Hi @Sukant Virkud ,
As a basic troubleshooting, if possible I would recommend to login to the server and manually scan for updates to check whether you see the same error in server or to diagnose and troubleshoot the issue in a better way, I would recommend to capture network trace, collect the logs with the help of this package, install and execute Collect-AMALogs runbook and analyze the logs.
In general, the error code 0x80072F8F seems to be related to either windows activation failure or proxy settings or firewall issue or ssl certificate i.e., may be due to one of the below 4 reasons:
- verify the date or time of the server as when windows tries to verify the SSL certificate for windows update, the time skew results in the certificate validation failing
- rules configured in Azure Update Management might be preventing the access to server so try by adding below URLs in trusted sites or in other words whitelisting below endpoints at proxy level
- proxy didn't allow the connection with "xxxxxx.windowsupdate.com" which contains the trusted root cert list so TLS handshake is not established and certification verification failure when validating "sls.update.microsoft.com" so to resolve the issue, update proxy configuration to allow *.windowsupdate.com traffic
- update agent was unable to update service due to certificate error so open required port in firewall
Check if your issue is due to one of these reasons. If not, to try diagnosing and troubleshooting the exact cause of this kind of issue, it would require deep dive with the help of related environment trace logs, etc. So for that, I would recommend to raise a technical support request if you have a support plan. But if you don't have a support plan then please send an email to AzCommunity@microsoft.com with subject being "Attn:Krishna" and your subscription ID and this question's link in the body of the email so that my team will work with you via our technical support channel.