> Ok but waht certificates load in Outlook > I have 3 certificate > cacert.pem > mydomain-key.pem > mydomain-cert.pem
You have one certificate (mydomain-cert.pem), one certificate authority (cacert.pem) and one key (mydomain-cert.pem). What you will want is to add cacert.pem to outlook, so any new certificate validated by cacert.pem is automatically accepted by outlook. You should try something like what is described on the page http://itserv.ait.ac.th/Helpdesk/announce/ie_oe_win.html (sorry for the self advertissement), replacing "AIT CA certificate" with your cacert.pem file. To make a .crt from a .pem, simply edit the file and remove all the text before the -----BEGIN CERTIFICATE----- line. (Can someone confirm?) Bests, olivier