- 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.
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