Remote Desktop Connection Fail from Windows 10 Using Azure AD Credentials

Remote Desktop Connection Fail from Windows 10 Using Azure AD Credentials

Just over a week ago I repaved my Surface Pro 3 to a clean install of Windows 10 build 10074 (since then I’ve upgraded to 10122) and since we don’t run our own domain at Built to Roam I figured I would sign into Windows 10 using my Office 365 credentials (ie my Azure Active Directory credentials). For the most part this seems to be relatively stable except for a couple of scenarios:

Firstly, after the upgrade to 10122 it looked like it had completely junked my user profile as I couldn’t sign in using either my PIN or Password. The error was actually a little cryptic as it was complaining it couldn’t reach a login server. In the end I rebooted and I was able to sign in fine.

The second, and slightly more annoying thing is that the AzureAD credentials seem to be causing some issues with authentication in a couple of places.

–  The first is with Remote Desktop into a cloud service running in Azure. Normally I would only have to specify my username (eg “admin”) and my password and it would authenticate without any issues. However, now I get the following error dialog

Remotefail

Remote Desktop Connection
An authentication error has occurred (Code: 0x80004005).
Remote computer: xxxxxxx.cloudapp.net

 In the end I prefix my username with “local” (eg localadmin) and it worked fine.

–  The second occurence is trying to connect to a network resource. This network resource is actually a NAS but for the life of me I can’t work out what domain prefix to give it. It somehow tries to resolve my AzureAD credentials and then is failing. Very frustrating as I now have to retrieve the data off my NAS using a different computer.