Ruby/Rails ActionMailer not working with NTLM

Question

I am setting up a mailer in my project and I am having difficulties sending mail through Exchange SMTP server.

I have installed the gem ruby-ntlm but I am still getting unrecognized authentication type.

This is my code

environment.rb

# Load the Rails application.
require File.expand_path('../application', __FILE__)
require 'ntlm/smtp'

# Initialize the Rails application.
Rails.application.initialize!

notifier.rb

class Notifier < ActionMailer::Base
  default :from => "[e-mail]"

  def test
    mail(:to => "[e-mail]", :subject => "Test subject").deliver
  end
end

development.rb

  config.action_mailer.delivery_method = :smtp
  config.action_mailer.smtp_settings = {
    :address => "**REMOVED**",
    :port => 587, 
    :domain => "CMSAD",   
    :user_name => "**REMOVED**", 
    :password => "**REMOVED**", 
    :authentification => :ntlm,
    :enable_starttls_auto => false
  }

Rails console test

Notifier#test: processed outbound mail in 5591.8ms
Net::SMTPAuthenticationError: 504 5.7.4 Unrecognized authentication type

        from /home/stephen/.rvm/rubies/ruby-2.1.0/lib/ruby/2.1.0/net/smtp.rb:968:in `check_auth_response'
        from /home/stephen/.rvm/rubies/ruby-2.1.0/lib/ruby/2.1.0/net/smtp.rb:739:in `auth_plain'
        from /home/stephen/.rvm/rubies/ruby-2.1.0/lib/ruby/2.1.0/net/smtp.rb:731:in `authenticate'
        from /home/stephen/.rvm/rubies/ruby-2.1.0/lib/ruby/2.1.0/net/smtp.rb:566:in `do_start'
        from /home/stephen/.rvm/rubies/ruby-2.1.0/lib/ruby/2.1.0/net/smtp.rb:519:in `start'
        from /home/stephen/.rvm/gems/ruby-2.1.0/gems/mail-2.6.3/lib/mail/network/delivery_methods/smtp.rb:112:in `deliver!'
        from /home/stephen/.rvm/gems/ruby-2.1.0/gems/mail-2.6.3/lib/mail/message.rb:2141:in `do_delivery'
        from /home/stephen/.rvm/gems/ruby-2.1.0/gems/mail-2.6.3/lib/mail/message.rb:236:in `block in deliver'
        from /home/stephen/.rvm/gems/ruby-2.1.0/gems/actionmailer-4.1.8/lib/action_mailer/base.rb:527:in `block in deliver_mail'
        from /home/stephen/.rvm/gems/ruby-2.1.0/gems/activesupport-4.1.8/lib/active_support/notifications.rb:159:in `block in instrument'
        from /home/stephen/.rvm/gems/ruby-2.1.0/gems/activesupport-4.1.8/lib/active_support/notifications/instrumenter.rb:20:in `instrument'
        from /home/stephen/.rvm/gems/ruby-2.1.0/gems/activesupport-4.1.8/lib/active_support/notifications.rb:159:in `instrument'
        from /home/stephen/.rvm/gems/ruby-2.1.0/gems/actionmailer-4.1.8/lib/action_mailer/base.rb:525:in `deliver_mail'
        from /home/stephen/.rvm/gems/ruby-2.1.0/gems/mail-2.6.3/lib/mail/message.rb:236:in `deliver'
        from /media/development/Foostix-web/app/mailers/notifier.rb:5:in `test'
        from /home/stephen/.rvm/gems/ruby-2.1.0/gems/actionpack-4.1.8/lib/abstract_controller/base.rb:189:in `process_action'
... 15 levels...
        from /home/stephen/.rvm/gems/ruby-2.1.0/gems/railties-4.1.8/lib/rails/commands/console.rb:9:in `start'
        from /home/stephen/.rvm/gems/ruby-2.1.0/gems/railties-4.1.8/lib/rails/commands/commands_tasks.rb:69:in `console'
        from /home/stephen/.rvm/gems/ruby-2.1.0/gems/railties-4.1.8/lib/rails/commands/commands_tasks.rb:40:in `run_command!'
        from /home/stephen/.rvm/gems/ruby-2.1.0/gems/railties-4.1.8/lib/rails/commands.rb:17:in `<top (required)>'
        from /home/stephen/.rvm/gems/ruby-2.1.0/gems/activesupport-4.1.8/lib/active_support/dependencies.rb:247:in `require'
        from /home/stephen/.rvm/gems/ruby-2.1.0/gems/activesupport-4.1.8/lib/active_support/dependencies.rb:247:in `block in require'
        from /home/stephen/.rvm/gems/ruby-2.1.0/gems/activesupport-4.1.8/lib/active_support/dependencies.rb:232:in `load_dependency'
        from /home/stephen/.rvm/gems/ruby-2.1.0/gems/activesupport-4.1.8/lib/active_support/dependencies.rb:247:in `require'
        from /media/development/Foostix-web/bin/rails:8:in `<top (required)>'
        from /home/stephen/.rvm/gems/ruby-2.1.0/gems/activesupport-4.1.8/lib/active_support/dependencies.rb:241:in `load'
        from /home/stephen/.rvm/gems/ruby-2.1.0/gems/activesupport-4.1.8/lib/active_support/dependencies.rb:241:in `block in load'
        from /home/stephen/.rvm/gems/ruby-2.1.0/gems/activesupport-4.1.8/lib/active_support/dependencies.rb:232:in `load_dependency'
        from /home/stephen/.rvm/gems/ruby-2.1.0/gems/activesupport-4.1.8/lib/active_support/dependencies.rb:241:in `load'
        from /home/stephen/.rvm/rubies/ruby-2.1.0/lib/ruby/site_ruby/2.1.0/rubygems/core_ext/kernel_require.rb:54:in `require'
        from /home/stephen/.rvm/rubies/ruby-2.1.0/lib/ruby/site_ruby/2.1.0/rubygems/core_ext/kernel_require.rb:54:in `require'

