Ruby, RoR, gmail and NET::SMTP

Question

Is there any way to use gmail as a smtp server on rails 2.3.5/ruby 1.9.1?

My smtp settings for actionmailer are

options = {
  :address              => "smtp.gmail.com",
  :port                 => 587,
  :domain               => 'REMOVED',
  :user_name            => 'REMOVED',
  :password             => 'REMOVED',
  :authentication       => 'plain',
  :enable_starttls_auto => true  }

and these result in the error

Net::SMTPAuthenticationError: 530 5.7.0 Must issue a STARTTLS command first. 

Answer 1

Try this:

#config/initializers/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

    if RUBY_VERSION == "1.8.6"
      check_auth_args user, secret, authtype if user or secret
    else
      check_auth_args user, secret if user or secret
    end

    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

  def quit
    begin
      getok('QUIT')
    rescue EOFError
    end
  end