Windows server 2008 R2 servers going into recovery mode after applying Nov-Dec 2019 patches

Hi All, we have recently patches 4 of the Windows 2008R2 servers. The patches which we pushed from bigfix were the patches released in November and December 2019. When the patches get completed onto the system and when we reboot the system the system goes into recovery mode.

Below are the KB which were pushed onto the Windows 2008R2 servers:

KB4520003
KB4525233
KB4530692

Does any one have come across this issue.

This is not a BigFix issue but an Operating System.
We are having same issues with Windows 2008 Servers in general after applying patches. The final solution for this is to migrate to a supported version of Windows.

We experienced this with 1 server running 2008 and 1 running 2008R2. We followed these steps to fix it:

The issue might occur due to the changes in the winload.exe file location. Please try the below-mentioned steps which help to resolve the issue.

  1. Boot the server either in recovery console or boot via disabling driver signature off (command ‘bcdedit /set {default} nointegritychecks ON’).
  2. Run the following command to change the winload.exe path i.e bcdedit /set {default} path \windows\system32\winload.exe
  3. Once done then reboot the server by turning on driver signing. To enable device driver signing, type “BCDEDIT /set nointegritychecks OFF” then press “Enter“

https://borncity.com/win/2019/12/11/patchday-updates-for-windows-7-8-1-server-dec-10-2019/

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We experienced the same issue on 2008R2 servers that require KB 4474419 patch (OCT or Sept month). if the servers that have issues require Sept or Oct month KB 4474419 then install this patch first, reboot the server and then try installing Nov and Dec month patches.

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Thanks you guys for the reply, i will surely start with the process which which you have shared and will share the results.

Any luck applying the KB4474419 patch and then new patches? One of my customers has come across this issue the last 3 months and my suspicions are leading me to believe the KB4474419 patch is needed.

This has happened to about 30 servers each month, it seems some Windows 2008 / Windows 2008 R2 servers do not have this issue even if they don’t have the KB4474419 patch - so different from system to system.

Any shares in findings would be appreciated.

Hi @ptholt79 we are facing the same issue and yet we are not able to find out the main root cause.

Any luck determining root cause? We’ve stood up 2008 test servers and cloned a server that had the issue and reissued the monthly baseline and haven’t been able to reproduce the issue.

Hi @ptholt79 We have not found the root cause but we have resolved the issue on maximum systems. Out of 100 systems we were able to patch 60 systems successfully with out any error, after deploying service stack, sha256 and the security updates on the Windows 2008 R2 servers.

But still we are facing issue on few of the systems. Now we have started getting -2146885628 exit code.

Has anyone tried researching the issue on the PatchManagement.org mailing list archives?

They are usually a pretty good source of information regarding Windows patching issues.

I will try that @TimRice . I believe we may have resolved the issue in our customer’s environment as well.

We were able to reproduce the issue on a server that we had previously identified as having the issue. When sending the monthly baseline with KB4474419 in it, the machine still failed and needed recovery after attempting to install the monthly rollup. It wasn’t until we manually installed KB4474419 by itself, rebooted, applied KB4534310, and rebooted again, the server was operating properly without failure. I had suspected that the monthly rollups were failingbecause KB4474419 was missing from the 2008 servers, turns out that assumption was right.

Hope this helps someone.

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Hi @ptholt79 were you patches getting failed even after deploying KB4474419 on the 2008 r2 servers? I am facing this issue in my environment, the KB4474419 is successfully completed on few of the systems by when we are trying to push patches on those system its getting failed. Not on all the 2008 / 2008 r2 servers but on few of them.

We have not seen any issue as of yet after installing KB4474419 @karthik04 , but if we do, I will update here.