It does not really have to do with Django, it has to do with OAuth which Google 
just started enforcing in gmail, you need to relax the security level on the 
gmail account you are using on this page:

        https://www.google.com/settings/security/lesssecureapps

François

> On Feb 9, 2015, at 8:25 PM, bradford li <bradfor...@gmail.com> wrote:
> 
> I am trying to have django send emails but I am getting this error:
> 
>     Traceback (most recent call last):
>       File "<console>", line 1, in <module>
>       File "/Library/Python/2.7/site-packages/django/core/mail/__init__.py", 
> line 62, in send_mail
>         return mail.send()
>       File "/Library/Python/2.7/site-packages/django/core/mail/message.py", 
> line 286, in send
>         return self.get_connection(fail_silently).send_messages([self])
>       File 
> "/Library/Python/2.7/site-packages/django/core/mail/backends/smtp.py", line 
> 92, in send_messages
>         new_conn_created = self.open()
>       File 
> "/Library/Python/2.7/site-packages/django/core/mail/backends/smtp.py", line 
> 59, in open
>         self.connection.login(self.username, self.password)
>       File 
> "/System/Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7/smtplib.py",
>  line 615, in login
>         raise SMTPAuthenticationError(code, resp)
>     SMTPAuthenticationError: (534, '5.7.9 Application-specific password 
> required. Learn more at\n5.7.9 
> http://support.google.com/accounts/bin/answer.py?answer=185833 
> v14sm3323298pbs.11 - gsmtp')
> 
> The link suggested my to perform a 2-step verification which I did but still 
> no results.
> 
> In my settings.py
> 
>     EMAIL_USE_TLS = True
>     EMAIL_HOST = 'smtp.gmail.com'
>     EMAIL_HOST_USER = 'em...@gmail.com'
>     EMAIL_HOST_PASSWORD = 'password'
>     EMAIL_PORT = 587
> 
> I tried testing this in django shell but got the error shown above:
> 
>     >>> from django.core.mail import send_mail
>     >>> from django.conf import settings
>     >>> sub = "sup man"
>     >>> msg = "char lisss"
>     >>> from_user = settings.EMAIL_HOST_USER
>     >>> to = ["em...@email.com"]
>     >>> send_mail(sub,msg,from_user,to, fail_silently=False)
> 
> 
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