However this works....

smtp = Net::SMTP.new('**REMOVED**', 587)
smtp.debug_output = $stdout
smtp.enable_starttls_auto#skip if not needed
smtp.start("CMSAD", "**REMOVED**", "**REMOVED**", :ntlm)

TLS connection started
<- "EHLO CMSAD\r\n"
-> "250-**REMOVED** Hello [**REMOVED**]\r\n"
-> "250-SIZE 104857600\r\n"
-> "250-PIPELINING\r\n"
-> "250-DSN\r\n"
-> "250-ENHANCEDSTATUSCODES\r\n"
-> "250-AUTH GSSAPI NTLM LOGIN\r\n"
-> "250-8BITMIME\r\n"
-> "250-BINARYMIME\r\n"
-> "250 CHUNKING\r\n"
<- "AUTH NTLM **REMOVED**==\r\n"
-> "334 **REMOVED**\r\n"
<- **REMOVED**\r\n"
-> "235 2.7.0 Authentication successful\r\n"
 => #<Net::SMTP **REMOVED** started=true>

Answer 1

This is because you haven't included the ntlm library.

Add the NTLM SMTP library to your config/environment.rb file

# Load the Rails application.
require File.expand_path('../application', __FILE__)

require 'ntlm/smtp' # ADD THIS LINE HERE

# Initialize the Rails application.
Rails.application.initialize!

Answer 2

Add the ruby-ntlm gem to your Gemfile and run bundle install.

Gemfile:

  gem 'ruby-ntlm'

bundle install

Add the NTLM SMTP library to your config/environment.rb file.

# Load the rails application
require File.expand_path('../application', __FILE__)
require 'ntlm/smtp'

# Initialize the rails application
RailsApp::Application.initialize!

Set up your environment file to authenticate with NTLM.

config.active_support.deprecation = :notify
config.action_mailer.delivery_method = :smtp
config.action_mailer.smtp_settings = {
  :address => '<your-email-server>',          # mail.example.com
  :domain => '<your-domain>',                 # example.com
  :user_name => '<your-username>',            # user.name
  :password => '<your-unencrypted-password>', # p@ssw0rd
  :port => 25,
  :authentication => :ntlm
}

Finally, make sure you change your default from whatever email address you’ve been using to reflect the new Microsoft Exchange account, or you’ll receive a 5.7.1 Client does not have permissions to send as this sender error.

Answer 3

Found a typo, it is now working!

development.rb

Change :authentification => :ntlm to :authentication => :ntlm

Thanks for the support anyway!