NW65sp8, gwia 8.0.0 may 13 09
I am trying to send email out via iphone through the gwia. I can connect via imap & check email just fine, but for some reason cannot send email. In testing on an external computer with outlook express I receive:

The message could not be sent because one of the recipients was rejected by the server. The rejected e-mail address was 'someaddress@gmail.com'. Subject 'test 5', Account: 'gwia.domain.org', Server: 'gwia.domain.org', Protocol: SMTP, Server Response: '550 #5.1.0 Address rejected.', Port: 25, Secure(SSL): No, Server Error: 550, Error Number: 0x800CCC79

I have made sure that "My server requires authentication" is checked. Logging is set to verbose. It does not list any of the attempts of the external domain emails, but it does list the internal emails I send just fine.

The odd thing is, if i send to address@mydomain.org via outlook express it seems to work without errors, but sending to say address@someexternaldomain.com always errors out. I was told this was "working fine a few weeks ago". I have tried this with multiple different external domains, same error.