Rails 4 Net::SMTPAuthenticationError: 535 #5.7.0 Authentication failed

Question

I\'m building a email list for a student organization at my University. The organization has around 6000 members and to avoid costs I\'ve received permission to use the scho

Answer 1

My issue was resolved by following steps.

config.action_mailer.default :charset => "utf-8"
config.action_mailer.perform_deliveries = true
config.action_mailer.raise_delivery_errors = true
config.action_mailer.delivery_method = :smtp
config.action_mailer.smtp_settings = {
    address: 'smtp.gmail.com',
    port: 587,
    domain: 'mysite.com',
    user_name: myemail@gmail.com,
    password: mypassword,
    authentication: 'plain',
    enable_starttls_auto: true
}

As google will try to block your sign-in if you have turned off access for less secure apps in your accounts settings. Therefore, follow this link and "Turn on" access for less secure apps.

Answer 2

Should ":domain" point to "school.edu" instead of "herokuapp.com"? I know when you set smtp for gmail via action_mailer settings, you have something like:

config.action_mailer.smtp_settings = {
    :address              => 'smtp.gmail.com',
    :port                 => 587,
    :domain               => 'gmail.com',
    :user_name            => 'example@gmail.com',
    :password             => 'example_password',
    :authentication       => 'login',
    :enable_starttls_auto => true
  }

Answer 3

Should the domain contain "http://" ?

Answer 4

Create a file setup_mail.rb in the folder config/initializers/ and put the code:-

ActionMailer::Base.delivery_method = :smtp
ActionMailer::Base.perform_deliveries = true
ActionMailer::Base.smtp_settings = {
  :address   => "smtp.school.edu",
  :domain => 'myapp.herokuapp.com',
  :port      => 25,
  :user_name => "account@school.edu",
  :password  => "mypassword", 
  :authentication => :plain,
  :enable_starttls_auto => true
}
ActionMailer::Base.default_url_options[:host] = "myapp.herokuapp.com"

Answer 5

Try adding openssl_verify_mode => 'none' to your action mailer settings:

config.action_mailer.smtp_settings = 
{
    :address   => "smtp.school.edu",
    :port      => 25, 
    :enable_starttls_auto => true, 
    :user_name => "account@school.edu",
    :password  => "mypassword", 
    :authentication => 'login',
    :domain => 'http://myapp.herokuapp.com/',
    :openssl_verify_mode => 'none'
}

Granted, we are using Rails 3, but this worked for me. The issue for us was that our certificates are self-signed and the library Rails uses considers that to be a problem. Here is an article that talks about the option.