Share via

Remote Desktop Gateway with Azure 2FA asking two times for password

Danny M 51 Reputation points
2022-02-16T08:09:13.12+00:00

Hello everybody,

I have set up a Windows Server 2016 Remote Desktop Gateway with a NPS Server and was able to connect everything to Azure AD.
2FA works fine, but for some reason, the user needs to type in the password two times (Before AND After the 2FA Challenge).

Has anybody encountered this before?
Hints where to look would be very appreciated.

Thank You!.

DM

Remote Desktop
Remote Desktop
A Microsoft app that connects remotely to computers and to virtual apps and desktops.
4,506 questions
Microsoft Entra ID
Microsoft Entra ID
A Microsoft Entra identity service that provides identity management and access control capabilities. Replaces Azure Active Directory.
21,410 questions
0 comments
Accepted answer
  1. !Daniel Bradley 1,056 Reputation points MVP
    2022-02-16T12:22:35.383+00:00

    What is the exact process the user is taking?

    Are they logging into RDweb and then opening Desktop collection, or do they just have an RDP client link on their desktop?

    It sounds like they are opening the RDP client link on their desktop, accepting MFA for connection to Remote Desktop Gateway and then having to login to the Remote Desktop Server. This can be solved by ticking the box: Use my RD Gateway credentials for the remote computer under advanced settings in the RDP client.

0 additional answers

Sort by: Most helpful
Most helpful Newest Oldest

Your answer

Answers can be marked as Accepted Answers by the question author, which helps users to know the answer solved the author's problem.