Unable to digitally sign or encrypt messages in Mail

I recently switched from a PC to a Mac and I have been unable to digitally sign or encrypt any of my e-mails. I'm currently running version 3.3 (926.1/926) for Mail and I made sure that my .cer security certificate is located in Keychain Access as well as certificates for my contacts. My certificate is valid because it has the green checkmark next to it.
I know what the *digitally sign* and encryption buttons should look like and where they should be located when composing e-mails, but they are just not there for me. Does anyone have any advice on how to fix this. Does it matter which folder the .cer security certificates should be located in for Keychain Access? Or is there a specific option I need to enable within Mail to be able to see those buttons?
I know that Mail is recognizing security certificates for e-mails that are being sent to me because it is showing the starburst/checkmark icon next to those e-mail addresses, and my Address Book is showing that same icon next to those e-mail addresses for my contacts.

I finally have a solution to this problem. I had been trying to use a .cer security certificate issued by Comodo, it had worked just fine on Windows but my Mac didn't seem to like it. I also tried creating my own certificate through OSX, but even after I created it I still couldn't see the buttons.
I had someone direct me to this webpage which ultimately helped me fix the problem:
http://allforces.com/2007/03/02/email-security/
I ended up using Thawte to issue me another security certificate (this time it was an x.509 file), the security certificate automatically opened in Keychain Access and downloaded to the Certificates and My Certificates folder. Once I shutdown Mail and restarted it I had the buttons for both encryption and digitally signed. Of course the encryption button is still greyed out because it is a new certificate and I need to make sure my Address Book contacts have a copy of it before I can encrypt.
Message was edited by: Matthew Little

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