That is a really odd issue.
I wonder if the RD App works anything like MSRA /offerra
So a weird problem I have with my users is this. We use a Cisco ASA 5500, we 
all work from home.
I personally since I am administrator have a Cisco Pix 515e at my house which I 
establish VPN Tunnels to my Colo facilty  which houses our servers and the ASA 
5500
The other remote users use Shrew client to establish VPN Connections to the ASA 
5500

Now if I do an MSRA /offerra to try and shadow them and help with them 
remotely, then it will fail to connect.
What I had to wind up doing was edit their local hosts file with entries for 
our domain as well as one of our PDC servers.
for example
10.78.0.6             domain.com
10.78.0.6             PDC.domain.com
Once I put that in, I am now able to offer remote assistance to them and can 
connect…..it seems the issue was the workstation I would connect to, didn’t 
know how to authenticate my credentials, even though they were on VPN and the 
VPN config is built to use our internal DNS servers….but it is also split 
tunneled, so not all traffic would route back through the ASA

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