An unprecedented increase in students’ personal technology use presents a new area for study within the educational leadership and administration field. Cellular phones, video-posting websites, and online social networking destinations empower students to create and distribute school-related images and stories. Student-developed media content can conflict with the image that school leaders and teachers strive to project through their public relations programs. The growing sense that any school or classroom event may suddenly appear on the Internet has exacerbated tensions among key human resources personnel, including teachers and administrators. To help initiate a conversation regarding these inchoate yet urgent issues of public relations and human resources, this study examined institutional reactions to the current media usage of students. It applied relevant perspectives from history, educational reform, and politics to enrich the analysis of emergent trends. The article concludes with a consideration of how school communities might best adapt to this challenging cultural issue.