Django Email Timeout on Production Server - django

Question

I recently deployed a site that I developed in Django onto a production server running Ubuntu 19.10 and Apache/2.4.41. I've been able to get my site functioning in every respect with the exception of sending emails using SMTP. When running my site on the development server on my local machine Django is able to send emails without issue, but on the production server any attempt by the site to send an email hangs and eventually results in a server error. In Apache's error.log I'm finding this at the bottom of the traceback: TimeoutError: [Errno 110] Connection timed out. Curiously, this problem persists if I turn on port 8000 and run this site with Django's development server from the remote machine.
I've made sure that my settings.py is configured properly (as I mentioned this works fine on my local computer).
settings.py
...
EMAIL_BACKEND = 'django.core.mail.backends.smtp.EmailBackend'
EMAIL_HOST = 'smtp.gmail.com'
EMAIL_PORT = 587
EMAIL_USE_TLS = True
EMAIL_HOST_USER = site_config.get('EMAIL_USER')
EMAIL_HOST_PASSWORD = site_config.get('EMAIL_PASS')
My suspicion has been that the issue must be related to my firewall blocking outgoing traffic on port 587, but I double checked my settings and couldn't see how this could be the case. I even manually set rules to allow outgoing traffic on port 587 and 25 to be sure, but did not have any success.
ufw status
Status: active
Logging: on (low)
Default: deny (incoming), allow (outgoing), disabled (routed)
New profiles: skip
To Action From
-- ------ ----
22/tcp ALLOW IN Anywhere
80/tcp ALLOW IN Anywhere
22/tcp (v6) ALLOW IN Anywhere (v6)
80/tcp (v6) ALLOW IN Anywhere (v6)
587 ALLOW OUT Anywhere
25/tcp ALLOW OUT Anywhere
587 (v6) ALLOW OUT Anywhere (v6)
25/tcp (v6) ALLOW OUT Anywhere (v6)
I've tried testing that I'm able to establish SMTP connections at all using the advice offered in this post and got a timeout error there as well.
All of this seems to point to some sort of error in the way I've configured my firewall and/or Apache, but, after reading a number of posts on SO and elsewhere, I feel I've run out of ideas.
Lastly, here's what I'm seeing in the error log:
/var/log/apache2/error.log
log: ERROR - Internal Server>
Traceback (most recent call last):
File "/home/user/mysite/venv>
response = get_response(request)
File "/home/user/mysite/venv>
response = self.process_exception_by_middleware(e,>
File "/home/user/mysite/venv>
response = wrapped_callback(request, *callback_arg>
File "/home/user/mysite/venv>
return self.dispatch(request, *args, **kwargs)
File "/home/user/mysite/venv>
return bound_method(*args, **kwargs)
File "/home/user/mysite/venv>
response = view_func(request, *args, **kwargs)
File "/home/user/mysite/venv>
return super().dispatch(*args, **kwargs)
File "/home/user/mysite/venv>
return handler(request, *args, **kwargs)
File "/home/user/mysite/venv>
return self.form_valid(form)
File "/home/user/mysite/venv>
form.save(**opts)
File "/home/user/mysite/venv>
user_email, html_email_template_name=html_email_te>
File "/home/user/mysite/venv>
email_message.send()
File "/home/user/mysite/venv>
return self.get_connection(fail_silently).send_mes>
File "/home/user/mysite/venv>
new_conn_created = self.open()
File "/home/user/mysite/venv>
self.connection = self.connection_class(self.host,>
File "/usr/lib/python3.7/smtplib.py", line 251, in _>
(code, msg) = self.connect(host, port)
File "/usr/lib/python3.7/smtplib.py", line 336, in c>
self.sock = self._get_socket(host, port, self.time>
File "/usr/lib/python3.7/smtplib.py", line 307, in _>
self.source_address)
File "/usr/lib/python3.7/socket.py", line 727, in cr>
raise err
File "/usr/lib/python3.7/socket.py", line 716, in cr>
sock.connect(sa)
TimeoutError: [Errno 110] Connection timed out
I'd happily add more information to this if there is anything important that I've left out. This is my first attempt at deploying a site to a remote server so keep in mind this is all a bit new to me.

Answer 1

If you use Linode to deploy your website, note that the port 587 is blocked by default.
It took me 2 days to figure it out.