RDP to Azure AD Joined Machine: Troubleshooting and Configuration

Troubleshooting RDP connections to Azure AD joined machines can be a challenge, but understanding the basics can help resolve common issues.

The first step in troubleshooting is to check the Azure AD device registration. If the device is not registered, RDP connections will fail.

To troubleshoot RDP connections, start by verifying that the Azure AD joined machine has a valid Azure AD device registration. This is a crucial step, as a valid registration is required for RDP connections to work.

If the device is registered, check the network settings to ensure that the machine is connected to the correct network. A misconfigured network can prevent RDP connections from working.

A valid Azure AD device registration is required for RDP connections to Azure AD joined machines. Without a valid registration, RDP connections will not work.

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You need to turn off Network Level Authentication (NLA) to use Azure AD with RDP. Disabling NLA allows the RDP client to show the Windows login screen where you can enter your login and password.

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RDP works in a way that immediately checks your login and password, which can cause issues when your machine is joined to Azure AD.

To troubleshoot RDP issues, you can try creating an RDP file with the correct settings. The contents of the file should include the IP address of your Azure VM, the prompt for credentials, and the authentication level.

Here are the required settings for the RDP file:

Troubleshooting RDP issues can be complex, but it's essential to ensure the required settings are in place before connecting to your Azure AD-joined VM.

To connect to a remote Azure AD joined machine, you'll first need to ensure the machine is joined to your Azure AD tenant. This involves verifying that the Windows 10 or 11 VM in Azure is properly joined to Azure AD.

To find out if your machine is Azure AD joined, log in to the Azure VM, open Settings, and then select Accounts. Select Access work or school, and if you see "connect to organization Azure AD", it means your machine is joined to Azure AD.

You can also use the local account to sign in to the Azure VM and check if it's Azure AD joined by running the command "net localgroup "Remote Desktop Users" /domain" in the Command Prompt. This will show you the list of users in the Remote Desktop Users group, including those from Azure AD.

To connect to the Azure AD joined machine using RDP, you'll need to create an RDP file with the following contents:

Each line in the RDP file has a specific purpose, such as setting the IP address and port, deciding whether to prompt for credentials, and setting the server authentication level.

Once you've created the RDP file, you can use it to connect to the Azure AD joined machine by entering the username and password in the format "AzureAD\[email protected]".

To successfully RDP to the Azure AD joined machine, you'll also need to add the Azure AD user to the Remote Desktop Users group on the VM. This can be done by running the command "net localgroup "Remote Desktop Users" /add AzureAD\[email protected]" in the Command Prompt as an administrator.

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To RDP to an Azure AD joined machine, you'll need to enable Azure AD login for the Windows VM in Azure. This can be done while creating a new Virtual Machine in Azure, or by using the Azure Cloud Shell experience on an existing Windows VM.

You must configure Azure role assignments for users who are authorized to log in to the VM. The RBAC role assignment of Virtual Machine Administrator Login or Virtual Machine User Login is required when using Azure AD login. You can assign either of these two roles for the users: Virtual Machine Administrator Login, which allows users to log in with administrator privileges, or Virtual Machine User Login, which allows users to log in with regular user privileges.

Here are the two Azure roles used to authorize VM login:

When using the Microsoft RDP client, you need to include the 'AzureAD' prefix to authenticate with an Azure AD user.

The correct format is 'AzureAD\[email protected]', as opposed to '[email protected]', which will result in authentication failure.

You'll also need to use the ".\AzureAD" prefix in a .RDP file, leaving the domain empty.

PKU2U, even when enabled, does not provide Single Sign-On (SSO), so you'll still need to enter your full credentials when connecting.

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Configure RBAC Role Assignment is a crucial step in enabling Azure AD login. You cannot skip this step, as it's essential for logging in to the VM using your Azure AD credentials.

To configure RBAC Role assignments for Azure AD login, you can use either the Azure portal or Azure cloud shell. I prefer to use the Azure portal because it's easy to use.

To add a role assignment, go to Resource Groups and select your resource group, then select Access Control (IAM) and click Add > Add Role Assignment.

On the Add role assignment window, select the Virtual Machine Administrator Login or Virtual Machine User Login role. These two roles are unique and can be assigned to users for logging in to the VM.

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Here are the specific steps to select the role assignment:

You can verify the RBAC role assignments are actually applied by clicking the Role assignments tab in the Azure portal.

The two Azure roles used to authorize VM login are Virtual Machine Administrator Login and Virtual Machine User Login. Users assigned with these roles can log in to an Azure virtual machine with administrator or regular user privileges, respectively.

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This error can occur if you're using the wrong credentials, so make sure you're entering the correct username and password.

To troubleshoot, you can try resetting the password and logging in again.

Also, ensure that the Windows 10 PC you're using to initiate the remote desktop connection is either Azure AD joined or hybrid Azure AD joined.

Note that per-user enabled/Enforced Azure AD Multi-Factor Authentication is not supported for VM Sign-In, which can cause the "Your credentials do not work" error.

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The AADLoginForWindows extension must install successfully for the Azure AD join process to complete. This is a critical step to troubleshoot if you're unable to RDP Azure VM using AAD credentials.

You can check the status of the AADLoginForWindows extension in the Azure portal. Select the Virtual Machine and under Settings, click Extensions.

The status of this extension must be Provisioning succeeded.

If the AADLoginForWindows extension fails to install, you'll need to make a note of the exit code. Here are some common exit codes and their corresponding solutions:

You can refer to the excellent AADLoginForWindows extension troubleshooting guide by Microsoft to resolve deployment issues.