This project is archived and is in readonly mode.

#3289 ✓stale

tls not working with action mailer in Rails 2.3.3 with Ruby 1.9.1

Reported by metasoarous | September 28th, 2009 @ 02:02 AM

Hi - I have been trying to get action mailer to work with the restful_authentication plugin and a gmail account but have been unable to get past the following error

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

My understanding (after much checking) is that Rails 2.3.3 and Ruby 1.9.1 (any beyond 1.8.7) should have tls functionality built in and all that should be required to get it operating is to pass :enable_starttls_auto => true to the config.action_mailer.smtp_settings hash (although, checking the docs, it looks like true is the default, but everyone was throwing it in there, so I figured it couldn't hurt). This is not working for me though and I am wondering if anyone else has experienced either success or failure in this regard with these specific versions.

My settings are as follows -

config.action_mailer.delivery_method = :smtp config.action_mailer.smtp_settings = {

:address              => '',
:port                 => 587,    
:domain               => '',    
:user_name            => '',    
:password             => '**gmail-password**',
:authentication       => :plain,
:enable_starttls_auto => true


And the mailer code is pretty much exactly what got spit out by restful_authentication. The errors happen when I try to signup. So, once again, if others would share their experiences with tls on these versions of ruby and rails that would be greatly appreciated.

Comments and changes to this ticket

  • Dewayne Richardson

    Dewayne Richardson October 20th, 2009 @ 08:55 PM

    I also have tried the exact same above and am having the same issues with:

    ruby -v
    ruby 1.8.7 (2008-08-11 patchlevel 72) [i486-linux]

    Rails 2.3.3

  • Rizwan Reza

    Rizwan Reza May 15th, 2010 @ 05:25 PM

    • Tag changed from 1.9.1, 2.3.3, actionmailer, action_mailer, restful_authentication to 1.9.1, 2.3.3, actionmailer, action_mailer, bugmash, restful_authentication
  • Álvaro Gil

    Álvaro Gil May 15th, 2010 @ 07:10 PM

    I couldn't reproduce it on master using...

    ruby 1.8.7 (2009-06-12 patchlevel 174) [i686-darwin10.2.0], MBARI 0x6770, Ruby Enterprise Edition 2009.10

  • Curtis Carter

    Curtis Carter May 23rd, 2010 @ 04:36 AM

    I could not reproduce on 2.3.3 using:
    ruby 1.8.7 (2008-08-11 patchlevel 72) [i686-darwin10.3.0] OR
    ruby 1.9.1p378 (2010-01-10 revision 26273) [i386-darwin10.3.0]

    There are the known issues with < 1.8.7 since before 1.8.7 didn't support tls.

  • Rohit Arondekar

    Rohit Arondekar June 23rd, 2010 @ 03:35 AM

    • State changed from “new” to “stale”

    Closing ticket, if this is still an issue for somebody please make a comment to reopen the ticket and I'll oblige.

Create your profile

Help contribute to this project by taking a few moments to create your personal profile. Create your profile »

<h2 style="font-size: 14px">Tickets have moved to Github</h2>

The new ticket tracker is available at <a href=""></a>