As the Internet has become more pervasive, so too have concerns about the security of personal data online. The rapid evolution of Internet technology has outpaced the legislative process, leaving courts to resolve complex and important questions of policy. Their answers to these questions can have dramatic implications for the future of the Internet as a platform for global communication. The judicial decisions in this area are frequently issued ad hoc by judges who may be unfamiliar with the technology at issue and unaware of the potential ramifications of their rulings. The February 2010 conviction in Italy of three Google executives for violations of data protection laws sparked widespread controversy and criticism on this basis. This Comment argues that the Italian court’s decision is a prominent example of the broader trend of inexpert judicial regulation of the Internet.