Social media is a rapidly evolving form of digital communication in the modern age. Brands continue to focus increasing resources on garnering consumer attention on social media platforms and are demanding measurable results from agencies or internal social media marketing teams. To both increase and demonstrate the value of a brand’s social media presence, many companies are engaging in behaviors that entail riskier legal strategies. Perhaps the most substantial legal land mine is “real-time content,” in which brands create and post content on vastly accelerated timelines with truncated legal approval processes in order to interact meaningfully with consumers. This Note will examine the dearth of guidance in the current legal landscape and provide pragmatic advice to brands wishing to win at the real-time content marketing game. When activating social media platforms, brands should take stock of their corporate approval structures and preemptively determine the level of risk that a particular brand prefers with respect to the legal ramifications of its social media content. This is especially true when engaging in real-time with celebrities. In order to assess and mitigate social media risks, this Note argues that legal counsel should develop social media content guidelines and conduct regular content calendar review sessions with the social media account team in order to identify and remedy social media risks.