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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.
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.
Vulnerabilities in private networks are difficult to detect for attackers outside of the network. While there are known methods for port scanning internal hosts that work by luring unwitting internal users to an external web page that hosts malicious JavaScript code, no such method for detailed and precise service identification is known. The reason is that the Same Origin Policy (SOP) prevents access to HTTP responses of other origins by default. We perform a structured analysis of loopholes in the SOP that can be used to identify web applications across network boundaries. For this, we analyze HTML5, CSS, and JavaScript features of standard-compliant web browsers that may leak sensitive information about cross-origin content. The results reveal several novel techniques, including leaking JavaScript function names or styles of cross-origin requests that are available in all common browsers. We implement and test these techniques in a tool called CORSICA. It can successfully identify 31 of 42 (74%) of web services running on different IoT devices as well as the version numbers of the four most widely used content management systems WordPress, Drupal, Joomla, and TYPO3. CORSICA can also determine the patch level on average down to three versions (WordPress), six versions (Drupal), two versions (Joomla), and four versions (TYPO3) with only ten requests on average. Furthermore, CORSICA is able to identify 48 WordPress plugins containing 65 vulnerabilities. Finally, we analyze mitigation strategies and show that the proposed but not yet implemented strategies Cross-Origin Resource Policy (CORP)} and Sec-Metadata would prevent our identification techniques.
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.