Hey guys, just found what’s going on with those errors.

The problem is that when you have activated the Google Authenticator Verification you also need to set up the 2-Step-Authentication in your gmail account.

Therefore visit https://www.google.com/settings/security - when you have done so, just go back to this page and click the “App Password” - Settings.

Select “Other (custom name)” and enter any name you like. Go ahead and copy the code and paste it to your projects settings.

Done! - This resolved all issues for me.

Greets P4rks!

1. Go to admin.google.com
2. From the admin console, select “Security”
3. Select “Basic settings”
4. Scroll down to “Less secure apps”
5. Go to settings for less secure apps ››
6. Check the radio button “Allow users to manage their access to less secure apps”
7. Save the changes
8. Open this link being sign in as the super administrator https://www.google.com/settings/security/lesssecureapps
9. Check the radio button Turn On the access for less secure apps
10. Unlock Captcha using this link https://accounts.google.com/DisplayUnlockCaptcha

I have everything settled up with Gmail, but sending inside Droplet (inside docker) I got:

Traceback (most recent call last):
File “<console>”, line 1, in <module>
File “/usr/local/lib/python3.5/site-packages/django/core/mail/init.py”, line 61, in sendmail
return mail.send()
File “/usr/local/lib/python3.5/site-packages/django/core/mail/message.py”, line 292, in send
return self.getconnection(failsilently).sendmessages([self])
File “/usr/local/lib/python3.5/site-packages/django/core/mail/backends/smtp.py”, line 100, in sendmessages
newconncreated = self.open()
File “/usr/local/lib/python3.5/site-packages/django/core/mail/backends/smtp.py”, line 58, in open
self.connection = connectionclass(self.host, self.port, connectionparams)
File “/usr/local/lib/python3.5/smtplib.py”, line 251, in _init__
(code, msg) = self.connect(host, port)
File “/usr/local/lib/python3.5/smtplib.py”, line 335, in connect
self.sock = self.getsocket(host, port, self.timeout)
File “/usr/local/lib/python3.5/smtplib.py”, line 306, in getsocket
self.sourceaddress)
File “/usr/local/lib/python3.5/socket.py”, line 712, in createconnection
raise err
File “/usr/local/lib/python3.5/socket.py”, line 703, in create_connection
sock.connect(sa)
**OSError: [Errno 99] Cannot assign requested address

I had the same problem. I guess it’s a gmail ban, because the Gmail send a mail with this link: https://support.google.com/mail/answer/14257?p=client_login&rd=1

The point is this: https://www.google.com/settings/security/lesssecureapps

You should change the “Access for less secure apps” to Enabled (it was enabled, I changed to disabled and than back to enabled). After a while I could send email.

I too ran into this problem today. I confirmed through my /var/log/mail.log that the connection happens, the username and password are sent (correct credentials), but the response is always:

535-5.7.8 Username and Password not accepted. Learn more at
535 5.7.8 http://support.google.com/mail/bin/answer.py?answer=14257 u8sm6322553qat.27 - gsmtp

I tried with an account that is in use in a different environment as well as with a brand new account within my google apps domain. Neither account worked.

For me the problem was not auth but the mail with valid URL inside.
I removed the urls and everything is fine.

There’s some changes from google security on Google Apps or gmail accounts.

To avoid the issue i had solved with the following steps:

1.Login into your account Gmail or Google Apps then goto:

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

and Turns On the Access for less secure apps.

You can have also this issue if you use Two Factor Sign-In. If so, you need to create a separate access to use for applications. you can manage them under https://myaccount.google.com/apppasswords