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

Step 1 In this step, we take a look at the Self-Issued SSL Certificate used in Small Business Server 2008, and the Certificate Distribution Package.

Step 2 In step2, we import the SBS 2008 Self-Issued SSL Certificate on the mobile device, and configure ActiveSync to connect to Exchange Server 2007.