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Certificate error when connecting to RemoteApp outside of private network

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I have a server running Windows Server 2012 R2. It is configured as an all-in-one RDS server - all roles are installed on it. We've configured it primarily to use an application as a RemoteApp - the application is hosted at a different site, and this RDS server is at that site. We have a site to site VPN set up, so that it is all a part of our domain. The issue I'm having seems related to the fact that our internal network is .local, but the certificate only has a single .com name, so that we can access it from the Internet.

Everything works, though what I'm trying to clear up is a certificate error. When connecting to the RemoteApp from outside of our private network, we get the error "The server name on the certificate is incorrect." This occurs after entering credentials.  The public name of the server (rds.contoso.com) is different from the private name (server.contoso.local).  We can proceed through the error and connect (though we'd like to fix it).

I implemented a fix that I found elsewhere to try to fix this.  This was to add a custom RDP setting like so:

Set-RDSessionCollectionConfiguration –CollectionName QuickSessionCollection -CustomRdpProperty "use redirection server name:i:1`nalternate full address:s:rds.contoso.com"

That seemed to make some progress, then we got another error.  I made a change to the RD RAP in RD Gateway Manager - by default, it allowed access to Domain Computers (which rds.contoso.com did not exist as a domain computer). I modified it to allow access to the rds.contoso.com name.

I now receive a different error message and that's where I'm stuck.  The heading on the message is RemoteApp Disconnected.  The text of the error is 'Remote Desktop can't find the computer "rds.contoso.com".  This might mean that"rds.contoso.com" does not belong to the specified network.  Verify the computer name and domain that you are trying to connect to.'

Any thoughts on what I can do next?  When I roll back the changes I've made, I'm again able to connect fine, I just have the certificate error again.


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