Running into SMTP error when trying to send email in RoR app

Question

I've been desperately trying to send an email using the Action Mailer class in RoR, and even though the terminal shows that a message is being sent, it keeps returning with this error:

 et::SMTPAuthenticationError: 534-5.7.14 <https://accounts.google.com/ContinueSignIn?sarp=1&scc=1&plt=AKgnsbtOS

from /Users/abhasarya/.rvm/rubies/ruby-2.1.0/lib/ruby/2.1.0/net/smtp.rb:968:in `check_auth_response'
from /Users/abhasarya/.rvm/rubies/ruby-2.1.0/lib/ruby/2.1.0/net/smtp.rb:739:in `auth_plain'
from /Users/abhasarya/.rvm/rubies/ruby-2.1.0/lib/ruby/2.1.0/net/smtp.rb:731:in `authenticate'...

Here's what my mailer class looks like within app/mailers/my_mailer.rb:

class MyMailer < ActionMailer::Base
  default from: "[email protected]"

  def welcome_email(user) 
    @user = user

        mail(to: user.email,
             from: '[email protected]',
             subject: 'Welcome!')
  end
end

And here's what my config/application.rb file looks like:

config.action_mailer.delivery_method = :smtp
    config.action_mailer.smtp_settings = {

        address:              'smtp.gmail.com',
        port:                 587,
        #domain:               'gmail.com',
        user_name:            '[email protected]',
        password:             'my_password',
        authentication:       'plain',
        enable_starttls_auto: true  

        }

        config.action_mailer.default_url_options = {
            :host => "localhost",
            :port => 3000
        }

in my config/environments/development.rb file I also have these two lines:

  config.action_mailer.raise_delivery_errors = true
  config.action_mailer.perform_deliveries = true

My problem is that whenever I start the rails console (working in development, have no idea how to run in production), assign a user's email to the user variable then enter the command: MyMailer.welcome_email(user).deliver

the terminal says:

Rendered my_mailer/welcome_email.html.erb (11.7ms)
  Rendered my_mailer/welcome_email.text.erb (0.5ms)

Sent mail to [email protected] (923.1ms)
Date: Fri, 08 Aug 2014 13:54:38 -0400
From: [email protected]
To: [email protected]
Message-ID: <[email protected]>
Subject: Welcome!
Mime-Version: 1.0
Content-Type: multipart/alternative;
 boundary="--==_mimepart_53e50eded7355_2b0b8082dbf85068f";
 charset=UTF-8
Content-Transfer-Encoding: 7bit

but then renders the error. My views are simple enough that I didn't think I needed to include them here. I've desperately tried everything, including unlocking google captcha but still nothing works. I'd appreciate any help, all I want is for an email to get sent to the proper inbox. I'd love you forever if you can solve this issue!!!

Answer 1

The reason that you are seeing this error is that Google has blocked your IP. You will need to enable authorization for this IP.

Go to http://www.google.com/accounts/DisplayUnlockCaptcha and click continue.

Then again try to send email from the application, it should work. You will need to send email from your app within 10 min of visiting the above link. By visiting above link, Google will grant access to register new apps for 10 min.

Answer 2

I solved by doing the following:

1) Log into the Google Apps Admin portal and enable Less Secure Apps by checking "Allow users to manage their access to less secure apps" under Security preferences.

2) Login into the account that will serve as the mailer and turn "Allow less secure apps" to ON.

Most of the answers available on-line refer to step 2, but you cannot configure at a user level without the Admin turning the feature on.