environment.rb

#
# Add this to the bottom of environment.rb
#

require 'smtp_tls' 

ActionMailer::Base.delivery_method = :smtp
ActionMailer::Base.raise_delivery_errors = true

ActionMailer::Base.smtp_settings = {
  :tls => true,
  :address => "smtp.gmail.com" ,
  :port => 587,
  :domain => "mydomain.com" ,
  :authentication => :plain,
  :user_name => "[email protected]" ,
  :password => "mypassword" ,
}

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, authtype if user or secret
   
    sock = timeout(@open_timeout) { TCPSocket.open(@address, @port) }
    @socket = Net::InternetMessageIO.new(sock)
    @socket.read_timeout = 60 #@read_timeout
   
    check_response(critical { recv_response() })
    do_helo(helodomain)
   
    if starttls
      raise 'openssl library not installed' unless defined?(OpenSSL)
      ssl = OpenSSL::SSL::SSLSocket.new(sock)
      ssl.sync_close = true
      ssl.connect
      @socket = Net::InternetMessageIO.new(ssl)
      @socket.read_timeout = 60 #@read_timeout
      do_helo(helodomain)
    end
   
    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') rescue return false
    return true
  end
 
  def quit
    begin
      getok('QUIT')
      rescue EOFError
    end
  end
end