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troubleshooting Question

Certificate issues with RemoteApp and the internet

Avatar of plymouthmuscle
plymouthmuscleFlag for United States of America asked on
Microsoft IIS Web ServerRemote AccessWindows Server 2008
4 Comments1 Solution1998 ViewsLast Modified:
I'm trying to set up RemoteApp with Server 2008 and terminal services.
I want employees to be able to access an internal application from the outside.

So far I think I seem to be doing pretty well, but I've hit a snag I can't seem to get past. I've gotten the TS website ported through the router and can access it successfully from the outside. I've also gotten the TS website SSL'd up and that seems to be working fine.
My problem is when I click on the application I want to launch inside the TS website it gives me the usual logins, and then throws a certificate error.

"The remote computer could not be authenticated due to problems with its security certicate. It may be unsafe to proceed"
"The certificate is not from a trusted certifying authority"

I have two options. One to view the certificate and the other to click "OK"
When I click "OK" the error screen goes away but nothing happens.
Installing the certificate on the remote machine did not change the error.

How do I move past this error? Can I somehow self sign my certificate in order for it to work. I would prefer not to purchase anything.

Thanks for any advice.
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