[Answer]-Django detect errors while sending mail

You can pick up some errors when you use fail_silently = False. Just wrap send_mail in try/except.

When i wanted more control over e-mail sending, then i stopped using django mailing completely and installed lamson instead (lamsonproject.org). You can basically create your own mail server with it, attach your django orm to it and provide detailed feedback about what has happened to your e-mails. If you insert some kind of downloadable content into those e-mails (like images), then you can even give hashes to images and verify this way if e-mail has been opened too. You could do that with django based email sending too. Lamson just gives bit more control over the what and how that goes on after you hit send button.