School and district leaders are challenged to communicate with transparency and positivity with families and communities; however, over the past decade, social media has become an important avenue for communication. An appropriate use of social media can be a delicate endeavor, as errors in use or negative reactions can become a flashpoint. This is the case at Jester James Middle School (JJMS), where a teacher's seemingly innocuous comment in the hallway suddenly takes on a life of its own, given a negative parent response via social media that "goes viral." In this case, we explore the intersectionality of decision-making, communication, and social media use.