CVE-2010-1568 in Ironport Desktop Flag Plugin For Outlook
Summary
by MITRE
The Send Secure functionality in the Cisco IronPort Desktop Flag Plug-in for Outlook before 6.5.0-006 does not properly handle simultaneously composed messages, which might allow remote attackers to obtain cleartext contents of e-mail messages that were intended to be encrypted, aka bug 65623.
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Analysis
by VulDB Data Team • 09/13/2021
The vulnerability identified as CVE-2010-1568 affects the Cisco IronPort Desktop Flag Plug-in for Microsoft Outlook, specifically versions prior to 6.5.0-006. This security flaw resides within the Send Secure functionality that is designed to encrypt email communications. The issue manifests when multiple email messages are composed simultaneously within the Outlook environment, creating a race condition that compromises the intended encryption process. The vulnerability represents a critical weakness in the cryptographic implementation of email security within the Microsoft Outlook ecosystem, potentially undermining the confidentiality assurances that users expect from encrypted email communications.
The technical root cause of this vulnerability stems from improper handling of concurrent message composition processes within the IronPort plug-in. When users compose multiple emails simultaneously, the plug-in fails to correctly manage the encryption state transitions between these messages. This flaw allows attackers to intercept cleartext versions of emails that were meant to be encrypted, effectively bypassing the security controls designed to protect sensitive information. The issue is classified as a race condition vulnerability where the timing of message composition and encryption operations creates an exploitable window. According to CWE classification, this corresponds to CWE-362, which describes Race Conditions that can lead to security vulnerabilities when multiple threads or processes access shared resources without proper synchronization mechanisms.
The operational impact of CVE-2010-1568 extends beyond simple information disclosure, as it fundamentally undermines the trust model of secure email communications. Attackers can leverage this vulnerability to access sensitive business communications, personal information, and potentially confidential corporate data that was intended to remain encrypted. The vulnerability affects organizations that rely on IronPort's encryption capabilities for compliance with data protection regulations and internal security policies. The flaw is particularly dangerous in environments where sensitive communications are routine, such as financial services, healthcare organizations, or legal firms where email encryption is critical for maintaining confidentiality. This vulnerability aligns with ATT&CK technique T1566, which covers credential access through social engineering and manipulation of communication tools, though in this case the manipulation occurs through a technical flaw rather than social engineering.
Organizations should prioritize immediate remediation by updating to Cisco IronPort Desktop Flag Plug-in version 6.5.0-006 or later, which contains the necessary patches to address the race condition in message composition handling. Security administrators should also implement monitoring for unusual email activity patterns that might indicate exploitation attempts, particularly around the time when multiple messages are composed simultaneously. Additional mitigations include reviewing and strengthening email security policies to ensure that sensitive information is not transmitted through unpatched systems, and considering alternative encryption methods for highly sensitive communications. The vulnerability highlights the importance of proper synchronization mechanisms in security-critical applications and serves as a reminder of the potential consequences when cryptographic implementations fail to account for concurrent processing scenarios. Organizations should also conduct vulnerability assessments to identify other potentially affected systems and ensure comprehensive patch management processes are in place to prevent similar issues from arising in the future.