@James Chan_110, Thanks for posting in Q&A. For windows platform, currently MAM is not available for windows.
https://learn.microsoft.com/en-us/mem/intune/fundamentals/deployment-guide-enrollment-mamwe
For the first picture, when we select "Allow my organization to manage my device", it will register the device into Microsoft Entra. At the same time if automatic enrollment is configured for this user, then the device will also enroll into Intune when it registers to Microsoft Entra.
I notice you mentioned the "Sign in with your work account" keep prompting. It seems there's conditional access for the resource you access is configured. Please let us know how we set conditional access policy.
Meanwhile, please ensure current user is the same one in "Sign in with your work account" picture. And also, please go to Microsoft Entra to check if the device is registered into Microsoft Entra successfully.
Hope the above information can help.
If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment".
Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.