Microsoft RDWeb and RDG

I just labed my use case out and it worked just as expected. An RDP profile with a server type of remote desktop web access which connects directly to my RDG/RDWeb server. The only issue I ran into was that the host name requested must be the same as what is in the certificate. Once I changed that, everything worked like a champ. Will test with the customer and provide feedback.

Still not working in the customer environment. Trying to understand the differences between RDWeb, RDG and RD Session Host. Below is what I have so far from using Google. From what I understand at this point is that RDWeb is a portal and nothing more, RDG is performing the same function as the BIG-IP to allow 443 versus 3389 and the RD Session Host simply hosts applications users will access.

Remote Desktop Session Host (RDSH) is a role in Remote Desktop Services (RDS), which was known as or Terminal Services prior to Windows Server 2008 R2. RDSH servers host Windows applications or desktops that are accessed by remote users over a network connection.

The RD Gateway server uses port 443 (HTTPS), which provides a secure connection using a Secure Sockets Layer (SSL) tunnel. A Remote Desktop Gateway Provides The following Benefits: Enables Remote Desktop Connections to a corporate network without having to set up a virtual private network (VPN).

Microsoft Remote Desktop Web Access (Microsoft RD Web Access) is a Remote Desktop Services role in Windows Server 2008 R2 and Windows Server 2012 that allows users to access RemoteApp and Desktop Connection through the Start menu or a Web browser.

Note: When implementing Connection Authorization Policies the RD gateway server provides an error stating you are not authorized. When implementing Resource Authorization Policies, only the generic RDP unable to connect is presented to the user. Not sure if this is the issue I am running into on the customers network but if we get that far it should make troubleshooting much easier.

Well, even with a performance layer 4 in place I get nothing. RDP session just sits there Initiating Remote Connection and then ends with Remote Desktop can't connect to the remote computer for one of these reasons.....

When successfully connecting, within the TerminalServices-Gateway log within Windows I see The user "steve.lyons@demo.lab", on client computer "10.1.20.29:52846", has initiated an outbound connection. This connection may not be authenticated yet.

Then immediately after I see The user "demo\steve.lyons", on client computer "10.1.20.29", met connection authorization policy requirements and was therefore authorized to access the RD Gateway server. The authentication method used was: "NTLM" and connection protocol used: "HTTP".

During unsuccessful attempts I only see The user "steve.lyons@demo.lab", on client computer "10.1.20.29:52846", has initiated an outbound connection. This connection may not be authenticated yet.

Here's a document that explains Remote Desktop Services roles.

Thanks for the comment rob_carr. Unfortunately, this wasn't documented so well. The cause of my issue was due to non-browser user agents which were being requested for authentication by APM. Since I can define known IP's I was able to disable access for these user agents using the following iRule.

when HTTP_REQUEST {
    if { [string tolower [HTTP::header "User-Agent"]] == "ms-rdgateway/1.0" || [string tolower [HTTP::header "User-Agent"]] == "kerberos/1.0" } {
            HTTP::header insert "clientless-mode" 1
            ACCESS::disable
    }
    else {
        ACCESS::enable
    }
}