Ruby, RoR, gmail and NET::SMTP - ruby-on-rails

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