This feature requires Microsoft Windows 2000 or Microsoft Windows Millennium Edition (Me).
Sending messages with secure receipt requests verifies that the recipient is validating your digital signature (the certificate you applied to a message).
Send a single message with a secure receipt request
Send all messages with a secure receipt request
From the main Outlook window, on the Tools menu, click Options, and then click the Security tab.
Select the Add digital signature to outgoing messages check box.
Select the Request secure receipts for all S/MIME signed messages check box.