TY - CHAP A1 - Ising, Fabian A1 - Poddebniak, Damian A1 - Kappert, Tobias A1 - Saatjohann, Christoph A1 - Schinzel, Sebastian T1 - Content-Type: multipart/oracle -- Tapping into Format Oracles in Email End-to-End Encryption T2 - 32nd USENIX Security Symposium N2 - 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 net work 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. Y1 - 2023 UR - https://www.usenix.org/conference/usenixsecurity23 PB - USENIX Association ER -