Windows Server 2008R2 Update failure

Frustrated Tech 6 Reputation points
2020-12-09T14:40:16.053+00:00

Hi,

We have extended support for the above OS and I've been trying, without success, to get one of these servers updated with the latest security rollup packs but they constantly fail. All the pre-requisites have been installed successfully (KB4474419, KB4538483), as has the latest SSU - previously July but one was released this week (KB4592510) and this has also installed successfully. The ESU key has been activated successfully with slmgr /ato <ESU activation key> and confirmed that it was successful. Yet, trying to get the latest Security Monthly Quality Rollup pack (KB4592471) to install is proving impossible. The last successful pack to install was September 2020 (KB4577051). I'm now at my wits end trying to work out what is going on. Can anyone offer any ideas as to what I can do to resolve this please? Upgrading to a later version of the server OS isn't an option, as much as I would like to.

Windows Server
Windows Server
A family of Microsoft server operating systems that support enterprise-level management, data storage, applications, and communications.
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  1. Adam J. Marshall 8,801 Reputation points MVP
    2020-12-09T16:25:40.237+00:00

    Try installing the update using the LOCAL SYSTEM account (From an Administrative Command Prompt):

    psexec -SID cmd.exe
    Then use wusa.exe to install it through the command line.

    Local system should have access to everything.

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  2. Frustrated Tech 6 Reputation points
    2020-12-10T09:14:33.597+00:00

    Unfortunately, this also failed. Just to confirm, I used psexec (ran whoami to confirm it was running under NT authority\System, the update started and then failed very quickly again. I guess it's not permission related.

    I did have KB4592503 (Security Only Quality Update 2020-12) presented to me which, strangely enough, installed without issue... It's just these rollup packs that constantly fail.
    If anymore info is required, I will gladly supply as this has been plaguing me since last week now

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  3. Frustrated Tech 6 Reputation points
    2020-12-10T14:36:26.63+00:00

    Confirmed, all pre-reqs are installed - 4538483 as opposed to 4570903

  4. Dave Patrick 426.1K Reputation points MVP
    2020-12-10T14:38:31.96+00:00

    I'd verify system and servicing health by running;
    sfc /scannow

    also system update readiness tool

    https://learn.microsoft.com/en-us/troubleshoot/windows-server/deployment/fix-windows-update-errors

    Then check for errors in;
    %SYSTEMROOT%\Logs\CBS\CheckSUR.log

    --please don't forget to Accept as answer if the reply is helpful--

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