Thank you for posting your query on Microsoft Q&A, from above description I could understand that you have Entra ID joined a Windows server VM and are getting error while trying to login with worker school account.
Please do correct me if this is not the case by responding in the comments section.
As per Microsoft Entra joined devices documentation server join is not entirely supported nor a recommended way.
- However if your VM is hosted on Azure then the recommended way would be to use Entra ID extension.
***Please "Accept the answer (Yes)" and "share your feedback ". This will help us and others in the community as well.
Thanks,
Akshay Kaushik