Helping Johnny Understand and Avoid Mistakes: A Comparison of Automatic and Manual Encryption in Email

Private Webmail 2.0 (Pwm 2.0) improves upon the current state of the art by increasing the usability and practical security of secure email for ordinary users. More users are able to send and receive encrypted emails without mistakenly revealing sensitive information. In this paper we describe user interface traits that positively affect the usability and security of Pwm 2.0: (1) an artificial delay to encryption that enhances user confidence in Pwm 2.0 while simultaneously instructing users on who can read their encrypted messages; (2) a modified composition interface that helps protect users from mistakenly sending sensitive information in the clear; (3) an annotated secure email composition interface that instructs users on how to correctly use secure email; and (4) inline, context-sensitive tutorials, which improved view rates for tutorials from less than 10% in earlier systems to over 90% for Pwm 2.0. In a user study involving 51 participants we validate these interface modifications, and also show that the use of manual encryption has no effect on usability or security.