CVE-2014-5239 in Outlook.com
Summary
by MITRE
The Microsoft Outlook.com application before 7.8.2.12.49.7090 for Android does not verify X.509 certificates from SSL servers, which allows man-in-the-middle attackers to spoof servers and obtain sensitive information via a crafted certificate.
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Analysis
by VulDB Data Team • 03/28/2022
The vulnerability identified as CVE-2014-5239 represents a critical security flaw in Microsoft Outlook.com's Android application prior to version 7.8.2.12.49.7090. This issue stems from the application's failure to properly validate X.509 certificates during SSL/TLS connections, creating a significant attack vector for malicious actors. The vulnerability falls under the category of weak certificate validation, which is classified as CWE-295 in the Common Weakness Enumeration catalog, specifically addressing improper certificate validation. The flaw enables attackers to perform man-in-the-middle attacks by presenting forged SSL certificates that appear legitimate to the vulnerable application.
The technical implementation of this vulnerability occurs at the SSL/TLS handshake level within the Android application's network security stack. When Outlook.com attempts to establish secure communication with Microsoft's servers, the application fails to perform proper certificate chain validation, certificate signature verification, or hostname matching against the presented certificate. This incomplete certificate verification process allows attackers to intercept communications and present malicious certificates that the application accepts without proper scrutiny. The vulnerability essentially disables the certificate pinning mechanism that should protect against certificate impersonation attacks, making it possible for attackers to establish fraudulent secure connections.
The operational impact of this vulnerability extends beyond simple data interception, as it enables attackers to obtain sensitive user information including email content, account credentials, and personal data transmitted through the compromised application. Attackers can leverage this weakness to perform session hijacking, credential theft, and data exfiltration from users who are unaware of the compromised connection. The vulnerability is particularly dangerous in public Wi-Fi environments where attackers can easily intercept network traffic and exploit the missing certificate validation. According to ATT&CK framework, this vulnerability maps to T1046 (Network Service Scanning) and T1566 (Phishing) techniques, as attackers can combine this weakness with social engineering to create convincing fraudulent email services.
Mitigation strategies for CVE-2014-5239 require immediate application updates to version 7.8.2.12.49.7090 or later, which implements proper X.509 certificate validation. Organizations should also consider implementing additional network security controls such as SSL/TLS inspection tools and certificate transparency monitoring to detect and prevent the use of fraudulent certificates. Network administrators should monitor for suspicious certificate issuance patterns and implement certificate pinning policies where possible. The vulnerability highlights the importance of proper cryptographic implementation and the necessity of following security best practices outlined in NIST SP 800-52 for certificate management and validation. Users should be educated about the risks of connecting to untrusted networks and the importance of keeping applications updated to prevent exploitation of known vulnerabilities.