not getting the transcript mail,

[f1-outsourcing]

I am running webchat war on a local ip range without gateway. I thought maybe this was preventing the email with transcript being send out. But when I looked at the tcpdump log, I saw it communicate with the openfire instance.
So I assume the message is being send from the openfire server. I can send the test email message from openfire.
I don't see any connection attempt in the mail server log files.