Almost anyone with a smartphone can recall a time when an online advertisement followed them from webpage to webpage, or mobile browser to mobile application, or even jumped from a mobile device to a desktop web browser. While some people see it as a harmless—or even helpful—quirk of the online world, others find it creepy and intrusive. In the absence of significant government regulation of online advertising practices, particularly aggrieved individuals have sought relief in the courts by alleging violations of ill-fitting statutes drafted decades ago. This note explores just such a case, Yershov v. Gannett, in which the First Circuit Court of Appeals pounded the proverbial square peg (mobile internet technology) into a round hole (the Video Privacy Protection Act of 1988). To provide the proper context for the case and court opinion, this note also includes a primer on the players and practices of the mobile advertising technology ecosystem. As this case note concludes, the issues with which the First Circuit wrestles would be much better addressed by those with the time and resources to explore and consider the profound nuance of an industry that effects such a large—and growing—percentage of the population on a daily basis.

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