WSUS not updating Win10 to 1909

dasmail2000 used Ask the Experts™
I need some help here to understand why our WSUS implementation is not updating Win 10 1809 to 1903 or 1909. You can see in the attached screenshots that the updates are approved for install but they simply will not install. I have gone through all I can find about this so finally thought I's throw up a hail-mary here to see if someone can shed some light.

In the attached screenshots, you will see that the required updates are approved for installation, but their status is "downloaded". I am not sure what that means and I have been unable to find out too :/

Thanks in advance and please let me know if there is any info you need.

WSUS - on a Win2019 Server
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Distinguished Expert 2018

So what happens at the client, is the update even detected?
You could deploy the enablement package by using a scheduled task and be done with.


Enablement package won't get the PCs from 1809 though - only those on 1903 will get to 1909.

As to what happens on the client - hard to say if it detects the update in the automated process. However, if I run an update manually on a PC, it does detect the update is needed and does pull it from WSUS.


Correction here - on a different PC I just did a manual Windows Update and it came back listing the updates that are needed (1903 CU, 1903, 1909 and another 1909 feature update). However, they all have a status of "Pending install". Again, I am at a loss as to why that could be so if anyone has a thought - please hit me with it.

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The update shown in your screen capture isn't an update from 1809 to 1903.  It's a special update for Windows 10 1903 workstations to activate some of the features of 1909 (without actually updating to 1909).  Take a look at this article:
Distinguished Expert 2018

"Enablement package won't get the PCs from 1809 though - only those on 1903 will get to 1909" - sure, I misread that.
What I would do, since I dislike to use WSUS for this, anyway, is get the 1909 ISO file, extract it to a share and deploy a scheduled task:
\\server\share\setup.exe /auto upgrade /dynamicupdate disable

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and that's it.

You could even enable time randomization of execution in the task, if bandwidth is a concern.
I do feature updates through WSUS, but I've found that it doesn't work well to combine security/cumulative updates to the existing OS version with a feature update.  My experience is that the workstations won't install the feature update until the security updates for the older OS have been installed and the workstation restarted. At times I've seen similar behavior as you've described such that the workstation can't install any updates when the feature update is mixed in with regular updates. Because of the way Windows Update works in Windows 10, it seems that the OS wants to install all the updates or none.  

So, I create a separate update group in WSUS for feature updates.  Then I manage the updates so that the workstations are updated with the most recent security/cumulative updates first. After that's done and they've restarted, I move them to the feature update group and approve the feature update for that group only.  That may not be the most elegant solution but it works.
Thanks for your inputs but the issue seems to be resolved. The 'fix' was to set a deadline for the updates in WSUS. Once that happened everything got pushed out and all seems good. I do have to check a few more but the first four look good.

I do use separate groups to stage the updates - thanks for sharing your thoughts as is helps validate our process.

I like that idea for the enablement update - will have to try that out.

Thanks to you both for your time and input.

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