KB5058449: Overview with user sentiment and feedback

Overview

KB5058449 is a Monthly Rollup security update for Windows Server 2008 Premium Assurance customers scheduled for release on May 13, 2025. This update comes as Windows Server 2008 approaches its end of support, with Premium Assurance support ending on January 13, 2026. The update contains important security improvements and follows the April 2025 security update (KB5055609).

General Purpose

The primary purpose of this update is to provide security improvements to internal Windows OS functionality. It builds upon previous security updates and is part of Microsoft's ongoing commitment to protect Windows Server 2008 systems through their extended support period. The update specifically focuses on addressing miscellaneous security vulnerabilities within the internal Windows OS components, though specific details about these improvements are not publicly disclosed.

General Sentiment

The sentiment around this update appears cautious but necessary. While it's a critical security update for systems still running Windows Server 2008, there are important considerations regarding installation requirements and potential issues. Users should note that this is one of the final updates before Windows Server 2008 Premium Assurance support ends, highlighting the urgency for organizations to plan their migration to newer Windows Server versions. The update requires specific prerequisites, including the latest Servicing Stack Update (SSU), which adds complexity to the installation process.

Known Issues

• After installing and restarting, users may receive the error "Failure to configure Windows updates. Reverting Changes"
• Update may show as Failed in Update History
• Installation issues may occur if the device is not running a supported edition for ESU
• Problems may arise if ESU MAK add-on key is not properly installed and activated

Disclaimer: We take measures to ensure that AI-generated content is of the highest possible quality, but we cannot guarantee its accuracy and recommend that users do their own independent research. Generated on 2025-06-29 02:00 AM

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