Hello,
A coworker has a CaC with a certificate on it. We got it imported into the Outlook trust center and everything looks good there. He is able to toggle "Signed" and send a test message to himself with no issue, however if he toggles "Encrypt" he gets:
"Microsoft Outlook had problems encrypting this message because the following recipients had missing or invalid certificates, or conflicting or unsupported encryption capabilities:"
I tried getting my own cert and sending signed emails between two email accounts to check if doing that allows sending of encrypted email....and I get the same message. I was using the same cert on both accounts though so I'm not sure if that's part of it.
The person my coworker is trying to encrypt messages to does not want to be bothered so I don't want to have him try sending a signed message first in the hopes that it allows encryption later without knowing for sure.
Any assistance? It's on Outlook 2013 on Office 365.