This chapter presents and analyzes three cases of employee use of social media and corporate responses by using the rhetoric network theory: well-publicized case of Justine Sacco, a case drawn from the interview with the President and CEO of a US textile company and a case drawn from the interview with an HR executive of a US candy-making company. As Justine Sacco found out so brutally, communicative actors never act in isolation; as Henry Truslow IV discovered, company values and expectations need to be clearly articulated so as to influence communications throughout the network; and World's Finest Chocolate recognized the need to transform company culture and communications so as to adapt to the new communication technology (CTs) shaping professional communication. Because Sacco was a public relations executive charged with overseeing communications for IAC and their many clients, her digital communications, once retweeted beyond her immediate circle, were being viewed in a very public forum.