Let's Encrypt is a free, open, and automated HTTPS certificate authority (CA) created to advance HTTPS adoption to the entire Web. Since its launch in late 2015, Let's Encrypt has grown to become the world's largest HTTPS CA, accounting for more currently valid certificates than all other browser-trusted CAs combined. By January 2019, it had issued over 538~million certificates for 223~million domain names. We describe how we built Let's Encrypt, including the architecture of the CA software system (Boulder) and the structure of the organization that operates it (ISRG), and we discuss lessons learned from the experience. We also describe the design of ACME, the IETF-standard protocol we created to automate CA--server interactions and certificate issuance, and survey the diverse ecosystem of ACME clients, including Certbot, a software agent we created to automate HTTPS deployment. Finally, we measure Let's Encrypt's impact on the Web and the CA ecosystem. We hope that the success of Let's Encrypt can provide a model for further enhancements to the Web PKI and for future Internet security infrastructure.

The SMTP protocol is responsible for carrying some of users' most intimate communication, but like other Internet protocols, authentication and confidentiality were added only as an afterthought. In this work, we present the first report on global adoption rates of SMTP security extensions, including: STARTTLS, SPF, DKIM, and DMARC. We present data from two perspectives: SMTP server configurations for the Alexa Top Million domains, and over a year of SMTP connections to and from Gmail. We find that the top mail providers (e.g., Gmail, Yahoo, and Outlook) all proactively encrypt and authenticate messages. However, these best practices have yet to reach widespread adoption in a long tail of over 700,000 SMTP servers, of which only 35% successfully configure encryption, and 1.1% specify a DMARC authentication policy. This security patchwork---paired with SMTP policies that favor failing open to allow gradual deployment---exposes users to attackers who downgrade TLS connections in favor of cleartext and who falsify MX records to reroute messages. We present evidence of such attacks in the wild, highlighting seven countries where more than 20% of inbound Gmail messages arrive in cleartext due to network attackers.

The Heartbleed vulnerability took the Internet by surprise in April 2014. The vulnerability, one of the most consequential since the advent of the commercial Internet, allowed attackers to remotely read protected memory from an estimated 24--55% of popular HTTPS sites. In this work, we perform a comprehensive, measurement-based analysis of the vulnerability's impact, including (1) tracking the vulnerable population, (2) monitoring patching behavior over time, (3) assessing the impact on the HTTPS certificate ecosystem, and (4) exposing real attacks that attempted to exploit the bug. Furthermore, we conduct a large-scale vulnerability notification experiment involving 150,000 hosts and observe a nearly 50% increase in patching by notified hosts. Drawing upon these analyses, we discuss what went well and what went poorly, in an effort to understand how the technical community can respond more effectively to such events in the future.

We report the results of a large-scale measurement study of the HTTPS certificate ecosystem---the public-key infrastructure that underlies nearly all secure web communications. Using data collected by performing 110 Internet-wide scans over 14 months, we gain detailed and temporally fine-grained visibility into this otherwise opaque area of security-critical infrastructure. We investigate the trust relationships among root authorities, intermediate authorities, and the leaf certificates used by web servers, ultimately identifying and classifying more than 1,800 entities that are able to issue certificates vouching for the identity of any website. We uncover practices that may put the security of the ecosystem at risk, and we identify frequent configuration problems that lead to user-facing errors and potential vulnerabilities. We conclude with lessons and recommendations to ensure the long-term health and security of the certificate ecosystem.