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2025-10 Cumulative Update for Windows Server 2019 (KB5066586) Undoes Update on Reboot
We have a Windows Server 2019 Standard which will not install the 2025-10 Cumulative Update for Windows Server 2019 (KB5066586) update. The installation part goes fine, but when the server is reboot...
Hello Michael2000.
Your action plan covers most of the possible causes so if still the same, I do not think there's much you can do (maybe, some package that became corrupt leading to the actual scenario).
Only thing left is to double-check if following scenario applies: https://learn.microsoft.com/en-us/troubleshoot/windows-client/performance/windows-devices-fail-boot-after-installing-kb4041676-kb4041691
Thank you for your response. Unfortunately, the article does not apply to what I am experiencing. The system is not having trouble rebooting. It reverses the installation of the Cumulative Update on reboot.