Herein, we examine how the United States and the European Union use trade agreements to advance the free flow of information and to promote digital rights online. In the 1980s and 1990s, after US policymakers tried to include language governing the free flow of information in trade agreements, other nations feared a threat to their sovereignty and their ability to restrict cross-border data flows in the interest of privacy or national security.In the twenty-first century, again many states have not responded positively to US and EU efforts to facilitate the free flow of information. They worry that the US dominates both the Internet economy and Internet governance in ways that benefit its interests. After the Snowden allegations, many states adopted strategies that restricted rather than enhanced the free flow of information. Without deliberate intent, efforts to set information free through trade liberalization may be making the Internet less free.Finally, the two trade giants are not fully in agreement on Internet freedom, but neither has linked policies to promote the free flow of information with policies to advance digital rights. Moreover, they do not agree as to when restrictions on information are necessary and when they are protectionist.