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Remote Desktop Gateway and WebAccess Deployment - Multiple Logon Prompts

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I'm having a few issues with some multiple logon prompts using "Connect to a remote PC" via RD Web Access.

I am able to log onto the RDWeb without a problem.

Essentially once I make a connection to my end-device I first receive a logon prompt, I'm authenticated, then I'm asked again for another logon prompt. Any ideas how to resolve this?

My layout is simple:

1 VM in the DMZ that has the Remote Desktop Gateway and Remote Desktop Web Access roles installed. No connection broker, or session host.

With my deployment I have a wildcard certificate bound to the Remote Desktop Gateway and it is bound properly in IIS. Remote Desktop functionality through the RDGateway works just fine. However, the only nuisance is that I get prompted multiple times for credentials when accessing the end-device regardless if my connection is from a domain-joined machine or a non-domain joined machine.

I've tried using Web Single Sign On via http://anandthearchitect.com/2014/01/20/rds-2012-r2single-sign-on-using-windows-authentication-for-rdweb-page/ and it still does not work.

Any ideas?

Thanks,

Dan



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