During a 30-day window between late May and late June of 2020, President Donald Trump earned international attention not only for the content he posted to social media sites such as Twitter, but also for the ways in which social media companies responded to his posts. For the first time in history, social media posts from a sitting president were receiving warning labels, and in some instances were even deleted for violating Twitter's content guidelines, "The Twitter Rules." The substance of a debate over online content that began 25 years earlier had come full circle as a host of social media platforms—initially imagined to help people share group text messages and photos with friends—were now being referred to as the 21st century equivalent of a public square. Had Twitter's executive team gone too far by placing a warning notice on the president’s tweets? Would social media companies be able to adapt if the Trump administration's recommendations led to meaningful changes in the law that made "The Twitter Rules" actionable? How will companies prepare for an environment within which content policy is not simply a legal concern but a strategic decision?