How do I trigger CRES encryption in Microsoft Outlook using the confidential flag?
Encryption is typically triggered via a specific keyword in the subject line of an email by using an Outgoing content filter. We use the same procedure here but trigger on a header instead of the message subject.
An outgoing content filter should be created with the condition of "Other header".
Fill in "Header Name" box with "Sensitivity" (do not put quote marks in) and then select "Header Value" radio button with a Value of "Company-Confidential" (do not put quote marks in).
Select the appropriate action (i.e. Encrypt and Deliver Now) and add the content filter to the appropriate mail policies.
Apply the outgoing content filter to your default outbound mail policy and any other mail policies you may have.
Submit and Commit Changes
Validate your configuration is correct by sending a test email with the Confidential Flag checked.
Note: Additional sensitivities are available such as "private" and "personal". You would replace "private" with "Company-Confidential" in the above example if you wish to use the private sensitivity flag.
For more information on the Outlook Sensitivity Flag, refer to this page: