RDP using Azure AD Authentication has stopped working

Question

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/username 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 machines and on the hosted VM machine as well when following the same process to login. We make the connection to the devices just fine, but when we are prompted for credentials, we get a "Credentials that were used to connect did not work, please enter new credentials" error. I have already tried resetting my password, I've modified the RDP file, and all other fixes but it wont seem to resolve. It seems that the AD authentication is failing for some reason, as we have not made any updated to the remote devices.

Any help around this topic would be appreciated,

Thanks.

Answer 1

@Clay Skinner

Thanks for posting your query on Microsoft Q&A.

Based on the information you provided, it seems that the Azure AD authentication is failing for some reason. Here are some possible solutions that might help:

1. Ensure that your network connection is stable and that you can connect to the internet. You can try resetting your router or modem to see if that helps.
2. There are some suggestions shared in this Stack overflow post that you can try: https://superuser.com/questions/1757432/azure-active-directory-users-cannot-log-in-via-windows-remote-desktop-how-to-fi

If none of this works, you will need to create a support request for further assistance. Let me know if you have any difficulties doing that and I can help create a support request for you.
Let me know in the comments if you have further questions. Comment is the fastest way to reach the experts for any questions or help you need.