RD Gateway Issues with Windows Server 2012

I am having issues relating to my RD Gateway server when attempting to connect from outside of my local network.

My RD environment consists of a single server (RDSH, RD Gateway, etc.), Windows 8/8.1 clients, and Mac/iOS clients using Microsoft's Remote Desktop app.

I previously had issues connecting via the RDWeb Access and RemoteApp and Desktop Connections, but those problems seem to be resolved (no changes were made to fix the problems and I will have to perform further testing to be sure these issues no longer exist).

Using Microsoft's new Remote Desktop app (via iOS or OS X), it will populate the remote resources but when I try to connect to a program, I get the error "The gateway failed to connect with the message: 404 Not Found"

The only thing I can imagine that would be causing these issues would be the RD Gateway or possibly an IIS setting. Again, all three of these methods work just fine internally (which I assume is because it is ignoring the RD Gateway).
steven_theckAsked:
Who is Participating?
 
Cláudio RodriguesFounder and CEOCommented:
What is the FQDN for the deployment?
Normally we set it all to external FQDNs using this:

Change published FQDN for Server 2012 or 2012 R2 RDS Deployment
 
http://gallery.technet.microsoft.com/Change-published-FQDN-for-2a029b80

Cláudio Rodrigues
Citrix CTP
Microsoft MVP - RDS
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Gareth GudgerCommented:
Do you have a third-party certificate installed on the RDS Gateway?

Are you using an external name in the RDS Gateway?

Did you configure the RDS Gateway address in the RDP client?
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steven_theckAuthor Commented:
I have a wildcard certificate from GoDaddy and it is setup in the RD Gateway Manager, IIS, and the RDS settings in Server Manager.

I am using an external name in the RDS Gateway (remote.mydomain.com) and the internal name is internal-rds.corp.mydomain.com.

I did try configuring the gateway in the Remote Desktop app, but the issue persists.
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Making Bulk Changes to Active Directory

Watch this video to see how easy it is to make mass changes to Active Directory from an external text file without using complicated scripts.

 
steven_theckAuthor Commented:
My apologies for the delayed response, but I have been extremely busy over the holidays.

@ tsmvp, I downloaded and ran the script from the TechNet page you provided and that allowed me to connect! Thank you so much for your assistance!
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DieselTechCommented:
I cant connect outside to my  RDS Gateway 2012.

please help
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steven_theckAuthor Commented:
@DieselTech If you would like assistance from the experts, I would recommend creating a new topic. Experts receive points for successfully answering questions, and many pay for their Experts Exchange memberships this way.

You will also need to provide more information other than you cannot connect. Saying that you cannot connect from outside your organization could be changing the published FQDN (as was the solution for my case), obtaining a third-party SSL, your firewall blocking incoming connections, incorrect DNS settings (locally or through the provider of your static IPs)... The list goes on...
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