In Accounts>Advanced>Security>

I am able to select my certificate to digitally sign email but on the same screen i cannot select the same certificate under the 'Encryption' heading. The 'Choose A Certificate' dropdown is greyed out. Additionally On Certificate Authentication option - i see only two com.apple.idms.... certificates but not mine. 

I've copied my certificate into Microsoft_Entity_Certificates and Microsoft_Intermediate_Certificates in keychain - but this has had no effect. 

I can however work fine in Apple Mail - sending digitally signed and encrypted emails without any problem.
I have really run out of ideas here.  All that I am trying to do is add certificates to contacts that I have in my address book.  When I go to the "Details" tab in an email and try to "Add Encryption Certificate to Contacts" it never shows up on the contact.  When I download the certificate manually then go to the contact hit the "+" button and try to add it, it seems like it is adding it but never shows up.

So far I have done a "rebuild" on the identity, created a new identity and tried every which way to add the certificates.  They just will not add...  If anyone could help me out with this issue I would very much appreciate it!