My system administrator has convinced me to try OS X Mail rather than Outlook. I believe that Outlook, while having its warts as a mail client (due to its MS heritage), does have a great deal of power that is unappreciated by those who have not used it. In any case, I am running into some of those limitations. The rules capability appears far more powerful in Outlook. I need to implement the following rule: From contains A or B or C Subject contains D or E or F Message contents contains G or H Can this even be done? I am willing to have multiple rules to unwind the logic, but I am not convinced it will get the same result. Any ideas?