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 builds upon previous updates, specifically incorporating improvements from KB5055609 released in April 2025.

General Purpose

The primary purpose of this update is to provide security improvements to internal Windows OS functionality. It aims to address various security vulnerabilities and enhance system protection for Windows Server 2008 systems still under Premium Assurance support. The update is part of Microsoft's ongoing commitment to providing security updates for systems under extended support agreements, helping organizations maintain security compliance while they plan their migration to newer Windows Server versions.

General Sentiment

The sentiment around this update appears cautious but necessary. While it provides essential security improvements, there are concerns about installation requirements and potential issues. The update requires specific prerequisites, including the latest Servicing Stack Update (SSU KB5056457), which must be installed first. Organizations need to verify their Premium Assurance status and ESU MAK add-on key activation before attempting installation. The update's timing, coming close to the end of Premium Assurance support, suggests organizations should be actively planning their migration strategies.

Known Issues

• After installation and restart, users might 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 running an edition not supported 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 08:06 AM

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