I am experiencing problems with Outlook. First, it will not capture certificates from signed e-mails, thus when encrypting or attempting to encrypt and email, this pop-up is displayed for the addressee;
Microsoft Outlook had problems encrypting this message because the following recipients had missing or invalid certificates, or conflicting or unsupported encryption capabilities:
Continue will encrypt and send the message (note: continue is grayed out) but the listed recipients may not be able to read it.
I have also noted that the Digitally signed email which have a certificate associated with it are not automatically capatured or associated with the senders email on my system.