Getting prompted to login again when clicking on the app

asked 2020-08-31T20:12:34.097+00:00
SenhorDolas 986 Reputation points

I setup RDS on a W2K19 server - one server Session Host and one server with all the other roles.
I can login fine internally but when using it externally I get prompted to login again when I launch the app.
I am fronting the web interface with Azure App Proxy.
Any ideas?

Azure Active Directory
Azure Active Directory
An Azure enterprise identity service that provides single sign-on and multi-factor authentication.
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Remote Desktop
Remote Desktop
A Microsoft app that connects remotely to computers and to virtual apps and desktops.
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Accepted answer
  1. answered 2020-09-01T02:18:19.777+00:00
    Jenny Yan-MSFT 9,196 Reputation points

    1.Kindly check if you have enabled "Bypass RD Gateway server for local address". It will omit the RD gateway when remoting form internal.

    2.Kindly check if you have enabled single sign-on between RD Web and RD Gateway with command shared in step 8.

    If everything configured well, the users are asked to authenticate once to Azure AD and once to RD Web, but they have single sign-on to RD Gateway.

    -----Please "Accept as answer" if the reply is helpful-----

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