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

8
votes

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 schools emails servers and they have created an account for me.

I have tested the the account using my mail client and everything seems to be working fine, but when I try to send through my Rails 4 app I get the error: 

Net::SMTPAuthenticationError: 535 #5.7.0 Authentication failed

I have it configured like so:

application.rb

config.action_mailer.smtp_settings = 
{
    :address   => "smtp.school.edu",
    :port      => 25, 
    :enable_starttls_auto => true, 
    :user_name => "[email protected]",
    :password  => "mypassword", 
    :authentication => 'login',
    :domain => 'http://myapp.herokuapp.com/' 
}

Again the credentials are all correct, I have tested it through my mail client and have also sat down with the server admin to confirm everything looks right in my configuration as far as port and credentials.

I've been told the smtp server is "wide open to the public" and there is nothing blocking a connection and we have checked their logs and they haven't even seen an attempt to connect from my app.

Anyone have any clue what is going wrong here? Is there some setting I dont know about that could be off?

5
ruby-on-railsemailruby-on-rails-4herokuactionmailer
Can you post the logs from the action after the mail is sent . – Caffeine Coder
Also do keep checking the spam folder , as testing a certain functionality time and again is treated as spam by google . – Caffeine Coder
@CaffeineCoder Im not using google. – Deekor
In your mailer file what is the email that you are using ? make sure it's the same as Check if the port is open or accessible, – 0bserver07

5 Answers

6
votes

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 => "[email protected]",
    :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.

2
votes

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            => '[email protected]',
    :password             => 'example_password',
    :authentication       => 'login',
    :enable_starttls_auto => true
  }
1
votes

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 => "[email protected]",
  :password  => "mypassword", 
  :authentication => :plain,
  :enable_starttls_auto => true
}
ActionMailer::Base.default_url_options[:host] = "myapp.herokuapp.com"
0
votes

Should the domain contain "http://" ?

0
votes

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: [email protected],
    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.