I had some troubles recently in sending e-mails with the Apple Mail client from multiple addresses through the Gmail SMTP server. Here is the issue. I have several mailboxes configured in Apple Mail, with several different e-mail addresses. I recently have added two more to the ones already configured but when I tried to send e-mails with the new addresses I realized that the e-mails were sent using a different e-mail address (one of those already configured). I have investigated the issue for a bit and finally found the solution…
