I am finding this very odd. This piece of code doesn't send two email messages. The first way using send_mail is working find. While using EmailMultiAlternatives isn't sending any messages. I've already debugged user.email, and it is using failed email addresses, in case of the obvious. This code runs from a management command.
send_mail("test", "test", "test@test.com", ["my@email.com"])
msg = EmailMultiAlternatives(
self.TITLE,
self.generate_text_content(cans, cants, "week"),
settings.NOREPLY_EMAIL, [user.email])
msg.attach_alternative(self.generate_html_content(cans, cants, "week")
,"text/html")
msg.send(fail_silently=False)