This Essay pays tribute to Professor Joel Reidenberg’s rich academic career and, specifically, to his contributions to the study of privacy policies. In doing so, this Essay takes a close look at privacy policies and possible ways to effectively intermediate their content through various labeling schemes. While severely flawed, privacy policies are here to stay. Therefore, an in-depth analysis of ways to enhance their efficiency is merited. This Essay thus examines key strategies for privacy-related intermediation, obstacles, and problems arising in the process, as well as possible solutions. The analysis weaves together theoretical and empirical privacy law scholarship (much of it by Professor Reidenberg), “classic” work on the limits of disclosure policy, and general scholarship on certification.

Part I of this Essay provides a brief introduction to privacy policies and the challenges of their intermediation. Part II examines the additional steps that must be taken to ensure that privacy intermediation is effective and efficient in terms of the system’s design, especially through setting disclosure objectives and priorities. It also addresses the use of personalized disclosure and its possible shortcomings. Part III assumes that privacy intermediation is successful and confronts the potential problems that may lead to the trivialization of labels and rankings over time. These dynamics result from a possible flood of appeals for reevaluation and ensuing grade inflation. This part also briefly explains how such concerns may be mitigated through proper design, tailored disclosures, and tinkering with the liability regime of intermediaries. This Essay concludes with some parting thoughts about Reidenberg’s substantial contribution to “law and technology” scholarship and the ways others may develop it in years to come.