The increasing prominence of new Internet and social media technologies and their growing importance as a source of health information are pushing the pharmaceutical industry towards digital channels. This paper explores the potential impacts of the pharmaceutical industry’s increasing interest in online marketing and considers how the existing regulatory framework in Canada translates into the social media sphere. Direct-to-consumer advertising (DTCA) of prescription drugs is prohibited in Canada, as it is in most industrialized countries. Although Health Canada has reaffirmed that the existing DTCA regulations apply to new Internet and social media technologies, new dynamics such as user-generated content, consumer propagation, and targeted marketing make applying the existing regulations an uncertain process. Moreover, certain problems often associated with DTCA may be exacerbated in the social media context. Finally, there is skepticism around whether government regulators have the resources or political will to effectively monitor new digital media. As such, this paper considers not only the role of direct government regulation in monitoring and enforcing the regulation of DTCA, but also the role of third party oversight and industry self-regulation—both of which may play an important role in filling the gaps in the regulation of the Internet and social media.