Remote Desktop Gateway connection intermittent with certificate error
Posted on 2014-12-16
When attempting to remote desktop into an RDS gateway server, we are receiving the following error:
"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can't connect to the remote computer because the Remote Desktop Gateway server's certificate has expired or has been revoked.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."
The server is Windows Server 2008 R2, and we are positive the SSL certificate is valid. RDWeb is working fine and can be used to remote desktop other computers on the network without issue.
We have already tried reinstalling the RDS role and had the certificate reissued. We have been seeing this issue connecting from Windows 7, Server 2008, and from the Microsoft Remote Desktop app from iTunes. Oddly enough, if you keep trying, the connection will eventually succeed after a random number of times. On some systems, the connection succeeds nearly 100% of the time.