Can you send the complete log when sending the email. You can prevent the window that appears when sending mail by teaching factotum the passwords for your mail provider.
Just so we can see the complete conversation with gmail
and get a better understanding of what went wrong.
I assume you have worked you way through this:
http://www.plan9.bell-labs.com/wiki/plan9/mail_configuration/index.html
particularly with reference to the section on SMTP TLS auth
-Steve
