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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.
ALPACA: Application Layer Protocol Confusion - Analyzing and Mitigating Cracks in TLS Authentication
(2021)
OpenPGP is one of the two major standards for end-to-end email security. Several studies showed that serious usability issues exist with tools implementing this standard. However, a widespread assumption is that expert users can handle these tools and detect signature spoofing attacks. We present a user study investigating expert users' strategies to detect signature spoofing attacks in Thunderbird. We observed 25 expert users while they classified eight emails as either having a legitimate signature or not. Studying expert users explicitly gives us an upper bound of attack detection rates of all users dealing with PGP signatures. 52% of participants fell for at least one out of four signature spoofing attacks. Overall, participants did not have an established strategy for evaluating email signature legitimacy. We observed our participants apply 23 different types of checks when inspecting signed emails, but only 8 of these checks tended to be useful in identifying the spoofed or invalid signatures. In performing their checks, participants were frequently startled, confused, or annoyed with the user interface, which they found supported them little. All these results paint a clear picture: Even expert users struggle to verify email signatures, usability issues in email security are not limited to novice users, and developers may need proper guidance on implementing email signature GUIs correctly.
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.