems to this routine are the fact that cases frequently involve technology that was not used in any of the four benchmark cases, and the Supreme Court has never ruled on a case involving punishing a student for speech made off-campus. The purpose of this research was to study recent cases involving student speech and to determine what trends could be determined. The researcher hoped to extract information that would be useful to teachers and administrators when making determinations about student speech. This study also gives recommendations on how school systems should craft guidelines to define acceptable speech. The data for this study was accumulated using the Westlaw® online research system. The study looked at 92 cases from across the United States during the span from 2009-2017. Cases were analyzed using the method invented by Statsky and Wernet (1995). Cases were then sorted by topic, and rationales were examined to find commonality between cases. This sorting allowed for qualitative analysis and discussion.