Al,
What email account are you using in outlook? It may require a different outgoing setting than incoming. Example: yahoo, hotmail, ect..
In the outgoing part, you can go to advanced set-up and change it to a certain port # which may be required per provider. Make sure to check the "requires authentication" box. This may be the problem.
Try sending a message to yourself to check.
Tyler
www.nbcf.com
www.tylershoemakerracing.com