I need to test some encrypting feature inside outlook in an internal network. I'm trying to setup S/MIME encryption for 2 users and exchange some encrypted mails between them.
I generated 2 self-signed certificates (public and private) using makecert.exe
I imported them on both user (different machine, same exchange) respectivly by entering the certificate file path, password and name in the outlook trust center. Outlook process and close the window. I go under security settings and select the certificate.
I also added the certificate under Trust Root/Personal/Trusted Person in windows certificate store.
Now, I'm trying to test this by making a message from user1 to user2 , the window prompt to select a certificate to "sign" the message and it says that there are none available.
Update: I also imported the public certificate of both users in contacts to make encrypting available. Still the same message when I try to send the mail, it says that no certificates can be use to send this message.
UPDATE: The same procedure looks functional in outlook 2007 but does not work in 2010.
What the *!! How come is it so complicated and what i'm doing wrong?