
Explanation:
Box 1: Will not upgrade to Windows 11 Enterprise
Box 2: Will activate as Windows 11 Enterprise
Windows 10 Pro supports the Subscription Activation feature, enabling users to step-up from Windows 10 Pro or Windows 11 Pro to Windows 10 Enterprise or Windows 11 Enterprise, respectively, if they are subscribed to Windows 10/11 Enterprise E3 or E5.
With Windows 10, version 1903 and later, the Subscription Activation feature also supports the ability to step-up from Windows 10 Pro Education or Windows 11 Pro Education to the Enterprise grade editions for educational institutions Windows 10 Education or Windows 11 Education.
Reference:
https://docs.microsoft.com/en-us/windows/deployment/windows-10-subscription-activation