SBS 2008: Receiving Certificate Errors when connecting to Clients/Servers with TS Gateway or Remote Web Workplace
Remote Desktop Disconnected: You may receive the following errors when attempting to access a client machine through the Remote Web Workplace (RWW) or the TS Gateway:
[To connect to Remote Web Workplace, you must install the proper certificate. Contact the person who provides technical support for your network.]
Likewise, connections to TS Gateway will fail as well. You will receive the following error:
[This computer can't connect to the remote computer because the certificate authority that generated the Terminal Services Gateway server's certificate is not valid. Contact your network administrator for assistance.]
To determine whether you trust the certificate or not, browse to RWW from Internet Explorer. If it’s not trusted, you will receive the following error in IE[…]

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