Unable to send mail through

I have recently become unable to send any e-mail from my Django app hosted on a DO droplet through Any time I try, I get the following error message:

SMTPAuthenticationError (535, ‘5.7.8 Username and Password not accepted. Learn more at\n5.7.8 sh5sm32272477pbc.21 - gsmtp’)

Which is weird, because the username and password used works perfectly when I try to log in manually, or when sending through the exact same Django app from localhost.

I have also tried going through , as mentioned in the Google support answer.

I have been sending at maximum a couple of hundred e-mail in total from that account, with maybe ~10 a day - so abuse seems to be out of the question for me. I should mention that the account is a paid Google Apps account.

The fact that I can use the exact same settings while using localhost as a server, plus the fact that this error has only appeared recently, makes me think that the error might have something to do with Digital Ocean.

Do you have any ideas about what might cause this?

Thanks and with the best regards, Martin

Ps. for good measure, here are my smtp settings, minus the password (which I am 100% sure is correct):


Show comments

Submit an answer

This textbox defaults to using Markdown to format your answer.

You can type !ref in this text area to quickly search our full set of tutorials, documentation & marketplace offerings and insert the link!

Sign In or Sign Up to Answer

These answers are provided by our Community. If you find them useful, show some love by clicking the heart. If you run into issues leave a comment, or add your own answer to help others.

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 - 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
  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
  9. Check the radio button Turn On the access for less secure apps
  10. Unlock Captcha using this link

I had the same problem. I guess it’s a gmail ban, because the Gmail send a mail with this link:

The point is this:

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.