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 s

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

Found a typo, it is now working!

development.rb

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

Thanks for the support anyway!

Answer 3

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.