Extended Hell(o): A Comprehensive Large-Scale Study on Email Confidentiality and Integrity Mechanisms in the Wild

The core specifications of electronic mail as used today date back as early as the 1970s. At that time, security did not play a significant role in developing communication protocols. These shortcomings still manifest themselves today in the prevalence of phishing and the reliance on opportunistic encryption. Besides STARTTLS, various mechanisms such as SPF, DKIM, DMARC, DANE, and MTA-STS have been proposed. However, related work has shown that not all providers support them and that misconfigurations are common. In this work, we provide a comprehensive overview of the current state of email confidentiality and integrity measures, as well as the effectiveness of their deployment. On a positive note, support for incoming TLS connections has significantly increased over the years, with over 96% of reachable MXs in the top 10 million domains allowing for explicit TLS. Notably, 30% of presented certificates are invalid, though, with the majority of issues related to the presented hostnames. In light of this, all 47 providers we tested connect to hosts with expired, self-signed, non-matching certificates, making it trivial for attackers to intercept their connections. Our analysis also shows that still only around 40% of sites specify SPF, and even high-ranked providers like t-online.de do not enforce it. Similarly, while DNS lookups are performed for both DKIM and DANE, neither mechanism is validated or enforced by all providers. In addition, we show that MTA-STS is only slowly getting traction (six providers support it) and provide the first large-scale analysis into OPENPGPKEY and SMIMEA records. All in all, this still paints a grim yet slightly improving picture for the state of email security by late 2022.