In the Windows FAQ (https://aws.amazon.com/windows/faq/), the following is mentioned:
How can I use my own Windows Server license on EC2 instances with a default tenancy?
You should use your own Windows Server licenses on Dedicated Hosts and you can do this by running instances with a tenancy of ‘host’. You should not use your own Windows Server license on EC2 instances with a default tenancy unless you have approval from Microsoft to do so. If you have negotiated custom terms with Microsoft and have this permission, please contact AWS support or reach out to your account manager.
Based on this, this is something that should be negotiated with Microsoft first and then work with support or the assigned account manager or TAM.
Microsoft has made some changes to how Windows Server can be licensed inside and outside of a of a customers own data center, depending on the license, when it was acquired and/or renewed, will greatly impact how and where it can be deployed. Dedicated Hosts is usually the best option, VMware Cloud is another option.
AWS Migration evaluator is a great place to get started on determining what licenses are currently in use, and options to migrate to AWS. https://aws.amazon.com/migration-evaluator/
You can also email Microsoft@amazon.com for help with specific licenses questions from an internal expert. The following video was created by one such expert: https://www.youtube.com/watch?v=aOAOEFRh1kg
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