Traditional email encryption methods are difficult to set up, as they require senders to obtain a message recipient's public key before a secure communication can be sent. Easy Accessible Secure Email (EASEmail) addresses the key establishment and exchange issues of encrypted email by using a lightweight symmetric key server. Users can send a secure email without establishing or exchanging keys with the recipient in advance. With usability as its primary goal, EASEmail strives to bring usable secure email communication to the masses.

The current state of email security is lacking, and the need for end-to-end encryption of email is clear. Recent research has begun to make progress towards usable, secure email for the masses (i.e., novice users without IT support). In this paper, we evaluate the usability implications of three different key management approaches: PGP, IBE, and passwords. Our work is the first formal A/B evaluation of the usability of different key management schemes, and the largest formal evaluation of secure email ever performed. Our results reveal interesting inherent usability trade-offs for each approach to secure email. Furthermore, our research results in the first fully-implemented PGP-based secure email system that has been shown to be usable for novice users. We share qualitative feedback from participants that provides valuable insights into user attitudes regarding each key management approach and secure email generally. Finally, our work provides an important validation of methodology and design principles described in prior work.

京都大学 / 0048 / 新制・課程博士 / 博士(情報学) / 甲第21975号 / 情博第703号 / 新制||情||121(附属図書館) / 京都大学大学院情報学研究科通信情報システム専攻 / (主査)教授 佐藤 高史, 教授 小野寺 秀俊, 教授 岡部 寿男 / 学位規則第4条第1項該当 / Doctor of Informatics / Kyoto University / DFAM

Secure email systems that use end-to-end encryption are the best method we have for ensuring user privacy and security in email communication. However, the adoption of secure email remains low, with previous studies suggesting mainly that secure email is too complex or inconvenient to use. However, the perspectives of those who have, in fact, chosen to use an encrypted email system are largely overlooked. To understand these perspectives, we conducted a semi-structured interview study that aims to provide a comprehensive understanding of the mindsets underlying adoption and use of secure email services. Our participants come from a variety of countries and vary in the amount of time they have been using secure email, how often they use it, and whether they use it as their primary account. Our results uncover that a defining reason for adopting a secure email system is to avoid surveillance from big tech companies. However, regardless of the complexity and accuracy of a person's mental model, our participants rarely send and receive encrypted emails, thus not making full use of the privacy they could obtain. These findings indicate that secure email systems could potentially find greater adoption by appealing to their privacy advantages, but privacy gains will be limited until a critical mass are able to join these systems and easily send encrypted emails to each other.

None of the three largest webmail service providers (serving over 1 billion users) support end-to-end message encryption. Encrypted email has never seen mass adoption because it is prohibitive for non-experts to use. Private WebMail (Pwm) is our extension to popular webmail systems that lets users easily encrypt sensitive messages without having to first contact the recipient and share information. It is designed to spread quickly in a grassroots fashion so that a user receiving their first encrypted message can quickly and easily start using the system. This thesis describes the design and implementation of Pwm, then measures its usability through analysis and a user study.

Billions of web-based email and chat messages are sent over the Internet every day. However, very few service providers support end-to-end privacy protection. While providing security for these messages is technically feasible, usability remains a challenge in this field. Recent research attempts to hide security details like key management and encryption in order to make the system more usable. However usability studies demonstrated that hiding these details may confuse the user and contribute to mistakes (e.g., sending out an email in plaintext when the user thought it would be encrypted). In an effort to increase trust and eliminate mistakes, this thesis presents the design of a browser-based manual encryption mechanism that supports automatic key-management and manual encryption. It also describes the Message Protector (MP) prototype. An evaluations of MP is presented based on a user study conducted on the campus of BYU.

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.

Participants from recent secure email user studies have expressed a need to use secure email tools only a few times a year. At the same time, Internet users are expressing concerns over the permanence of personal information on the Internet. Support for short-lived keys has the potential to address both of these problems. However, the short-lived keys usability and security space is underdeveloped and unexplored. In this thesis, we present an exploration of the short-lived keys usability and security design space. We implement both a short-lived keys and a long-term keys secure email prototype. With these two prototypes, we conduct a within-subjects user study. Results from our study show that participants believe the short-lived keys prototype is more secure and more trusted. Participants also provide feedback on what they want in a system supporting short-lived keys. They also discuss how concerned they are about the permanence of their information on the Internet and on their devices.