Windows Server 2019 Updates Install but Fail After Restart
Asked by
MellowOtter42
I manage around 30 Windows Server 2019 machines and use SCCM to deploy the monthly cumulative updates and patches. Recently, some updates appear to install completely, but the servers fail when they restart to finish applying them. I've already tried running SFC, clearing the SoftwareDistribution folder, and removing the CCMCache contents, but the problem continues. Is anyone else seeing this, and has anyone found a reliable fix or workaround?
Answers
The September out-of-band update installed normally in our environment, so the failure may depend on the exact cumulative update, server configuration, or update-management infrastructure.
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There have been several reports of broken Windows Server 2019 updates. If you’re running Sophos or another endpoint-security product, temporarily reviewing its update-blocking or tamper-protection events may be useful. Also compare the failing servers with the ones that install successfully and check the CBS and Windows Update logs for the rollback error.
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There may be an issue with the specific update being offered. Microsoft replaced KB5122876 with KB5129238 because of reported Remote Desktop Services problems. We’re seeing similar failures on a few of our servers through WSUS, although we haven’t confirmed a fix yet. The .NET update did install successfully when applied manually, so downloading and installing the affected package directly may be worth trying.
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Windows Server 2019 is still supported for several more years, so replacing the operating system isn’t really a solution to this particular problem. I’d focus on identifying the exact KB that fails and checking whether security software or the update service is interfering.
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Try the built-in Windows Update Troubleshooter as well. It has surprisingly helped with update problems on some servers, even though it isn’t consistently effective.
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MellowOtter42: I’ve tried it before and it hasn’t helped in my environment, but I may run it again while checking the servicing logs.