The error message that I receive is: "The handshake failed due to an unexpected packet format." I've checked the system logs and there is no additional information. Information on configuring SMTP to work with Outlook Live can be found here: http://help.outlook.com/en-us/140/cc875899.aspx?ref=search. It's important to note that I haven't had any problems getting other web applications to work with Outlook Live SMTP, most notably DotNetNuke and WordPress.

Thanks, bR