TY - CHAP A1 - Müller, Jens A1 - Brinkmann, Marcus A1 - Poddebniak, Damian A1 - Böck, Hanno A1 - Schinzel, Sebastian A1 - Smomrosvsky, Juraj A1 - Schwenk, Jörg T1 - “Johnny, you are fired!” – Spoofing OpenPGP and S/MIME Signatures in Emails T2 - 28th Usenix Security Symposium, Santa Clara, CA, USA N2 - OpenPGP and S/MIME are the two major standards to en-crypt and digitally sign emails. Digital signatures are sup-posed to guarantee authenticity and integrity of messages. Inthis work we show practical forgery attacks against variousimplementations of OpenPGP and S/MIME email signatureverification in five attack classes: (1) We analyze edge casesin S/MIME’s container format. (2) We exploit in-band sig-naling in the GnuPG API, the most widely used OpenPGPimplementation. (3) We apply MIME wrapping attacks thatabuse the email clients’ handling of partially signed mes-sages. (4) We analyze weaknesses in the binding of signedmessages to the sender identity. (5) We systematically testemail clients for UI redressing attacks.Our attacks allow the spoofing of digital signatures for ar-bitrary messages in 14 out of 20 tested OpenPGP-capableemail clients and 15 out of 22 email clients supportingS/MIME signatures. While the attacks do not target the un-derlying cryptographic primitives of digital signatures, theyraise concerns about the actual security of OpenPGP andS/MIME email applications. Finally, we propose mitigationstrategies to counter these attacks. Y1 - 2019 UR - https://www.usenix.org/conference/usenixsecurity19/presentation/muller EP - 18 ER - TY - CHAP A1 - Müller, Jens A1 - Brinkmann, Marcus A1 - Poddebniak, Damian A1 - Schinzel, Sebastian A1 - Schwenk, Jörg T1 - What's up John­ny? – Co­vert Con­tent At­tacks on Email End-to-End En­cryp­ti­on T2 - 17th In­ter­na­tio­nal Con­fe­rence on Ap­p­lied Cryp­to­gra­phy and Net­work Se­cu­ri­ty (ACNS 2019) N2 - 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. Y1 - 2019 SP - 1 EP - 18 ER -