Mitigation of Attacks on Email End-to-End Encryption OpenPGP and S/MIME are two major standards for securing email communication introduced in the early 1990s. Three recent classes of attacks exploit weak cipher modes (EFAIL Malleability Gadgets, or EFAIL-MG), the flexibility of the MIME email structure (EFAIL Direct Exfiltration, or EFAIL-DE), and the Reply action of the email client (REPLY attacks). Although all three break message confidentiality by using standardized email features, only EFAIL-MG has been mitigated in IETF standards with the introduction of AEAD algorithms. So far, no uniform and reliable countermeasures have been adopted by email clients to prevent EFAIL-DE and REPLY attacks. Instead, email clients implement a variety of different ad-hoc countermeasures which are only partially effective, cause interoperability problems, and fragment the secure email ecosystem.We present the first generic countermeasure against both REPLY and EFAIL-DE attacks by checking the decryption context including SMTP headers and MIME structure during decryption. The decryption context is encoded into a string DC and used as Associated Data (AD) in the AEAD encryption. Thus the proposed solution seamlessly extends the EFAIL-MG countermeasures. The decryption context changes whenever an attacker alters the email source code in a critical way, for example, if the attacker changes the MIME structure or adds a new Reply-To header. The proposed solution does not cause any interoperability problems and legacy emails can still be decrypted. We evaluate our approach by implementing the decryption contexts in Thunderbird/Enigmail and by verifying their correct functionality after the email has been transported over all major email providers, including Gmail and iCloud Mail. 1647–1664 1647–1664 Association for Computing Machinery