Disclaimer: I have not tried it myself and don't know for sure if it works...

There is a gem which might do that for you. Please add the following line to your Gemfile.local (create it if it does not exist yet). Then run bundle install to install the gem.

gem 'ruby-ntlm', :require => 'ntlm/smtp'

Now you can use

authentication: :ntlm

Thanks for the help, Holger.

I'm still unable to get mail delivery working, however. After enabling e-mail logging, this is what i get in my production log:

Processing AdminController#test_email (for XXX.XXX.XXX.XXX at 2012-04-09 11:23:48) [GET]
  Parameters: {"controller"=>"admin", "action"=>"test_email"}
Sending email notification to: 
Redirected to http://server:3000/settings/edit?tab=notifications
Completed in 9ms (DB: 0) | 302 Found [http://server/admin/test_email]

I'm including the configuration block I'm using below:

production:
  email_delivery:
    delivery_method: :smtp
    smtp_settings:
      address: "XXX.XXX.gov" 
      port: 25
      domain: 'XXX.gov'
      authentication: :ntlm
      user_name: "XXX\\XXXXXXXX" 
      password: "XXXXXX" 

Anything come to mind? As far as I can tell from the Settings page, Chili seems to believe that everything is configured properly, and yet I get none of the mailings.

Thanks,

Kirpal

This is probably a duplicate of #824 and #762: Make sure that your email settings (for the destination address/account) is unchecked for "I don't want to be notified of changes that I make myself."

...and that solved it. Thanks!