Windows 11 24H2 & Windows Server 2025: Key Security and Management Updates for CISOs

Microsoft's recent updates to Windows 11 version 24H2 and Windows Server 2025 introduce several features and enhancements aimed at bolstering security and improving system management. However, some of these additions necessitate careful evaluation to ensure they align with organizational security policies. Chief Information Security Officers (CISOs) should be particularly attentive to the following developments:

Recall: Balancing Innovation with Privacy Concerns​

The introduction of the Recall feature in Windows 11 has sparked significant debate within the cybersecurity community. Designed to capture and store snapshots of user activity to facilitate comprehensive search functionality, Recall has been criticized as a potential "privacy nightmare." In response to these concerns, Microsoft has implemented several safeguards:

• Opt-In Mechanism: Recall is disabled by default, requiring users to actively enable it during system setup.
• Data Encryption: Snapshots are encrypted using the device's Trusted Platform Module (TPM), ensuring that sensitive information remains protected.
• User Control: Users can manage data retention periods, exclude specific applications or websites from being recorded, and delete stored snapshots as needed.

Despite these measures, organizations must assess the implications of deploying Recall within their environments. The University of Pennsylvania's Information Systems & Computing department, for instance, has chosen to disable Recall on managed systems due to unresolved security and privacy concerns. They recommend that administrators of other Windows environments consider similar actions. (isc.upenn.edu)

Hotpatching: Enhancing Security Without Downtime​

Windows Server 2025 introduces hotpatching, a feature that allows critical security updates to be applied without necessitating system restarts. This advancement offers several benefits:

• Reduced Downtime: By eliminating the need for reboots, hotpatching minimizes service interruptions, thereby maintaining operational continuity.
• Accelerated Security Response: Organizations can deploy security patches more swiftly, reducing the window of vulnerability to potential exploits.

While hotpatching presents clear advantages, it's essential for IT teams to thoroughly test this feature within their specific environments to ensure compatibility and effectiveness.

Addressing Authentication Challenges​

Recent updates have also addressed critical authentication issues:

• Windows Hello Authentication Failures: The KB5055627 update resolves problems where Windows Hello failed to authenticate users after system resets, a concern particularly relevant in environments relying on biometric authentication. (redteamnews.com)
• Kerberos Authentication Issues: Post-update, some Active Directory Domain Controllers experienced difficulties processing Kerberos logons using certificate-based credentials. Microsoft has acknowledged this issue and is working on a resolution. (learn.microsoft.com)

Organizations should monitor these developments closely and apply patches as they become available to maintain secure authentication processes.

Compatibility and Deployment Considerations​

The deployment of Windows 11 24H2 has revealed compatibility challenges:

• CIS Benchmark Configurations: Implementing certain Center for Internet Security (CIS) Level 1 Benchmarks, such as disabling OneSettings downloads, has led to upgrade failures. This underscores the need for careful configuration management during system upgrades. (checkyourlogs.net)
• Application Compatibility: Issues have been reported with applications like AutoCAD 2022 and certain versions of Easy Anti-Cheat, leading to system instability or application failures. Microsoft has applied compatibility holds to prevent affected devices from updating until these issues are resolved. (learn.microsoft.com)

CISOs should ensure that thorough testing is conducted before deploying these updates across enterprise environments to mitigate potential disruptions.

Strengthening Credential Protection​

Microsoft continues to enhance credential security:

• Windows Hello Enhancements: The integration of passkey support and the use of Windows Hello to protect features like Recall and Personal Data Encryption (PDE) demonstrate a commitment to robust authentication mechanisms. (blogs.windows.com)
• App Control Policies: The introduction of App Control for Business allows organizations to enforce policies that ensure only verified applications run on devices, reducing the risk of malicious software execution.

Implementing these features can significantly bolster an organization's defense against credential theft and unauthorized access.

Conclusion​

The latest updates to Windows 11 and Windows Server 2025 offer promising advancements in security and system management. However, they also introduce complexities that require careful consideration. CISOs must balance the adoption of new features with the potential risks they pose, ensuring that security policies are updated accordingly and that thorough testing is conducted prior to widespread deployment. By staying informed and proactive, organizations can leverage these updates to enhance their security posture while maintaining operational integrity.

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Source: csoonline.com Securing Windows 11 and Server 2025: What CISOs should know about the latest updates