ListMail allows you to use an external SMTP server if you like. It sounds like you're trying to change the "Return-Path" header of the message. Some SMTP servers will not allow this to be anything other than @yourdomain.com. If you're using a gmail SMTP server then it might need to be you@gmail.com. Furthermore, some (few) hosts do not allow the "Send From Email" to be different than the Return-path. I suspect this might be true of gmail since it is a free service (isn't it? I'm not all-that familiar..) Anyways, this may not be your problem - we need to get connected first.
The host smtp.gmail.com does not seem to respond on port 465. While it does connect, there doesn't seem to be a service here. Port 25 is the default and I am getting a mail server connection here:
220 mx.gmail.com ESMTP g5sm800367wra
Depending on gmail's setup, you may need to use AUTH instead of authorize by checking email. When you set up a gmail account in Outlook, do you need to go into 'Advanced' and enable 'My outgoing server requires authentication' to send email through it? If you do, then you should probably use AUTH and not checking.
Likewise, pop.gmail.com is not responding on port 993 for 'Authorize by Checking Email'. Try changing the 'type' to POP3 instead of SSL.
When I try with another email that have smtp and pop3 which the smtp port is:25 , I get this error:
Most hosts respond on port 25 for SMTP. I am not sure why your secondary host didn't work there.
Generally, you should run ListMail on a commercial host that supports commercial opt-in email lists (
$7.95/mo). You can then use your host's provided SMTP server.