As society becomes increasingly dependent on technology, school leaders must navigate the evolution of websites, resources, and platforms, including social media, as part of their responsibility to facilitate a safe and productive learning environment for students. This article reviews both constitutional and case law as a means of informing educational leaders of their rights and duties, as well as providing a foundation upon which effective K-12 social media policies and practices for educators can be built. Specifically, we offer an analysis of landmark cases involving the First Amendment and free speech, the delicacy around teachers' roles as both public employees and private citizens, and recent court cases involving social media use. Additionally, we propose guidelines around social media use, compiled from both practitioners in the field and relevant literature.