Britt Dickson wrote:

I just added these settings (was confused on 'then go back and
uncheck the box') to Outlook, created a test message, and it just
sits there in my out box. Remove the setting and it's exactly the
same as before. Won't send.

Enable diagnostic logging to see whan may be transpiring between Outlook and
the server.
http://support.microsoft.com/kb/300479/en-us
--
Brian Tillman