One of the problems which you might have encountered when using Self-Issued SSL certificate is configuring ActiveSync on Mobile Devices to connect to Exchange server.

If you do not use Small Business Server 2008 and you are looking for a Step-by-Step video tutorial about “How to export a digital certificate”, check this Screencast - “How to Export Self-Issued (Exchange 2007) Certificate to a File, and Install it on a Mobile Device”

A default installation of Small Business Server 2008 uses a Self-Issued SSL certificate for the Exchange Server 2007 installation. We have already demonstrated in one of our SBS 2008 Screencasts how to import the Self-Issued certificate to a client machine and allow normal functionality of Remote Web Workplace.
You have to follow a similar approach before you are able to configure ActiveSync, and connect your mobile device to an Exchange Server which uses Self-Issued SSL certificate.

In the following screencast, we will show you Step-by-Step how to import Self-Issued SSL certificate in a mobile device. We will also demonstrate how to configure ActiveSync and connect the mobile device to an Exchange Server 2007