With Small Business Server 2008, you have the option to use a third party SSL certificate or the default self-signed SSL certificate. By default the self-signed certificate is valid for two years, but how to you renew it without interrupting OWA, Outlook, and Exchange? When the certificate is expired, Outlook 2007/2010 will give you an error message when opening, that the certificate is not valid. Here are the steps to fix it.

1. Goto the Windows SBS Console, click on Network Tab, then Connectivity Tab
2. Click on the certificate icon, then click the “view certificate properties” in the right pane. In the General tab of the new window, it will show the dates that the self-signed certificate is valid for.
3. In the “Connectivity Tasks” area, click “setup your Internet address”, go through the wizard to renew your self-signed SSL certificate.
4. When you now check the certififcate properties, you will see that it is now valid for another two more years.

Thawte now is conforming to the new 2048 bit standard for their SSL certificates, which will require you to install two intermediate certificates on your server before they work and is validated. Below are the links to the articles and intermediate certificates. Download both certificates and import them into the “Intermediate Certificate Authority” in the Certificates MMC.

Thawte Intermediate and Cross Root CAs - link

Primary and Secondary Intermediate CAs - link