How to send mail via Exchange Server 2013 on Rails 2.1.1?

Question

We have an old application that we built 6 years ago. We get this error "504 5.7.4 Unrecognized authentication type" after we upgrade our mail server from Exchange Server 2007 into Exchange Server 2013.

Is there anyway to solve this error without upgrade the rails version?

OS
Microsoft Windows Server 2003 Standard Edition Service Pack 2

InstantRails 2.0

environment.rb

config.action_mailer.delivery_method = :smtp
config.action_mailer.smtp_settings = {
    :address => "mail-server",
    :port => 25,
    :domain => "domain.com",
    :authentication => :login,
    :user_name => "username",
    :password => "password",
    :enable_strttls_auto => true,
    :openssl_verify_mode => "none"
}
config.action_mailer.raise_delivery_errors = true
config.action_mailer.perform_deliveries = true
config.action_mailer.default_charset = 'utf-8'

user_mailer.rb

  #using fake outlook account
  def test_notification_fake
    @subject = "Dev - APP | Testing Email_fake."
    @body = {}
    # Give body access to the user information.
    @recipients = '[email protected]'
    @bcc = $adminemail
    @content_type = "text/html"
    @from = 'APP | do-not-reply email <[email protected]>'
  end

  #using real outlook account
  def test_notification_real        
    @subject = "Dev - APP | Testing Email_real."
    @body = {}
    # Give body access to the user information.
    @recipients = '[email protected]'
    @bcc = $adminemail
    @content_type = "text/html"
    @from = 'APP | do-not-reply email <[email protected]>'
  end

master_controller.rb

def index
    UserMailer.deliver_test_notification_fake    
    UserMailer.deliver_test_notification_real

gem env

C:\InstantRails\rails_apps>gem env
RubyGems Environment:
  - RUBYGEMS VERSION: 1.4.0
  - RUBY VERSION: 1.8.6 (2007-09-24 patchlevel 111) [i386-mswin32]
  - INSTALLATION DIRECTORY: C:/InstantRails/ruby/lib/ruby/gems/1.8
  - RUBY EXECUTABLE: C:/InstantRails/ruby/bin/ruby.exe
  - EXECUTABLE DIRECTORY: C:/InstantRails/ruby/bin
  - RUBYGEMS PLATFORMS:
    - ruby
    - x86-mswin32-60
  - GEM PATHS:
     - C:/InstantRails/ruby/lib/ruby/gems/1.8
  - GEM CONFIGURATION:
     - :update_sources => true
     - :verbose => true
     - :benchmark => false
     - :backtrace => false
     - :bulk_threshold => 1000
     - :gempath => ["C:/InstantRails/ruby/lib/ruby/gems/1.8"]
     - :sources => ["http://gems.rubyforge.org/", "http://gems.github.com/", "ht
tp://rubygems.org/", "http://gemcutter.org/"]
     - "gem" => "--no-rdoc --no-ri"
  - REMOTE SOURCES:
     - http://gems.rubyforge.org/
     - http://gems.github.com/
     - http://rubygems.org/
     - http://gemcutter.org/

gem list

C:\InstantRails\rails_apps>gem list

*** LOCAL GEMS ***

actionmailer (2.1.1, 2.0.2)
actionpack (2.1.1, 2.0.2)
activerecord (2.1.1, 2.0.2)
activerecord-odbc-adapter (2.0)
activerecord-sqlserver-adapter (1.0.0.9250)
activeresource (2.1.1, 2.0.2)
activesupport (2.1.1, 2.0.2)
acts_as_tree (0.1.1)
archive-tar-minitar (0.5.2)
builder (2.1.2)
capistrano (2.5.0, 2.1.0)
capistrano-ext (1.2.1)
cgi_multipart_eof_fix (2.5.0)
chronic (0.10.2)
cmdparse (2.0.2)
color (1.4.0)
columnize (0.2)
dbd-odbc (0.2.4)
dbi (0.4.1)
deprecated (2.0.1)
exifr (0.10.9)
fastercsv (1.5.1)
fattr (2.2.0)
flexmock (0.9.0)
fxri (0.3.7, 0.3.6)
fxruby (1.6.16 x86-mswin32-60, 1.6.12 mswin32)
gem_plugin (0.2.3)
highline (1.4.0)
hoe (1.5.1)
i18n (0.6.9)
ldap (0.9.7 mswin32)
linecache (0.43 mswin32)
log4r (1.0.5)
minitest (4.7.5, 2.1.0)
mongrel (1.1.5 x86-mswin32-60, 1.1.2 mswin32)
mongrel_service (0.3.4 i386-mswin32)
multi_json (1.8.4)
mysql (2.7.3 mswin32)
needle (1.3.0)
net-scp (1.0.1)
net-sftp (2.0.1, 1.1.0)
net-ssh (2.0.4, 1.1.2)
net-ssh-gateway (1.0.0)
pdf-writer (1.1.8)
rails (2.1.1, 2.0.2)
rake (0.8.2, 0.8.1, 0.8.0, 0.7.3)
rcov (0.8.1.2.0 mswin32)
rio (0.4.1)
rmagick (2.0.0 mswin32)
ruby-breakpoint (0.5.1)
ruby-debug (0.10.2)
ruby-debug-base (0.10.2 mswin32)
ruby-net-ldap (0.0.4)
ruby-ntlm (0.0.1)
ruby-ole (1.2.11.1)
ruby-openid (2.1.2, 2.0.4)
rubyforge (0.4.4)
rubygems-update (1.4.0, 1.3.0, 1.2.0, 1.0.1)
rubyzip (0.9.4)
session (3.1.0)
sources (0.0.1)
spreadsheet (0.6.5.4)
sqlite3-ruby (1.2.1 mswin32)
to_excel (1.0)
to_xls (1.0.0)
transaction-simple (1.4.0)
tzinfo (0.3.38, 0.3.11)
wicked_pdf (0.7.2)
will_paginate (2.3.16, 2.3.12)
win32-api (1.2.2 x86-mswin32-60, 1.2.0 x86-mswin32-60, 1.0.4 mswin32)
win32-clipboard (0.4.4, 0.4.3)
win32-dir (0.3.2)
win32-eventlog (0.4.9, 0.4.6)
win32-file (0.5.5, 0.5.4)
win32-file-stat (1.3.1, 1.2.7)
win32-open3 (0.3.2 x86-mingw32)
win32-process (0.5.9, 0.5.3)
win32-sapi (0.1.4)
win32-service (0.6.1 x86-mswin32-60, 0.5.2 mswin32)
win32-sound (0.4.1)
windows-api (0.2.4, 0.2.0)
windows-pr (0.9.2, 0.7.2)
writeexcel (1.0.5)
xmpp4r (0.4)

C:\InstantRails\rails_apps>

Answer 1

I had this issue: 504 5.7.4 Unrecognized authentication type

when sent username and passwords parameters.

I think it depends on your MS Exchange server configuration. Resolved my config testing all combinations of the settings.

My setting is in config/environments/develop.rb:

# localhost because is in development
    config.action_mailer.default_url_options = { host: "127.0.0.1:3000" }
    config.active_support.deprecation = :notify
    config.action_mailer.delivery_method = :smtp
    config.action_mailer.smtp_settings = {

      :address =>              'mail.yourmailserver.com',
      :port =>                 25, # verify your port
      :domain =>               'yourmailserver.com',
      :openssl_verify_mode => 'none', # my server doesnt use openssl
      :enable_starttls_auto => false # i don't know why but it requires

    }

Hope it helps.