# http://www.jamesbritt.com/2007/12/18/sending-mail-through-gmail-with-ruby-s-net-smtp
# http://d.hatena.ne.jp/zorio/20060416
 
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, authtype if user or 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
 
# http://snippets.dzone.com/posts/show/2362
 
def send_email(from, from_alias, to, to_alias, subject, message)
  msg = <<END_OF_MESSAGE
From: #{from_alias} <#{from}>
To: #{to_alias} <#{to}>
Subject: #{subject}
 
#{message}
END_OF_MESSAGE
 
  Net::SMTP.start("smtp.gmail.com",
                  587,
                  "localhost.localdomain",
                  your_username,
                  your_password,
                  "plain") do |smtp|
    smtp.send_message msg, from, to
  end
end
 
send_email("gilesb@gmail.com",
           "Giles Bowkett",
           "giles@entp.com",
           "G Money Bowkett",
           "cause I'm an ace when I face the bass",
           "forty-side is the place that is giving me grace")