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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,
Start by stopping non-Microsoft services with MSCONFIG.
Stop and disable SQL Server-type services.
Check if you have any unknown profiles in "Advanced system settings" -> User Profiles -> Settings.
If you have any, delete them.
Reboot your server.
Try installing your updates again.
That's it.