Redmine : send mail via gmail error SSL_connect or STARTTLS - ruby-on-rails

Question

i try to configure redmine for email notifications
So my configuration in configuration.yml is :
production:
email_delivery:
delivery_method: :smtp
smtp_settings:
enable_starttls_auto: true
address: "smtp.gmail.com"
port: '587'
domain: "smtp.gmail.com"
authentication: :plain
user_name: "mymail#gmail.com"
password: "mypass"
According to this tutorial :
http://www.redmine.org/projects/redmine/wiki/EmailConfiguration#Simple-Login-Authentication-default-settings
But when i try : Send a test mail, i have this error :
An error occurred while sending mail (530 5.7.0 Must issue a STARTTLS command first. n7sm25368265eef.5 - gsmtp )
If i have :
production:
email_delivery:
delivery_method: :smtp
smtp_settings:
tls: true
enable_starttls_auto: true
address: "smtp.gmail.com"
port: '587'
domain: "smtp.gmail.com"
authentication: :plain
user_name: "mymail#gmail.com"
password: "mypass"
I have this error :
An error occurred while sending mail (SSL_connect returned=1 errno=0 state=unknown state: unknown protocol)
Any ideas ? Redmine version : 2.0.1, Ruby : 1.9.3

Answer 1

1.Save the following code within your rails app in lib/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
##socket.debug_output = STDERR ##debug_output
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
##socket.debug_output = STDERR ##debug_output
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, OpenSSL::SSL::SSLError
end
end
end
2.Add this code to config/environment.rb (after everything else):
require “smtp_tls”
ActionMailer::Base.smtp_settings = {
:address => “smtp.gmail.com”,
:port => 587,
:authentication => :plain,
:user_name => “someone#openrain.com”,
:password => ’someonesPassword’
}
3.Use ActionMailer as normal.