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Terminal Services Gateway problem with self-created certificate

Posted on 2010-09-03
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Last Modified: 2012-06-27
The set is like that:

Server 2008 R2 Enterprise has 4 virtual servers installed:
1. Testing server
2. Engineering server
3. Domain Controller (not yet created)
4. TS Gateway
In a testing environment all worked well. TS Gateway had self-signed certificate and a copy of it was installed on client PCs. Connection was flawless.

On the day host server moved into client's domain environment all was good, too:
1. All servers were assigned proper IP addresses to fit present network.
2. Domain controller role was installed and added to present domain.
3. All servers including host and guests were added to domain.

After that the test connection via TS Gateway was done with external access to TS Gateway (dyndns.org name created and port 443 forwarded to TS Gateway server on the main router). All works as it should. But as soon as I try to connect from external client there comes a delay, then remote connection client window freezes and an error message pops up saying:

"Your computer can't connect to the remote computer because the Remote Desktop Gateway server's certificate has expired or has been revoked. Contact your network administrator for assistance"

External client used has windows 7 Ultimate. Before servers were moved into domain, connection from the same client but different certificate (to fit testing office's dyndns.org name) was used successfully.

The only changes that occurred  on TS Gateway server are:
1. Changed for new self-created sertificate to match dyndns name.
2. Deleted server's certificate (created initially for server itself), but leaving newly created certificate only.

Just to mention - it doesn't matter the self-created certificate for now - we install it's copy in the root certificate authority folder on client's PC and it proved to work ok as a temporary solution.
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Question by:sycamoresrv
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by:evilsi
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Hi,

From what you have described the issue lies with the deletion of the old certificate. It would appear your new certificate doesnt have the components that your original certificate did. Did you create the new cert from the same template as the original one? Try requesting the TS gateway certificate again using the http://servername/certsrv and installing it.

hope this helps

Si.
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by:sycamoresrv
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Yes, I deleted all certificates to make sure I don't mess with the old ones and create a new one right from the management menu of TS Gateway.
I went even further - reinstalled the whole virtual TS Gateway server from scratch to make sure everything to be intact there but same result.
What I want to stress is that I am capable to connect using Gateway's dynamic name from any PC connected internally (even so I unchecked the option to avoid Gateway for local addresses). I have a strong suspicion my RV042 router does not pass through on port 443, although the port range forwarding rule is implemented.
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by:evilsi
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you seem to have covered the bases for the TS gateway then.. Does that router have to capability to have remote management or SSL VPN services (like Draytek routers).. If so you may have to disable those router services..

Si.
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by:sycamoresrv
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no, i checked many times - there are no settings for VPN services being active on it. Thinking of swapping it with some other working model for tests.
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by:evilsi
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Can you rdp to the server from outside as a test with port forwarding of 3389?
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sycamoresrv earned 0 total points
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Yes, in fact rdp port forwarding works fine but port 443 does not. I searched through internet on RV042 problems and found many references concerning problems with SSL port forwarding, even if you have the latest firmware.
I installed another working router that was tested in the office here and it proved to blame RV042 as there are no problems with connection for TS Gateway anymore.
Thank you evilsi for advises.
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