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Windows Server 2016 Refuses To Take Any Cumulative Updates But Takes All Other Updates Fine

I have a server that was a clean build in May of 2021.  It is server 2016 1607 running SQL 2016.  This server refuses to do *any* Microsoft Cumulative Updates.   It will do *any* other relevant Microsoft Update to this box via Windows Update without issue.   Each month the same pattern repeats on the next cumulative update.

It says it is needed.  It downloads.  It installs.  It reboots and somewhere in the boot cycle during the blue pre-desktop load when the update is working it just decides without error to return to the desktop and say that it couldn't be installed.   

I have no errors that I can find.  It just does the update, says it is done and rebooting, and then goes into that in-between state and comes out without visible errors and returns to Windows without explanation.   Everything else that either proceeded or was after it on the update list goes absolutely fine whether it needs reboots or not.   Going through May, June, July, and August it is pretty obvious that this cumulative update unable to install is a pattern and not a one-off event.   I have tried disabling SentinelOne and that did nothing.  The machine is clean of any viruses per Windows Defender/SCCM Endpoint and SentinelOne.   I have disabled all unnecessary services.  I have run a SFC/SCANNOW and it runs clean.  I have run a DISM /ONLINE /CLEANUP-IMAGE /SCANHEALTH and it runs clean.   I have blown up and re-installed Windows Update including clearing out the software database and that does nothing.   I have tried downloading cumulative updates from the Microsoft Catalog and manually applying them for a couple of months and that does nothing.  

Everything is fine except this server can't take a cumulative update.   Due to the nature of this server taking it off-line for an extended period of time is painful.  However, I am about to try an in-place upgrade to 2019 and then a clean build migration if I can't come up with what the issue is.

Any ideas as to what is going on?

Thanks so much!

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2016 adn 2019 are LTSC version.

unless your License includes software assurance the version to which each can go are limited to the release version.

I can not locate the link that discusses the limit of the two OSs that updates beyond a certain point only available to products that have/had software assurance...
you need the servicing stack updates before the cumulative updates.

These products are far from EOL
Windows Server 2019       January 9, 2024
Windows Server 2016       January 11, 2022
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every update offered is applies fine except for the cumulatives.  I am always left with one update on Windows updates  - that month's cumulative
Any ideas as to what is going on?

not until you provide either event log entries or windows update logs that reflect the error code(s)
otherwise, can't really suggest anything beyond the troubleshooting steps you have already done since you only state the update failed with no other details as to why
1. Download the update manually (google the KB number and download and apply it that way; don't do it through Windows Update).

If that fails then
2. Review the CBS logs and see what they say.  You can post them here (and someone may be able to help you review them; please don't copy and paste the text; upload the text file).  Note: the CBS logs need to be collected through PowerShell these days:

Some additional troubleshooting information:
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The latest servicing stack update was already applied as everything but cumulative applies normally eacy month.  I manually downloaded it and it evaluated and said it installed.

I have tried to download the cumulative manually each month and they fail in the same manner as the automated method in the same place.

I have attached the actual WindowsUpdate log which I pulled moments ago.WindowsUpdate.log
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Here is the CBS log file for this server
13hours after it said it needed a restart you still had not done the restart.
did you try the
 dism /online /cleanup-image /restorehealth
sfc /scannow

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i did sfc /scannow and it is fine
i did dism /online /cleanup-image /scanhealth and it said there was nothing wrong with the components.
I am not sure if it works for you, but if you stop the update service (WUAUCLT), then delete the files is directory: %windir%\SoftwareDistribution\Download . Then start the update service again.

I personally prefer to update via powershell (run as admin)
Set-ExecutionPolicy Unrestricted
install-module PSWindowsUpdate
Import-Module PSWindowsUpdate
Install-WindowsUpdate -AcceptAll

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I have stopped the services and cleared out the folder without any success.
I had never done the updates from powershell so i tried that.
same result.   I have screen shots and a new cbs log.  
It did say that it failed on SQL server 2016 CU17.  I see a lot of those automated SQL CUs fail on other servers.  I did what I always do for that which is just download it and manually apply it.  SQL Server 2016 CU17 applied effortlessly doing it that way.  The intelligence update installed fine.  It just went right back to being stuck on the August Cumulative Update which is the pattern.  Again it doesn't matter on the month I am in.  Everything else updates fine.  That month's cumulative update always fails 100% of the time *after* the restart and before the server comes back to the desk.CBS.logPB ST SQL 1 Via PS Windows Update 1.JPGPB ST SQL 1 Via PS Windows Update 2.JPGPB ST SQL 1 Via PS Windows Update 3.JPGPB ST SQL 1 Via PS Windows Update 4.JPG
Is it a Windows Cumulative Update or a SQL Server Cumulative Update? Different repair policies for either item.
Restart and retry the SQL update
Update problems can be solved by doing an in-place upgrade (mount server 2016 setup ISO in your running windows, start setup). Settings, files and programs are kept, update problems are gone. This has always worked for me. This will mean a downtime of 30-90 minutes (depending on several factors, mostly storage speed).
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Hi.  Thanks for the info.  Is there any reason to do it with the 2016 ISO vs doing it with a 2019 ISO?  If I couldn't find another way to fix this, I was planning on doing 2019 later this week in that manner.
Your last question seems odd.
2016 is where you are
I do not believe ypu can get an ISO of 2016 that incorporated the updates your system does not accept.
What is the OS build on the 2016?
2019 us an in-place upgrade.
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I am bit confused by your question back.   I thought if I did 2016 iso like it was suggested I would be downlevel, but if it fixed my Windows update issue I would just patch my way to currency.  it is 1607 completely current on all updates except whatever cumulative update is offered each month.  may failed June failed July failed august failed.  everything else installed flawlessly.   my thought was as an alternative to re-run the 2016 setup on the box, run an upgrade to 2019.  I'd snapshot the server so if it mucked up the server, I'd just say undo.
Can you get an ISO of 2016 that is a >1607 or even 1903 release?

Can you spin up a VM with 2016 Core only, see if you can get it to 1903 and then add the desktop environment using powershell tools??
I think the 2016 halts at 1607 and 2019 at 1809 or something like that...
Can you get an ISO of 2016 that is a >1607 or even 1903 release?
Those would be core versions only and also would be on the SAC rather than LTSB channels. Only available with SA

2019 is a separate product than 2016 and requires different CAL's and product keys and also is a different windows update stream
David, that's what I said, but can not locate the article, write-up that says so even though I think I read it...
Windows Server Servicing Channels  .. you have to start with SAC and not LTSC version and be enrolled in Software Assurance
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McKnife, That's what I thought.  2019 licensing is not a problem as it is a Microsoft Campus Agreement.    If there isn't a way I haven't tried to save what I have that keeps it mostly online, I might as well make the server more current.  
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the 2016 to 2019 in place upgrade went flawlessly.  the server now updated fine.  applications continue to run fine.  downtime was minimal.  thanks so much for the assistance!