Certificate Transparency (CT) is an emerging system for enabling the rapid discovery of malicious or misissued certificates. Initially standardized in 2013, CT is now finally beginning to see widespread support. Although CT provides desirable security benefits, web browsers cannot begin requiring all websites to support CT at once, due to the risk of breaking large numbers of websites. We discuss challenges for deployment, analyze the adoption of CT on the web, and measure the error rates experienced by users of the Google Chrome web browser. We find that CT has so far been widely adopted with minimal breakage and warnings. Security researchers often struggle with the tradeoff between security and user frustration: rolling out new security requirements often causes breakage. We view CT as a case study for deploying ecosystem-wide change while trying to minimize end user impact. We discuss the design properties of CT that made its success possible, as well as draw lessons from its risks and pitfalls that could be avoided in future large-scale security deployments.

HTTPS error warnings are supposed to alert browser users to network attacks. Unfortunately, a wide range of non-attack circumstances trigger hundreds of millions of spurious browser warnings per month. Spurious warnings frustrate users, hinder the widespread adoption of HTTPS, and undermine trust in browser warnings. We investigate the root causes of HTTPS error warnings in the field, with the goal of resolving benign errors.

We consider the effect attackers who disrupt anonymous communications have on the security of traditional high- and low-latency anonymous communication systems, as well as on the Hydra-Onion and Cashmere systems that aim to offer reliable mixing, and Salsa, a peer-to-peer anonymous communication network. We show that denial of service (DoS) lowers anonymity as messages need to get retransmitted to be delivered, presenting more opportunities for attack. We uncover a fundamental limit on the security of mix networks, showing that they cannot tolerate a majority of nodes being malicious. Cashmere, Hydra-Onion, and Salsa security is also badly affected by DoS attackers. Our results are backed by probabilistic modeling and extensive simulations and are of direct applicability to deployed anonymity systems.