gistfile1.txt

#This file is smtp_tls.rb

require "openssl"
require "net/smtp"

Net::SMTP.class_eval do
  private
  def do_start(helodomain, user, secret, authtype)
    raise IOError, 'SMTP session already started' if @started
    check_auth_args(user, secret) if user || secret

    sock = timeout(@open_timeout) { TCPSocket.open(@address, @port) }
    @socket = Net::InternetMessageIO.new(sock)
    @socket.read_timeout = 60 #@read_timeout
    @socket.debug_output = STDERR #@debug_output

    check_response(critical { recv_response() })
    do_helo(helodomain)

    raise 'openssl library not installed' unless defined?(OpenSSL)
    starttls
    ssl = OpenSSL::SSL::SSLSocket.new(sock)
    ssl.sync_close = true
    ssl.connect
    @socket = Net::InternetMessageIO.new(ssl)
    @socket.read_timeout = 60 #@read_timeout
    @socket.debug_output = STDERR #@debug_output
    do_helo(helodomain)

    authenticate user, secret, authtype if user
    @started = true
  ensure
    unless @started
      # authentication failed, cancel connection.
        @socket.close if not @started and @socket and not @socket.closed?
      @socket = nil
    end
  end
 
  def do_helo(helodomain)
     begin
      if @esmtp
        ehlo helodomain
      else
        helo helodomain
      end
    rescue Net::ProtocolError
      if @esmtp
        @esmtp = false
        @error_occured = false
        retry
      end
      raise
    end
  end

  def starttls
    getok('STARTTLS')
  end
end


#this file is email.rb!
require 'mailfactory'
require 'smtp_tls'
class Email
  attr_accessor :to, :subject, :body

  def initialize(to,subject,body)
   @to = to
   @subject = subject
   @body = body
   self
  end

  def send_gmail
    username = 'lylesjt' #my Gmail user
    password = 'secret'
    mail = MailFactory.new
    mail.text = self.body
    mail.from = "someguy@ninjadeathsquad.com"
    mail.subject = self.subject
    mail.to = self.to

    Net::SMTP.start('smtp.gmail.com',587,"mail.backup.com",username,password,:plain) do |smtp|
      smtp.send_message(mail.to_s,mail.from,mail.to)
    end
  end
end

Then fire up irb, require 'email' and like so:
e = Email.new('guy@whatever.mil',"You'll like this...","Just kidding, you won't!!")
e.send_gmail

#All this silliness is necessary because google likes tls, and net/smtp doesn't do it out of the box