Why doesn't Delayed Jobs work with my ActionMailer production setup?

Question

I am working on a Ruby (1.8.6) on Rails (2.3.5) application in which I am currently using Gmail to deliver email messages. I want to switch to sending the messages with Delayed Jobs.

I have delayed jobs sending messages on my development environment but when I deploy to my production server and try the messages get rejected and an error shows up in my delayed_jobs table: 530 5.7.0 Must issue a STARTTLS command first. i25sm12946175anh.17. 530 5.7.0 Must issue a STARTTLS command first. i25sm12946175anh.17. I've seen this error before (when I don't have TLS enabled in my config). But it was working before I started using delayed_jobs. Here is my mail config:

ActionMailer::Base.smtp_settings = {
  :enable_starttls_auto => true,
  :address => 'smtp.gmail.com',
  :port => 587,
  :domain => 'example.com',
  :authentication => :plain,
  :user_name => 'user@example.com',
  :password => 'password'
}

Any help with this issue is greatly appreciated.

Update : The application is actually running on REE ruby 1.8.7. So maybe delayed jobs is somehow using the regular ruby interpreter installed on the server (1.8.6). But, how do I get delayed jobs to use my REE install? And how do I tell what things are using what version of Ruby.

Answer 1

Normally you would use :enable_starttls_auto as you wrote, but that only works for ruby >= 1.8.7 and ruby >= 1.9.

So you need to use the solution as stated here : define a file smtp_tls.rb which you place in your initializers folder.

Answer 2

But, how do I get delayed jobs to use my REE install? And how do I tell what things are using what version of Ruby.

The script/delayed_job command uses the system Ruby. So " which ruby " should point to the REE installation. If not, you can force it by using the Ruby executable. Lets say, your REE is installed at /opt/ruby-enterprise-1.8.7-2010.01 . Then:

$ RAILS_ENV=production /opt/ruby-enterprise-1.8.7-2010.01/bin/ruby script/delayed_job -n 2 start

Or if you use the rake command to start, like:

$ rake jobs:work -t RAILS_ENV=production

Then which rake should point to your REE installation. If its not, then you can make it use REE by:

RAILS_ENV=production /opt/ruby-enterprise-1.8.7-2010.01/bin/rake jobs:work -t