Thanks for a swift reply Andrea.

I know that server_settings was renamed to smtp_settings with rails 2.

Aha! With this in my environment.rb:

config.action_mailer.smtp_settings = {
   :address => "smtp.gmail.com"
   :port => 587,
   :domain => "westportbookfestival.org",
   :authentication => :plain,
   :user_name => "user",
   :password => "pass"
  }

I can start radiant again. :-)

Now I get a different error when I attempt to send a test email:

Net::SMTPUnknownError (530 5.7.0 Must issue a STARTTLS command first. z37sm3359725ikz.6
):
/System/Library/Frameworks/Ruby.framework/Versions/1.8/usr/lib/ ruby/1.8/net/smtp.rb:680:in `check_response' /System/Library/Frameworks/Ruby.framework/Versions/1.8/usr/lib/ ruby/1.8/net/smtp.rb:582:in `auth_login' /System/Library/Frameworks/Ruby.framework/Versions/1.8/usr/lib/ ruby/1.8/net/smtp.rb:686:in `critical' /System/Library/Frameworks/Ruby.framework/Versions/1.8/usr/lib/ ruby/1.8/net/smtp.rb:581:in `auth_login' /System/Library/Frameworks/Ruby.framework/Versions/1.8/usr/lib/ ruby/1.8/net/smtp.rb:571:in `__send__' /System/Library/Frameworks/Ruby.framework/Versions/1.8/usr/lib/ ruby/1.8/net/smtp.rb:571:in `authenticate' /System/Library/Frameworks/Ruby.framework/Versions/1.8/usr/lib/ ruby/1.8/net/smtp.rb:411:in `do_start' /System/Library/Frameworks/Ruby.framework/Versions/1.8/usr/lib/ ruby/1.8/net/smtp.rb:378:in `start' /System/Library/Frameworks/Ruby.framework/Versions/1.8/usr/lib/ ruby/1.8/net/smtp.rb:316:in `start' /Library/Ruby/Gems/1.8/gems/radiant-0.6.7/vendor/rails/ actionmailer/lib/action_mailer/base.rb:586:in `perform_delivery_smtp' /Library/Ruby/Gems/1.8/gems/radiant-0.6.7/vendor/rails/ actionmailer/lib/action_mailer/base.rb:469:in `__send__' /Library/Ruby/Gems/1.8/gems/radiant-0.6.7/vendor/rails/ actionmailer/lib/action_mailer/base.rb:469:in `deliver!' /Library/Ruby/Gems/1.8/gems/radiant-0.6.7/vendor/rails/ actionmailer/lib/action_mailer/base.rb:383:in `deliver' /vendor/extensions/newsletter/app/controllers/ newsletters_controller.rb:59:in `send_test_email' /vendor/extensions/newsletter/app/controllers/ newsletters_controller.rb:13:in `create' /Library/Ruby/Gems/1.8/gems/radiant-0.6.7/vendor/rails/actionpack/ lib/action_controller/base.rb:1158:in `send' /Library/Ruby/Gems/1.8/gems/radiant-0.6.7/vendor/rails/actionpack/ lib/action_controller/base.rb:1158:in `perform_action_without_filters'
...

I tried using a simpler configuration:

  config.action_mailer.smtp_settings = {
     :address => "mail.atlantisbooks.org",
     :port => 25,
     :domain => "atlantisbooks.org"
    }

which actually worked!

So I suppose the problem could be related to gmail requiring an SSL SMTP connection. Has anyone had any success making the action_mailer work with gmail's hosted webmail service?

Googling turned up this:
        
http://www.stephenchu.com/2006/06/how-to-use-gmail-smtp-server-to-send.html

Although it is quite old, so I don't know if the article is relevant anymore.

Thanks again,
Drew
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