Users share private information on the web through a variety of applications, such as email, instant messaging, social media, and document sharing. Unfortunately, recent revelations have shown that not only is users' data at risk from hackers and malicious insiders, but also from government surveillance. This state of affairs motivates the need for users to be able to encrypt their online data.In this dissertation, we explore how to help users encrypt their online data, with a special focus on securing email. First, we explore the design principles that are necessary to create usable, secure email. As part of this exploration, we conduct eight usability studies of eleven different secure email tools including a total of 347 participants. Second, we develop a novel, paired-participant methodology that allows us to test whether a given secure email system can be adopted in a grassroots fashion. Third, we apply our discovered design principles to PGP-based secure email, and demonstrate that these principles are sufficient to create the first PGP-based system that is usable by novices. We have also begun applying the lessons learned from our secure email research more generally to content-based encryption on the web. As part of this effort, we develop MessageGuard, a platform for accelerating research into usable, content-based encryption. Using MessageGuard, we build and evaluate Private Facebook Chat (PFC), a secure instant messaging system that integrates with Facebook Chat. Results from our usability analysis of PFC provided initial evidence that our design principles are also important components to usable, content-based encryption on the Web.



College and Department

Physical and Mathematical Sciences; Computer Science



Date Submitted


Document Type





Security, HCI, Usable security, Content-based encryption, Secure email, Webmail, End-to-end encryption, user study