Unable to login with Entra ID in Azure AD joined VM Windows Server

Question

Unable to login with Entra ID into Azure AD joined VM Windows Server.

Below is the sequence of activities done.

1. Created an account in Microsoft Office 365
2. Successfully added an existing Domain, with all the instructions of MX Record etc.
3. Entered into Azure portal with same credentials and Successfully created subscription, VM Windows 2022 Azure Data Center
4. Successfully able to login into VM with local admin credentials.
5. DHCP and DNS are automatically set to 168.63.129.16
6. AzureAD = Yes.
7. Created two users in Office 365 admin center and could see them in Entra ID and added to a newly created Group.
8. Gave Azure role assignment the above user Group for "Virtual Machine User Login" role.
9. Trying to login to VM through RDP with the above user. Login Attempt Failed error message displaying. Also, it displays that the remote machine is AAD Joined. If you are signing in to your work account, try using your work email address.
10. Tried giving work email ID. Same error appears. Login Attempt Failed.
11. As per another blog went to Microsoft Entra Admin Center>>OverView>>Properties>>Manage Network Defaults and disabled security defaults. Still same error. Please help:
    1. Login to VM with Entra Ids (Office 365 IDs)
    2. How to join this VM to custom domain, which was added through Microsoft 365 admin center. I do not want to have onmicrosoft.com. So added a domain successfully to Entra. Currently VM is in workgroup. The DNS IP shows 168.63.129.16.
    Thanks and Regards, Ram

Answer 1

@Rama Prasad

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.

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