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RD Gateway and Web Application Proxy and AD FS

ng flag

I am trying to deploy an RD Gateway in combination with WAP (Web Application Proxy) and AD FS pre-authentication as described here.

For a "proof of concept", I've decided to deploy all RDS roles to one server. Simplified, my environment now looks something like this:

setup overview

Where the server labeled "RDS" contains these roles:

  • RD Web Access
  • RD Gateway
  • RD Licensing
  • RD Connection Broker
  • RD Virtualization Host

On the AD FS Farm, I configured the following Relying Part Trust, which only has the identifier set:

relying party trust

And on the WAP, the published application looks like this:

wap application configuration

Now, Internally everything works. A client in DEVPROD can access RD Web and connect to the vdi resources.
On the WAP, everything works. On any server of the farm, I can access RD Web and connect to the vdi resources.
From outside, I can access RD Web, but connections to the RD Gateway fail with this error message:
error message
On some clients, I also get:

Your computer can't connect to the remote computer because the Remote Desktop Gateway server is temporarily unavailable.

What I've tried/checked

  • All certs used are trusted and rdweb uses the correct one
  • IIS does not have unused bindings
  • Using windows authentication for IIS
  • Setting pre-authentication to required in the custom rdp properties of the collection
  • Setting DefaultTSGateway and radcmserver in the IIS application settings

Where would you start diagnosing this issue?

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