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For anyone finding this in the future, this specific issue was that my us-east-1b happened to be one of the availability zones not supported by Workspaces. I added a third AZ in us-east-1c and was able to register the directory. I'm now running into other issues trying to create a workspace but that is outside the scope of this question.
The only way to avoid this issue is to look up what AZ's are supported for Workspaces here: https://docs.aws.amazon.com/workspaces/latest/adminguide/azs-workspaces.html
and then cross-reference that against your specific AZ mapping listed under "Your AZ ID" here: https://us-east-1.console.aws.amazon.com/ram/home?region=us-east-1#Home:
If you don't have at least 2 subnets in supported AZ's you'll have to add more subnets to your VPC in order to get this to work. Use caution though when doing this since adding subnets can cause issues with existing resources like API Gateway VPC Links, CodeBuild Projects with VPC access, etc; especially if you're managing your resources via IaC (terraform, cloudformation, cdk, etc.). In my case, I had to make changes to my cdk code to constrain the existing resources to the existing subnets making the new subnet really only usable for Workspaces or other future resources.
Assuming all the VPC is configured correct with subnets, route tables etc., I would pivot back to cloudtrail events at the time of Simple AD creation and debug. By default Simple AD creates the config in single AZ at the time of creation.
Also, file a AWS Support case so that the team can help validate the backend events and if something changed in course of time. If its not too much work, I would rather create simple AD again registered with 2 AZs.
I know this doesnt give concrete answers you are looking for, but sharing thoughts if you havent considered above. Just with the facts provided in the question, it would be hard to validate and provide answers on why only 1 AZ shows up.
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