Windows Server 2016 does not install updates at scheduled time

[JWW-CSISD]

We have an OU for servers that we don't mind if they install Windows Updates and reboot nightly. For some reason, the Server 2016 servers in that OU do not automatically install updates at the time scheduled by the GPO. The settings on the servers appear to be applied correctly, and it does detect that there are updates available... it just doesn't install them at the scheduled time.

Settings from relevant Windows Update GPO:

Windows Update GPO settings

WU settings on the server:

Windows Update Settings on server

WU Restart Options on the Server:

WU Restart settings on server

WU Policy Registry settings on the server:

Any suggestions as to why this may be?

[#2 · Accepted solution]

From what you have shared, you configured everything correctly and it might be a temporary issue with the server. Try restart your server and see if the problem persist?
Are you facing the same issue with other policies too?

[#3]

@Reza_Ameri 

Hrm. Well, I just noticed that two of our 2016 servers actually HAVE installed updates recently - immediately after a scheduled task ran that rebooted them this past Saturday night. On the off chance that there's a setting the others haven't picked up since the last time the Windows Update service was started/restarted, I just restarted the wuauserv service on each of the other 2016 servers in this policy. We'll see what they do overnight tonight. If they still don't install tonight, I'll reboot them tomorrow night before the scheduled installation time and see what happens then.

As far as the our other WU polices go... the only other policy we have applied to our servers is set to "Auto download and notify to install" - not to mention none of the servers in that policy are 2016 anyway - so they're unfortunately not very relevant for troubleshooting this.

[#4]

Try to do that, if the problem persist, then look for a Windows 10 device and open the Feedback Hub app and in the category, select the Windows Server and report this issue.

[#5]

@Reza_AmeriIt looks like the restart of the wuauserv service did the trick. Thanks for the assist!

[#6]

Thank you @JWW-CSISD for the update and glad it was helpful.