Open Access

OpenPGP is one of the two major standards for end-to-end email security. Several studies showed that serious usability issues exist with tools implementing this standard. However, a widespread assumption is that expert users can handle these tools and detect signature spoofing attacks. We present a user study investigating expert users' strategies to detect signature spoofing attacks in Thunderbird. We observed 25 expert users while they classified eight emails as either having a legitimate signature or not. Studying expert users explicitly gives us an upper bound of attack detection rates of all users dealing with PGP signatures. 52% of participants fell for at least one out of four signature spoofing attacks. Overall, participants did not have an established strategy for evaluating email signature legitimacy. We observed our participants apply 23 different types of checks when inspecting signed emails, but only 8 of these checks tended to be useful in identifying the spoofed or invalid signatures. In performing their checks, participants were frequently startled, confused, or annoyed with the user interface, which they found supported them little. All these results paint a clear picture: Even expert users struggle to verify email signatures, usability issues in email security are not limited to novice users, and developers may need proper guidance on implementing email signature GUIs correctly.

TLS is one of today's most widely used and best-analyzed encryption technologies. However, for historical reasons, TLS for email protocols is often not used directly but negotiated via STARTTLS. This additional negotiation adds complexity and was prone to security vulnerabilities such as naive STARTTLS stripping or command injection attacks in the past. We perform the first structured analysis of STARTTLS in SMTP, POP3, and IMAP and introduce EAST, a semi-automatic testing toolkit with more than 100 test cases covering a wide range of variants of STARTTLS stripping, command and response injections, tampering attacks, and UI spoofing attacks for email protocols. Our analysis focuses on the confidentiality and integrity of email submission (email client to SMTP server) and email retrieval (email client to POP3 or IMAP server). While some of our findings are also relevant for email transport (from one SMTP server to another), the security implications in email submission and retrieval are more critical because these connections involve not only individual email messages but also user credentials that allow access to a user's email archive. We used EAST to analyze 28 email clients and 23 servers. In total, we reported over 40 STARTTLS issues, some of which allow mailbox spoofing, credential stealing, and even the hosting of HTTPS with a cross-protocol attack on IMAP. We conducted an Internet-wide scan for the particularly dangerous command injection attack and found that 320.000 email servers (2% of all email servers) are affected. Surprisingly, several clients were vulnerable to STARTTLS stripping attacks. In total, only 3 out of 28 clients did not show any STARTTLS-specific security issues. Even though the command injection attack received multiple CVEs in the past, EAST detected eight new instances of this problem. In total, only 7 out of 23 tested servers were never affected by this issue. We conclude that STARTTLS is error-prone to implement, under-specified in the standards, and should be avoided.