Im trying to work with certificates using outlook and their certificate manager. I got a free one from comodo but it cant be formatted for outlook. Is there a way to get a correctly formatted (free)cert from hotmail or if not any suggestions on what should be done?

I need proof that both sides of the emails are securely encrypted and be able to test out both sides to show the encryption works.
 Im using google apps synce for Microsoft outlook with a gmail account and a proper cert which can encrypt perfectly.

 Also is it possible to sign and encrypt in browser using hotmail? I cant find any buttons or options to do so, Im using Firefox as a browser with current update.

Thanks for the help!!!