I understand the difference between these two things, and how to configure one or the other. I have a boss who wants his assistant to be able to Send AS SOMETIMES and Send On Behalf Of other times. Is there a simple way the assistant can toggle back and forth? Also, how will the destination of the Sent Item work? Will the Sent Item go to the assistants Sent Items folder? Will it go to the boss' Sent Items folder? Is there a way to specify that? Is there a way, AT ALL TIMES, to copy the Sent Item to the assistants Sent Items AND the boss' Sent Items folders? Thanks in advance.Thomas Murray

I understand the difference between these two things, and how to configure one or the other. I have a boss who wants his assistant to be able to Send AS SOMETIMES and Send On Behalf Of other times. Is there a simple way the assistant can toggle back and forth? Also, how will the destination of the Sent Item work? Will the Sent Item go to the assistants Sent Items folder? Will it go to the boss' Sent Items folder? Is there a way to specify that? Is there a way, AT ALL TIMES, to copy the Sent Item to the assistants Sent Items AND the boss' Sent Items folders? Thanks in advance.Thomas Murray

Its one or the other. If you add both and SEND AS and SEND On Behalf, it should always show it as SEND AS regardless. For the other question, see: http://support.microsoft.com/kb/972148 This works for Outlook 2010 SP1 as well.

Duplicate. See: http://social.technet.microsoft.com/Forums/en-US/exchangesvradmin/thread/8e7cbed1-dc0c-4426-bc4f-e31ca994a4dc