A simple ruby script that uses pony.rb to mass mail a list of contacts specified in json format.

ponymailer

#
# Note that this program does not have any error-handling code, so if it fails, 
# you will just get some error messages at the command line. It won't skip the offending
# email and move on with the task; it will fail entirely.
#
# Keep an eye on the command prompt periodically, if you don't
# know how to write error-handling code. If it does fail, as it occassionally will
# due to a server rejecting the email, or something like that, then look in your
# Gmail 'sent' folder to identify the last email sent. Then, compare to the list
# of contacts. It will almost certainly have failed because of the next email in the list.
# In that case, delete all emails before the offending email in your contacts list variable, and 
# run the program again. This is a crude solution, admittedly, but I haven't finished 
# coding the error-handling part of the script. 
#
# To test this script as is, assign your Gmail username to the username variable,
# your Gmail password to the password variable. Then, add your email and name,
# a couple of times to the email list (contacts variable) substituting your email for the email 
# string and your name for the name string. To avoid throwing an error, add
# an attachment too by specifying the path to the file. To keep it easy, save
# this file (ponymailer.rb) to the same directory as the attachment, and just give the 
# name of the file and ponymailer will understand that you mean the current directory.
# Then, run this file from the command line with the following command:
# ruby ponymailer.rb

require 'pony'

# mail service username (gmail, for now)
username = 'someusername'

# mail service password (gmail, for now) 
password = 'somepassword'

# smtp address and port number (gmail for now)
smtpaddress = 'smtp.gmail.com'

# make sure this is a string
port = '587'

# to...list of contacts, in json format

contacts = 
[

  # contact list should take the following form (excluding the # of course):
  
  # ['contact0@email.com', 'Dr. Contact0'],
  # ['contact0@email.com', 'Dr. Contact0'],
  # ['contact0@email.com', 'Dr. Contact0'],
  # ['contact3@email.com', 'Dr. Contact3'],
  # ['contactn@email.com', 'Dr. Contactn']

]


# name of sender
from = "Ms. Some Sender"

# subject of email
subject = "Some Subject"

# body of email specified as a string
body = "The body of the email should proceed from the line beneath the salutation,\n
        and newlines should be indicated using: \n. Other standard ruby formatting\n
        rules apply. Please send some test emails to accounts you control first,
        so that you can make sure the formatting looks reasonable. "

# name and path of attachment
attachment = "path/to/file.format"

# mailing loop
contacts.each do |contact|
  
  # Create new Mersenne Twister based pseudo-random number generator with seed - 
  # this will be used later to generate a random number of seconds for the script 
  # to sleep between emails
  rander = Random.new(1234)

  Pony.mail({
    :to =>  contact[0],
    # make sure the from field matches the email sender - see :user_name and :password below
    :from => from,
    :subject => subject,
    :body => "Dear " + contact[1] + ",\n\n" + body,
    :attachments => {attachment => File.binread(attachment)},
    :via => :smtp,
    :via_options => {
      :address              => smtpaddress,
      :port                 => port,
      :enable_starttls_auto => true,
      :user_name            => username,
      :password             => password,
      :authentication       => :plain, # :plain, :login, :cram_md5, no auth by default
      :domain               => "localhost.localdomain", # the HELO domain provided by the client to the server
      
    }
  })

  # Sleep the program execution for a random number of seconds between 1 and n, 
  # to give some semblance of human-like behavior
  sleep(rander.rand(1..74))

end

This works. I am now finding a way to attach depending on the test running