Azure Active Directory (AAD) Joined Server Remote Access Guide

Overview:

This will be a three-part series covering the following topics:

1. Microsoft Server 2022 Azure VM In-Place Upgrade Automation

2. Managed Identities - AAD Login for Windows Server Extension & Access Control

3. Azure Active Directory (AAD) Joined Server Remote Access Guide

AAD Joined Server Remote Access Guide

Part 3: AAD Joined Server Remote Access Guide

Now that our server is AAD Login enabled, we can attempt RDP access. This must be performed on an Azure AD Joined machine. If you are using an Azure AD Registered machine, use the following format for login: AzureAD\[email protected]

1. Connect to your VPN if your remote server does not have a Public IP

2. Open Remote Desktop Connection (MSTSC)

3. For Computer type in the internal or Public IP of your server

4. You can leave the User name blank or type in your standard UPN, e.g., [email protected]

5. Hit Connect

6. You will be prompted for your authentication method. Using a standard password login WILL NOT WORK. You will receive The logon attempt failed.

7. You must use Windows Hello - Face, Fingerprint, or PIN!

Windows Hello Authentication for Azure AAD Login

8. Enter your chosen authentication method and select OK

Additional Troubleshooting Information

You can reference the following article for more extensive connection troubleshooting steps:

Login to Windows virtual machine in Azure using Azure Active Directory authentication

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You can now remotely access an Azure server using the AAD login preview attached to a workgroup.

Feel free to comment below with any questions or comments.

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