KB5055609: Overview with user sentiment and feedback
Last Updated April 19, 2025
Probability of successful installation and continued operation of the machine
Overview
KB5055609 is a Monthly Rollup update for Windows Server 2008 Premium Assurance customers. This update is significant as it comes near the end of the support lifecycle for Windows Server 2008, with Premium Assurance support ending on January 13, 2026. The update includes security improvements and requires the latest Servicing Stack Update (SSU) KB5056457 as a prerequisite for installation.
General Purpose
This cumulative security update addresses vulnerabilities and includes improvements from previous updates. A key security enhancement involves changes to the system drive's inetpub folder creation, which is implemented regardless of whether Internet Information Services (IIS) is enabled. This change is part of security improvements addressing CVE-2025-21204. The update requires careful attention to prerequisites, particularly the installation of the latest Servicing Stack Update, as failure to do so will prevent the update from being offered or installed.
General Sentiment
The sentiment around this update appears cautious but necessary. While it provides important security improvements, there are notable installation requirements and potential issues that administrators need to be aware of. The update's timing near the end of Windows Server 2008's support lifecycle adds complexity to the decision-making process for administrators. The requirement for Premium Assurance and specific prerequisites like the SSU installation suggests careful planning is needed for successful deployment.
Known Issues
- After installing and restarting, devices may receive the error "Failure to configure Windows updates. Reverting Changes."
- Update may show as Failed in Update History
- Installation issues may occur if Premium Assurance is not properly activated
- Problems may arise if the latest SSU (KB5056457) is not installed first
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 2025-04-19 06:55 AM