Open Access

We show practical attacks against OpenPGP and S/MIMEencryption and digital signatures in the context of email. Instead of tar-geting the underlying cryptographic primitives, our attacks abuse legiti-mate features of the MIME standard and HTML, as supported by emailclients, to deceive the user regarding the actual message content. Wedemonstrate how the attacker can unknowingly abuse the user as a de-cryption oracle by replying to an unsuspicious looking email. Using thistechnique, the plaintext of hundreds of encrypted emails can be leakedat once. Furthermore, we show how users could be tricked into signingarbitrary text by replying to emails containing CSS conditional rules.An evaluation shows that "out of" OpenPGP-capable email clients,as well as "out of" clients supporting S/MIME, are vulnerable to atleast one attack. We provide different countermeasures and discuss theiradvantages and disadvantages.

OpenPGP and S/MIME are the two major standards for email end-to-end encryption. We show practical attacks against both encryption schemes in the context of email. First, we present a design flaw in the key update mechanism, allowing a third party to deploy a new key to the communication partners. Second, we show how email clients can be tricked into acting as an oracle for decryption or signing by exploiting their functionality to auto-save drafts. Third, we demonstrate how to exfiltrate the private key, based on proprietary mailto parameters implemented by various email clients. An evaluation shows that 8 out of 20 tested email clients are vulnerable to at least one attack. While our attacks do not target the underlying cryptographic primitives, they raise concerns about the practical security of OpenPGP and S/MIME email applications. Finally, we propose countermeasures and discuss their advantages and disadvantages.

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.

S/MIME and OpenPGP use cryptographic constructions repeatedly shown to be vulnerable to format oracle attacks in protocols like TLS, SSH, or IKE. However, format oracle attacks in the End-to-End Encryption (E2EE) email setting are considered impractical as victims would need to open many attacker-modified emails and communicate the decryption result to the attacker. But is this really the case? In this paper, we survey how an attacker may remotely learn the decryption state in email E2EE. We analyze the interplay of MIME and IMAP and describe side-channels emerging from network patterns that leak the decryption status in Mail User Agents (MUAs). Concretely, we introduce specific MIME trees that produce decryption-dependent network patterns when opened in a victim’s email client. We survey 19 OpenPGP- and S/MIME-enabled email clients and four cryptographic libraries and uncover a side-channel leaking the decryption status of S/MIME messages in one client. Further, we discuss why the exploitation in the other clients is impractical and show that it is due to missing feature support and implementation quirks. These unintended defenses create an unfortunate conflict between usability and security. We present more rigid countermeasures for MUA developers and the standards to prevent exploitation.