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Managed to isolate the cause after performing some rescuing via SSM. The issue seems to stem from the upgrade from the CPU generation leap.
I had always thought each component, Storage, Compute, and Networking are separate, but the ENI config was lost during the upgrade, so the server had trouble (i.e. did not know where the DNS server is) contacting the DCs for authentication. Without this link to the DCs, NLA will never be met.
So if you are going to upgrade to the latest generation.
- While on the current instance type (while you can RDP to the EC2 instance), navigate to System Properties and go to the Remote tab.
- Untick the NLA option and apply and save the change.
- Shutdown the instance and change to the desired instance type.
- RDP to the instance using the Administrator account.
- Here you will see that the network interface configuration is empty, so add your DNS server IP address back in here.
- Confirm you have a connection to the DCs by pinging or something of the sort, then repeat step 1, but this time enable the NLA option and save.
Reboot and Voilà, you should now have access to the EC2 instance using your domain logins again.
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