While some cases may focus on using social media to advance the interests of a business or brand, this case is best positioned as a springboard for exploring social media as it may coexist with or be embedded in organizational life. The case depicts a challenge for a young direct report, a relatively inexperienced manager, and the manager's supervisor when the direct report reveals a passionate political opinion on Facebook and unwittingly links it to sensitive company information. The case discussion can (1) surface diverse student views on the uses of social media as they relate to work life; (2) encourage analysis of and decision-making in the context of a tricky multilevel managerial situation involving social media use, company nondisclosure policies, and communicating guidelines; and (3) consider how issues raised in the discussion may inform students' own choices as users of social media and as managers of people who use these channels. Larger managerial, organizational, and corporate communication issues that are complicated by employee social media use may arise in this class discussion, including: managing professional boundaries between levels of employees in an organization; the porous boundaries that exist between internal and external communication; and gray areas among private, personal, professional, political, and public speech.