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

Anonymous
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

Windows for business Windows Client for IT Pros User experience Remote desktop services and terminal services
Microsoft Security Microsoft Entra Microsoft Entra ID
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Accepted answer
  1. !Daniel Bradley 1,066 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.

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