Windows Server and SQL Server Enterprise licenses issue when failover with AWS DRS

DRS will replicate the entire disks including all OS/Application settings.

Depending on the version of Windows/SQL and how they have been licensed they will continue to use that license. eg licensing is done via volume licensing/KMS when the server is started in AWS the server will attempt to contact the KMS server to check/get a license. There is some grace period if it cannot contact KMS before the server becomes unlicensed

I cannot give any licensing compliance advice and will depend if you have software assurance or not

DRS will replicate entire disks over, which will include any license configured in your OS

You have the option when setting up DRS Launch settings, to re-configure Microsoft licensing. This conforms to Microsoft Licensing on AWS

See https://docs.aws.amazon.com/images/drs/latest/userguide/images/default-drs-launch-settings-wizard.png

Source: https://docs.aws.amazon.com/drs/latest/userguide/quick-start-guide-gs.html#configuring-target-gs