Net::SMTPAuthenticationError when sending email from Rails app (on staging environment)

Question

I am sending email from my Rails application. It works well on development environment, but fails on staging. I get the following error:

Net::SMTPAuthenticationError (534-5.7.14 <https://accounts.google.com/ContinueSignIn?plt=AKgnsbtdF0yjrQccTO2D_6)

Note, that my I don't have a domain name for my staging.

Here are my settings in staging.rb

config.action_mailer.delivery_method = :smtp
config.action_mailer.default_url_options = { :host => "my.ip.addr.here:80" }
config.action_mailer.smtp_settings = {
      :address => "smtp.gmail.com",
      :port => 587,
      :domain => 'my.ip.addr.here:80'
      :user_name => "[email protected]",
      :password => "my_email_password",
      :authentication => 'login'
}

Please, help.

Edit.

After adding :tls => true option I get

OpenSSL::SSL::SSLError (Unrecognized SSL message, plaintext connection?)

And then I changed port to 25 and now I get this (with 30 seconds delay):

Timeout::Error (execution expired)

Seize

I've copied the url in error (google probably thought in advance for us) to browser. Entered my password and in the panel I've seen switched the possibility to make requests not only from trusted sites. – Cotangent

Answer 1

I had the same problem: emails were sent from development, but not from production (where I was getting Net::SMTPAuthenticationError). This drove me to conclusion that the problem was not with my app's configuration, but with Google.

Reason: Google was blocking access from unknown location (app in production)

Solution: Go to http://www.google.com/accounts/DisplayUnlockCaptcha and click continue (this will grant access for 10 minutes for registering new apps). After this my app in production started sending emails ;)

Cymose

That's actually is the correct way to solve it (although it may put your account at risk). But it works. – Morpheus

Also do not forget allow account-access here:: google.com/settings/security/lesssecureapps – Wicket

I was able to avoid the lesssecureapps setting by using multifactor authentication and enabling an app-specific password for my rails server. – Rama

Probably better to use a service like Mandrill for sending emails in a production environment – Bobbibobbie

I have turned on lesssecureapps account setting and went to DisplayUnlockCaptcha page and pressed OK, sent email through rails but received the same error Net::SMTPAuthenticationError ...ContinueSignIn.... Then I tried to do the same after 10 minutes and it started working. – Gondola

I'm guessing I only have to do this every time I deploy, am I correct? – Hygroscope

@ChrisBeck, can you explain the whole process ? – Nowhere

Answer 2

Solved! I simply changed password for my gmail account and somehow errors disappeared.

After dozen of changes, the final settings I ended up with are:

config.action_mailer.delivery_method = :smtp
config.action_mailer.default_url_options = { :host => "my.ip.addr.here" }
config.action_mailer.smtp_settings = {
      :address => "smtp.gmail.com",
      :port => 587,
      :domain => 'my.ip.addr.here:80',
      :user_name => "[email protected]",
      :password => "my_email_password",
      :authentication => :plain,
      :enable_starttls_auto => true
}

Seize

Thank you! This problem was causing me a lot of headache, and in the end what I needed to do was change my google account password after using these settings and setting the allow less secure apps option in the google account settings. – Perea

After setting 'allow less secure apps' and tell google to trust my device (server's IP) and waiting for over 24 hrs... a simple change of password fixed my gmail authentication issues. someone at google should probably fix that. ;) – Nymphomania

I was facing the same issue. I had already enabled lessecureapps but it wont fix. I simply changed my password and it worked like a charm. :) – Plexiglas

Answer 3

This solution is working for me:

config.action_mailer.delivery_method = :smtp
  config.action_mailer.default_url_options = { host:'localhost', port: '3000' }
  config.action_mailer.perform_deliveries = true
  config.action_mailer.raise_delivery_errors = true
  config.action_mailer.default :charset => "utf-8"
  config.action_mailer.smtp_settings = {
      :address => "smtp.gmail.com",
      :port => 587,
      :domain => 'localhost:3000',
      :user_name => "[email protected]",
      :password => "password",
      :authentication => :plain,
      :enable_starttls_auto => true
  }

It's true that Google will block your sign-in attempt but You can change your settings at https://www.google.com/settings/security/lesssecureapps so that your account is no longer protected by modern security standards.

