Jun T. wrote:
But there is a (high) possibility that Gmail's server requires authentication (or certification) to connect to it.
I wonder if they're simply silently dropping emails in certain cases. I forgot earlier that I have a Gmail account. If I send an email from the command line on my home computer, which is on Comcast, the mail log shows that I successfully connect to Gmail, the message is sent and accepted by Gmail, but the email never arrives in my inbox. I've tried several times with the same result.
However, emails from a web server from work get through to Gmail without a problem. So I'd bet it's a case of them not delivering mail from Comcast IP addresses.
For grins, I also tried sending to my Yahoo email account from my home computer and their server at least refuses the connection and I get an error message stating that it's because it's a residential IP address.
In this case you need an SMTP client (=a software which directly sends the mail to the Gmail server) which supports authentication.
I think this might also be possible with Postfix by editing the configuration files. I know I had to set up authentication to send emails to my work address directly from my home computers, but I haven't been able to get the same thing to work with Gmail yet. If I get a chance, I'll look into it again later tonight.
charlie