Unable to RDP into Windows server 2019 (AWS EC2 instance) after reboot after updating with KB5013941

Question

Hello,

We have recently trying to upgrade our Windows 2019 servers (AWS EC2 instance) to May 2022 packages : KB5013941
The upgrade seems to be successful.

But once we install some of our custom applications like .NET , putty etc, we issue a reboot command.
That is typically issued using a Chef command

reboot "Migration_reboot" do
  action :request_reboot
  reason "Need to reboot ." 
  ignore_failure false
  retries 3
end

Once this issue is command, the system used to get rebooted successfully previoulsy.

But since the new May 2022 update KB5013941, the system gets stuck in a reboot loop.
All we can see from the instance screenshot after reboot cmd is triggered, is a black screen with load symbol and since it is stuck in that loop, we are not able to RDP to it and finish the workflow.
Nothing in system logs of AWS, nothing much in Windows event viewer logs after restart (force stop and start)

We do have a workaround where when this instance is stuck in reboot loop, we force stop the instance from AWS (which takes 3+ mins, that's usually 30 seconds generally for normal Windows instances) and start it again.

But this has become a blocker since we cannot finish the workflow and have to manually restart instance from AWS every time.
We have also tried to upgrade to following patches. The reboot loop with black screen and loading icon still exists...

1. May 19, 2022—KB5015018 (OS Build 17763.2931) Out-of-band
2. May 24, 2022—KB5014022 (OS Build 17763.2989) Preview

Can you please help us with more information on why this might happen. We're happy to get any files, logs if needed

Answer 1

Hi, @Divya Ranjanagi

Can I access Windows Server after rebooting?
You can use EC2Rescue for Windows Server to analyze EC2 issues.

https://docs.aws.amazon.com/AWSEC2/latest/WindowsGuide/Windows-Server-EC2Rescue.html