I have been working with this now a while so i thought that I should sort through the material I found and document it.
First of all, if you do not want to trash your PocketPC device you will need an PocketPC Emulator:
Microsoft® Windows® CE 5.0 Device Emulator
Microsoft Device Emulator 2.0 Beta – Community Technology Preview
Standalone Device Emulator 1.0 with Windows Mobile OS Images
Localized Windows Mobile 5.0 Pocket PC Emulator Images
If you do not have a Verisign (or equal) Cert you need to import the CA cert into the PocketPC Device
Here is a´n article that amongst other thing explains how to do this.