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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.
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
File “/usr/local/lib/python3.5/site-packages/django/core/mail/message.py”, line 292, in send
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
File “/usr/local/lib/python3.5/socket.py”, line 712, in createconnection
File “/usr/local/lib/python3.5/socket.py”, line 703, in create_connection
**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.
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:
and Turns On the Access for less secure apps.
I found out my Google password had special characters, which led to the /etc/postfix/sasl_passwd not being properly read. Simply the password (long one ofc) with up/lower case characters, numbers.
I also combined the settings found here if you still have trouble:
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.
I have the same problem. I fallowed your instructions. This works good on my local host. But when i use same on my live it give me error “535 Incorrect authentication data”. I believe that it is due to location of my live server. But what will be the solution for this?
Thanks in advance,