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 is part of Microsoft's extended support program for legacy Windows Server systems. It's important to note that Windows Server 2008 Premium Assurance will end on January 13, 2026, while Extended Security Updates (ESU) ended on January 10, 2023. For Azure customers, ESU support ended on January 9, 2024.

General Purpose

This cumulative security update contains improvements that were previously released in KB5055609 (April 8, 2025). The update focuses on internal Windows OS functionality improvements and includes miscellaneous security enhancements. The patch is designed to maintain system security and stability for organizations still running Windows Server 2008 under Premium Assurance agreements. The update requires the latest Servicing Stack Update (SSU) KB5056457 to be installed first.

General Sentiment

The sentiment around this update appears cautious but necessary for organizations still running Windows Server 2008. While the update provides essential security improvements, there are concerns about installation requirements and potential compatibility issues. The update's timing is particularly significant given the approaching end of Premium Assurance support, and organizations are strongly encouraged to plan their migration to newer Windows Server versions.

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 2025-05-17 12:30 AM

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