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This article describes how to overcome the problem with sending an encrypted email message to Internet recipient.
When you try to encrypt an email and send it to Internet recipient you receive the following warning:
Microsoft Outlook had problems encrypting this message because the following recipients had missing or invalid certificates, or conflicting or unsupported encryption capabilities: e-mail recipient
Where e-mail recipient represents a recipient that you are sending an e-mail message to. The only choices you are presented with are to Send Unencrypted or Cancel.
Microsoft Outlook does not contain valid information regarding recipient's capabilities to exchange encrypted correspondence, such as signing certificate.
Important: To resolve this issue it is necessary that digitally signed emails are exchanged first. Follow these steps to rectify the problem:
1. Double-click on the header of the digitally signed message you have received from Internet recipient. 2. Right-click on the sender's email address being displayed in the From: field and from the context menu choose Add to Outlook Contacts… 3. Customize contact information as necessary and go to Certificates tab. Verify that a certificate is displayed in Certificates (Digital IDs): field. 4. Once you are done with editing new contact properties click on Save and Close button.
Now, if you choose recipient's name from Outlook Contacts you should be able to send encrypted message.
It is required that both parties have valid digital certificates for email signing and encryption at the first place.