So, I’m attempting to learn how to send encrypted email using Windows Live Mail (or Outlook). I’ve got the basics in place: self-signed root certificate with which I’ve signed my email certificate.
Problem is the encryption doesn’t work consistently. Sometimes the recipient will be able to read the encrypted message and sometimes he won’t.
I’ve discovered that if I can read the copy of my encrypted message saved in my Sent folder, then my recipient will not be able to read it. And if I cannot read my Sent copy, then my recipient will.
What does this mean?