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RemoteApp can't connect externally through RD Gateway

Posted on 2013-11-11
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I recently set up Remote Desktop Services on Server 2012.  Everything is working except connecting RemoteApp externally (through RD Gateway).  When connecting to RemoteApp, I get the following error:

RemoteApp Disconnected - Your computer can't connect to the remote computer because an error occurred on the remote computer that you want to connect to. Contact your network administrator for assistance.

I have researched this error and can't seem to figure it out.  I'm using a self-issued certificate.  I've installed the certificates on the client machine and I can connect via Remote Desktop externally without any certificate warnings. If I uncheck "Bypass RD Gateway server for local addresses" then I also see the same error internally. So it must be a configuration or certificate issue in RD Gateway?  We plan to purchase a public certificate, but I wanted to see this all working first.   Would a public cert resolve the issue?  Any suggestions? This is a very basic installation of RDS.  All Remote Desktop roles (except Licensing) are installed a single machine.  Can I use RD Web Access & remoteApp without RD Gateway as we used to do in Server 2008?
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Question by:robinsonbud
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by:Ryan Mangan
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The issue you are seeing is because you are using self assigned certificates.

you can test this by disabling certificate authentication for test purposes:

use the following PowerShell Cmdlets to do this:

Set-RDSessionCollectionConfiguration –CollectionName QuickSessionCollection -CustomRdpProperty “authentication level:i:0”

Once you are finished testing use the following cmdlets to reset this:

Set-RDSessionCollectionConfiguration –CollectionName QuickSessionCollection -CustomRdpProperty “"

Have a look at the following article: http://ryanmangansitblog.com/2013/03/10/configuring-rds-2012-certificates-and-sso/

Best regards,

Ryan
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robinsonbud earned 0 total points
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I resolved this a long time ago.  The problem is that RDP client 8.0 doesn't work properly with the Remote Desktop gateway.  The solution is to remove RDP client 8.0, reverting to the previous version.  The way to do that is to remove it in Windows Updates.  You need to remove KB2592687.  So if you remove this update, then you will revert back to the previous version, and, voila, RDP now connects without the above error!  This was some time ago, so I'm not sure if Microsoft has fixed this issue or if there's now a better solution.  Anyone care to update this?  I'll see if I can get a response from Microsoft.
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