Prologue

Is there a way around doing this? Is it possible to register you app with google, for instance? – Bramwell

Answer 4

The above solution provided the correct settings (which I already had) but did not solve the issue. After continued attempts, I kept getting the same error. Turns out, I had to "clear the CAPTCHA" from the web. See the gmail documentation for details.

You can also jump right to the "clear the CAPTCHA" page here.

Culmiferous

Direct link to "clear the CAPTCHA" page: accounts.google.com/DisplayUnlockCaptcha – Krell

Answer 5

go to following link and turn on https://www.google.com/settings/security/lesssecureapps

Cartel

Answer 6

I had the same problem.

---

Solution:

• You can turn on less secure apps option (at here).
  https://myaccount.google.com/lesssecureapps

• And unlock Captcha (link):
  https://accounts.google.com/DisplayUnlockCaptcha

Monocular

Answer 7

A lot later but just in case it helps anyone.. Just called Google Apps Help Center and they instructed to change the lesssecureapps setting (as everyone else) but also to change the port to 465.

In my case, that did the trick!

Dambro

Answer 8

To resolve this issue:

• If you see: Net::SMTPAuthenticationError (535-5.7.8 Username and Password not accepted.), then you need to allow less secure apps to login your google account. To enable less secure apps login follow: https://myaccount.google.com/lesssecureapps?. But will allow all apps to login. If you want to customize it refer : https://support.google.com/a/answer/6260879?hl=en

• Then may be possible you will get Net::SMTPAuthenticationError (534-5.7.14), so to resolve this refer: pli=1http://www.google.com/accounts/DisplayUnlockCaptcha. After that click the continue from the page you get redirected. It will verify your Captcha and your app will get verified to use your google account to send emails.

NOTE: Please make sure you'r using correct credentials of your gmail account.

If you'r not willing to allow all the apps please refer: https://support.google.com/a/answer/6260879?hl=en. From the link go to Use alternatives to less secure apps, this will guide you to an alternative way to Allow Less Secure apps access to your google account.

Variorum

This fixed it for me thanks for the info. – Diameter

Answer 9

The accepted answer seems very old, I don't know if at that time the followin (better) solution was existing:

• Go to https://myaccount.google.com/u/0/apppasswords
• Generate a new password for you app
• Replace the personal password with the generated password in config.action_mailer.smtp_settings

Now, sending emails works perfectly!

Puerile

Answer 10

Hello this also worked for me and so if someone is still having a problem try this out.

Make sure you have figaro in your gemfile. To save sensitive information such as username and password as environment variables

gem 'figaro'

And in your config/environments/development.rb , paste the codes below using smtp as method delivery

 config.action_mailer.delivery_method = :smtp

SMTP settings for gmail

  config.action_mailer.smtp_settings =
  {
    :address=> "smtp.gmail.com",
    :port => 587,
    :user_name => ENV['gmail_username'],
    :password=> ENV['gmail_password'],
    :authentication=> "plain",
    :enable_starttls_auto=>true
  }


config.action_mailer.default_url_options = { host: "locahost:3000" }

In your config directory create a file called application.yml and add the codes below.

gmail_username: '[email protected]' 
gmail_password: "your_example_email_password_here"

You must use your email and password for authentication in the file.

Donkey

config.action_mailer.default_url_options = { host: "localhost:3000" } – Donkey

Answer 11

I also faced the problem, and after some research in Gmail setting, I found the solution:

1. In gmail, go to settings.

2. Select "Forwarding and POP/IMAP" tab.

3. In the IMAP access section, select "Enable IMAP".

Squinty

Answer 12

I had the same problem and after some trial and errors, have come to this resolution which is an option to be enabled in google:

Click https://www.google.com/settings/u/0/security/lesssecureapps

Enable 'Access for less secure apps' here by logging in with the email address you have provided in smtp configuration.

Orthotropous