Windows 10: RDP with Azure AD Auth has stopped working.

Our organization has a couple Windows devices located at a colocation data center. Since we began as a company, we have used RDP to remote into these device for operations and troubleshooting. They are configured to allow RDP for specific users with Azure AD Authentication. One of the machines hosts a VM, which we also have configured to allow RDP with AAD auth. So we would spin up RDP, add the IP of the given device, and use the AzureAD/*** Email address is removed for privacy *** as the username format. Last week, this still worked fine as usual. But today all users are getting a login failed error on both of these

:)

 

RDP to Azure AD joined computer

Hi Vijay,

Thank you. For those interested, I also posted the question on the Windows IT Pro forum and the Windows Server RDS forum:

RDP to Azure AD joined computer

RDP to Azure AD joined computer

 

RDP to Azure AD joined computer

I am trying to connect to a remote computer that is Azure AD joined. Both the client and host computer are running Windows 10 version 1809. Currently I am connecting without NLA to be able to authentication myself, but I would like to connect with NLA.

According to this article: Connect to remote Microsoft Entra joint this should be possible, providing you use the username format "AzureAD\JeroenDeWit" to connect. However, this results in the following error:





Other guides like https://cloudbuilder.io/documentation/Windows10Pro-RDP-AzureADJoined/ also suggest authenticating without NLA.

Am I doing something wrong or is Microsoft doing something wrong?

 

How to connect to Azure-hosted DB with Windows Auth on local workstation

Hello,

This is something we have wanted to implement for some time now, but it always falls to the wayside because higher priority tasks come up and SQL Auth works. We have several Azure VM's running, some dataservers and some webservers.

From our workstations we are only able to connect to our databases using SQL authentication, which is not ideal.

However, we can RDP to the SQL servers and from there use Windows Authentication with SSMS to log in successfully. Convenience and workflow are the reasons why we wouldn't want to do that, as well as the latency going through RDP introduces (it just feels
slightly off).

We want to stop using SQL authentication because it just adds another headache to our work; Another password to remember, as well as being less secure.

We are using a VPN, which I guess tunnels to Azure but I'm not sure why we cannot authenticate with our windows credentials. How can we achieve this?

Thanks