CanCust,

Thank you for the headers. As i stated before, sending on behalf will not trigger the rule if it is using the person 2 address.

A possible work around in an exchange environment can possible resolve this. We have already confirmed person 1 sending on behalf of person 2 does not trigger the rule and person 1 is a delegate of person 2. ( Not sure if they have full access permissions)

Your engineers or whom ever is the administrator that controls permissions for each mailbox could give Full Access permissions of person 2's mailbox to person 1. if this is done person 1 can log directly into person 2's mailbox and use there settings to send Emails. This, in theory should trigger the rule.

What this does is changes the header file to reflect that person 2 is sending the email even though person 1 is the one actually doing it.

Hope this helps.