RemoteApp and Desktop Connection - Default Connection URL - Windows Server 2012 R2

Question

Hi,
I'm building an Remote Desktop envoirement for our organisation wich includes the following servers:
2 Domain controllers with Remote Desktop Gateway, Licensing and Broker (1 broker functional, no HA, still in progress of building), RDWeb installed.
2 Remote Desktop Host Servers for the user logins (no applications just the desktop).
2 Remote Desktop Application Servers (RemoteApp) with all of our applications installed.
2 File Servers using DFS replication.
All of those servers are Windows 2012 r2.
Our purpose is to deploy RemoteApp's to the Remote Desktop Host servers using the GPO Default Connection URL.
The problem is that it won't apply to the users who log on to the Remote Desktop Host servers. I'm struggling with this issue for a while now and tried different possible solutions. Such as the delegation credential GPO, making the users local admin, making
the users domain admin etc etc.
My guess is that the GPO hangs on the fact that when i try to manually run the wizard to connect to the RemoteApp and Desktop connections, my credentials are asked. Which i think is odd because i'm already logged in as an domain user. I'm having the exact same
problem with the domain administrator account.
When i'm connecting manually by entering the credentials in the connection wizard everything is working as it should, it just won't connect automatically
Does someone has an solution for this?
Kind Regards,
Geoffrey van Meurs

Answer 1

so am I correct to assume that your issue is really with RemoteApps single sign-on (SSO)?
You have users which RDP to RDSH and again you're attempting to publish RemoteApps in that same environment?
I haven't done SSO but there is a lot of info about it on the web:
http://social.technet.microsoft.com/Forums/windowsserver/en-US/ed4447b5-2958-404b-883c-9aefa038ad61/single-sign-on-remoteapp-and-desktop-connection?forum=winserverTS
Secondly, you may need to look at your GPO loopback settings to ensure the policies are being properly applied.  Use RSOP as well.  Try using a local GPO to see if it makes a difference with a non-admin test user.  Check event logs for GPO
processing errors/conflicts.  Use gpresults, etc.
Something else worth noting here is that RemoteApp publishing is really not meant to be done inside RDSH, it's usually done on the user's workstation, therefore eliminating the need for them to even login to RDSH, reducing the number of hops and complexity. 
For what you're doing, you're better off using RDWeb to publish the applications to them or using the old school method of just having app. shortcuts on the Desktop/Start menu in RDSH since they're already getting a published desktop anyway.  Or just
use RemoteApps on their workstations via GPO.  Just some thought if I'm understanding your goals here, but it sounds like you would need to read up on RemoteApp SSO.