Hello @Jason Steeves
Most likely there is a conflict between the E5 licensing (which will upscale PRO to ENT) and the current license in the Enterprise image. What is the type of key used in the Enterprise image (is it KMS, MAK?)
Can you also verify if SA is active in the machines that are re-imaged with Enterprise? To verify the Windows Enterprise E3 or E5 subscription, go to Settings, select Update & Security, and select Activation.
For more info refer to: https://learn.microsoft.com/en-us/windows/deployment/deploy-enterprise-licenses#step-4-verify-that-enterprise-edition-is-enabled
Regards,
Juan S.