Windows Server 2022 Activation Failed

Have you deployed Windows Server 2022 Datacenter Edition from the marketplace but ended up in Activation error? This blog will tell you the fix for that problem!

The Problem

You have a Windows Server 2022 created from Azure Marketplace image but its not getting activated and you are seeing the following error while trying to activate it manually from Settings:

Possible Causes

There are some possible causes which are highlighted by Microsoft and experienced by customers:

• The IMDS (Azure Instance Metadata Service) is not getting connected from inside the machine. There is a script by Microsoft to validate this.
• System certificates which are used by the IMDS services are expired. There was a recent announcement by Microsoft for changes in the CAs. Check that email and read carefully for any change that needs to be done on CAs. There is also a script provided by Microsoft to check for any certificate missing for IMDS. If you find any certificate missing, you can install them manually from here.
• Firewall or any proxy blocking the IMDS communication. You must make sure your firewalls or proxy are not blocking the outbound communication to 169.254.169.254 and URL http://169.254.169.254/metadata/instance
• Missing KB update that needs to be installed (KB5036909) in your Windows Server 2022

Solution

In my case, the problem was fixed in two parts:

I ran the missing certificates script provided by Microsoft and found few which I installed on the machine manually and ran the following command in CMD as Admin.

I restarted the machine and it worked! The problem was gone BUT i kept it under-monitoring for next 3-4 days and unfortunately, the problem raised again 🙁

I was again seeing the same error while trying to activate the machine from Windows Settings.

Then I found out with the help of Microsoft Support engineer that there is a dependent KB article which has a fix for NTLM issues found in the required Missing KB update that needs to be installed (KB5036909). The dependent KB5037782 was then installed and restarted the machine.

The issue was fixed after the reboot and once again I kept it under-monitoring and fortunately this time, it never happened again! pheww.

Hope this article will help you if you ever face this issue on your Windows Server 2022 Datacenter edition created from Azure marketplace.