Sending and receiving Outlook email via Ruby

(disclaimer: this worked for my corporate Outlook web email account. I don’t know if it will work for all. I’m posting this just in case it helps somebody else.)

I recently had a need to detect changes in one application and send them to another application. Ideally, I was looking for “connector” or “glue” software between the two applications, but none existed. So, I needed to write my own.

The first application did not have any callback methods to notify when changes occurred, but it did have a mechanism that could send email whenever a change happened. The second application had an email receiver that could accept updates whenever it received plain-text, CSV formatted emails containing relevant fields. All I needed to do to write this “connector” software was setup a cron job that reads incoming mail from the first application, parse what changed, reformat it, and then send it to the other application.

Using Ruby, I found Mikel Lindsaar’s excellent mail library. His README.md page and github pages gave the following examples for MobileMe and GMail type email accounts:

# Sending via MobileMe
Mail.defaults do
  delivery_method :smtp, { :address              => 'smtp.me.com',
                           :port                 => 587,
                           :domain               => 'your.host.name',
                           :user_name            => '',
                           :password             => '',
                           :authentication       => 'plain',
                           :enable_starttls_auto => true  }
end

#Sending via GMail
Mail.defaults do
  delivery_method :smtp, { :address              => 'smtp.gmail.com',
                           :port                 => 587,
                           :domain               => 'your.host.name',
                           :user_name            => '',
                           :password             => '',
                           :authentication       => 'plain',
                           :enable_starttls_auto => true  }
end

That’s great. I was able to test the library using a GMail account, but my company was using Office 365 or Outlook.com. What were the correct parameters for that?? After a couple days of Googling, telnetting, and trial-and-error, I finally figured it out.

Here is what you need to do:

Step 1:
Log into your Outlook web account. Follow the 3 steps at this link to find the correct POP3 and SMTP addresses for your account: “Settings for POP and IMAP access“

My address looked like “podxxxxx.outlook.com” where xxxxx is some magic Microsoft number.

Step 2:
Plug your address, username, and password into the Mail.defaults configuration:

Mail.defaults do
  delivery_method :smtp, { 
                           :address              => 'xxxxxxx.outlook.com',
                           :port                 => 587,
                           :domain               => 'example.com',
                           :user_name            => 'youremailaddress@example.com',
                           :password             => 'yourpassword',
                           :authentication       => :login,
                            :enable_starttls_auto => true  
                           }

  retriever_method :pop3, { :address    => 'xxxxxxx.outlook.com',
                          :port       => 995,
                          :user_name  => 'youremailaddress@example.com',
                          :password   => 'yourpassword',
                          :enable_ssl => true    }
end

That’s it! You’re then set to send and receive Outlook email. IMAP4 also works, if you prefer that. (And obviously, you shouldn’t hard-code your username and password, but this should be enough to make sure you can send & receive email.)

So beyond configuration, here is a basic example script showing how to send and receive Outlook email via Ruby.

Good luck!

require 'mail'  # ruby mail library. https://github.com/mikel/mail

# configure delivery and retrieval methods
Mail.defaults do
  delivery_method :smtp, { 
                           :address              => 'xxxxxxx.outlook.com',
                           :port                 => 587,
                           :domain               => 'example.com',
                           :user_name            => 'youremailaddress@example.com',
                           :password             => 'yourpassword',
                           :authentication       => :login,
                            :enable_starttls_auto => true  
                           }

  retriever_method :pop3, { :address    => 'xxxxxxx.outlook.com',
                          :port       => 995,
                          :user_name  => 'youremailaddress@example.com',
                          :password   => 'yourpassword',
                          :enable_ssl => true    }
end

# retrieve first 5 messages
emails = Mail.find(:what => :first, :count => 5)

# or retrieve and delete from server first 5 emails
#emails = Mail.find_and_delete(:what => :first, :count => 5)

puts "Number of emails retrieved: #{emails.length}"

# loop thru all emails and print content
emails.each do |email|

    # email fields defined at https://github.com/mikel/mail/tree/master/lib/mail/fields
    puts "from     : " + email.from.to_s       #=> 'fromname@example.com'
    puts "to       : " + email.to.to_s         #=> 'toname@example.com'
    puts "cc       : " + email.cc.to_s         #=> 'ccname@example.com'
    puts "bcc      : " + email.bcc.to_s        #=> 'bccname@example.com'    
    
    puts "subject  : " + email.subject         #=> "This is the subject"
    puts "date     : " + email.date.to_s       #=> '26 Nov 2013 10:00:00 -0800'
    puts "messageid: " + email.message_id      #=> '<ABCD1234.12345678@xxx.xxx>'
    puts "body     : " + email.body.decoded    #=> 'This is the body of the email...    

end

# send test message
Mail.deliver do

    from    'youremailaddress@example.com'
    to      'someaddress@example.com'
    subject 'test subject'
    body    'test body'

end