In the sphere of education, social media has posed enormous challenges and unleashed its potential as a venue to communicate with stakeholders. This case is a fictionalized version of several real cases related to the school leaders’ struggle with utilizing social media to accomplish changes in schools. This case describes two high school administrators’ exploration in school’s use of social media. All people and schools’ names are pseudonyms. The narratives in this case are presented to deepen the understanding of the role of schools’ social media in creating social capital, and to raise the acute awareness of legal issues of schools’ social media.