Note: The Screencast about adding a free trusted certificate in SBS 2011 is available here
By default, SBS 2008 uses Self Signed certificates in IIS7. The issuer of these certificates is the CA (Certification Authority) installed on SBS 2008 server, and generally, it is not among the list of trusted root authorities in the remote clients. As a result, the remote clients cannot use Outlook Anywhere, or establish a terminal session to the SBS and workstations on the LAN using the Terminal Services Gateway. In addition, they get the annoying pop-up warning stating that the SSL certificate is not valid.
One way to solve this problem is to distribute and apply the Install Certificate Package to the remote client machines. We have already demonstrated this approach in one of our screencasts (step2).
This could be quite a hassle, and you might not be allowed in certain cases to install software (like the Install Certificate Package) on the client machine.
Considering these obstacles, and the low prices of trusted SSL certificates – as low as $14.99 USD, purchasing and using such a certificate should be the recommended approach.
In the following screencast, we demonstrate how to add a GoDaddy Turbo SSL certificate in Small Business Server 2008.