Unfortunately, support for encrypted messages in EWS protocol is not very good at all. To determine whether a message is encrypted (and/or signed) using S/MIME, use GetMessageInfo with EwsItemFields.AttachmentInfo, and check whether there is an attachment with a Content-Type of "application/pkcs7-mime" or "multipart/signed". Presence of such attachment indicates an S/MIME message. However, to learn anything more about the message, you would have to download it into an instance of MailMessage.