Ruby 1.8.7 + Rails 2.3.2 + TLS = Where's the documentation?

After spending a few hours reading dozens of blogs and tutorials I am still stumped. Numerous sites mention ruby 1.8.7 and rails 2.3 supporting TLS out of the box. However, I can not find any documentation on setting this up to send emails correctly. Furthermore, after attempting to send emails using Gmail and TLS i get the following error:

530 5.7.0 Must issue a STARTTLS command first. i6sm501424tid.20

/usr/local/lib/ruby/1.8/net/smtp.rb:942:in `check_auth_response' /usr/local/lib/ruby/1.8/net/smtp.rb:733:in `auth_plain' /usr/local/lib/ruby/1.8/net/smtp.rb:725:in `send' /usr/local/lib/ruby/1.8/net/smtp.rb:725:in `authenticate' /usr/local/lib/ruby/1.8/net/smtp.rb:566:in `do_start' /usr/local/lib/ruby/1.8/net/smtp.rb:525:in `start'

Can anyone point me in the right direction?!

Thanks in advance!

I have the following configuration in my config/environments/development.rb: # Don't care if the mailer can't send config.action_mailer.raise_delivery_errors = true

# set delivery method to :smtp, :sendmail or :test config.action_mailer.delivery_method = :smtp

# these options are only needed if you choose smtp delivery config.action_mailer.smtp_settings = {   :address => 'smtp.gmail.com',   :enable_starttls_auto => true,   :port => 587,   :domain => 'digiaid.com.au',   :authentication => :login,   :user_name => 'info@digiaid.com.au',   :password => 'secret' }

Looks like you have a :user_name misspecified, this is meant to be the gmail user account that will be used to send the email and must be a valid gmail account.

Here's what I use as: config/initializers/action_mailer.rb:

ActionMailer::Base.delivery_method = :smtp

ActionMailer::Base.smtp_settings = {    :enable_starttls_auto => true,    :address => "smtp.gmail.com",    :port => "587",    :domain => "engine.local",    :authentication => :plain,    :user_name => "bultaco.rick",    :password => "*************" }

I've tried your method - config.... in config/environments/ development.rb works as well.

ActionMailer::Base in actionmailer-2.3.2/rdoc has a section on configuration options.

Rick wrote:

Looks like you have a :user_name misspecified, this is meant to be the gmail user account that will be used to send the email and must be a valid gmail account.

Very strange... Now I am getting the error: Net::SMTPAuthenticationError (535-5.7.1 Username and Password not accepted

I have tried changing the value of :user_name to 'info' as well, same error...

I'm not sure what you mean by "changing the value of :user_name to 'info'..." but here's the deal.

Whatever you use as the value associated with :user_name I should be able to sent it mail at gmail. For instance, if you say...

:user_name => "monkeylips"

I should be able to send an email (with attached banana) to monkeylips@gmail.com

Got it?

I'm not sure what you mean by "changing the value of :user_name to 'info'..." but here's the deal.

Whatever you use as the value associated with :user_name I should be able to sent it mail at gmail. For instance, if you say...

:user_name => "monkeylips"

I should be able to send an email (with attached banana) to monkeylips@gmail.com

Got it?

# these options are only needed if you choose smtp delivery config.action_mailer.smtp_settings = {   :address => 'smtp.gmail.com',   :enable_starttls_auto => true,   :port => 587,   :domain => '...',   :authentication => :login,   :user_name => '...',   :password => 'secret' }

Correct configuration to get this working is: config.action_mailer.smtp_settings = {     :enable_starttls_auto => true,     :address => 'smtp.gmail.com',     :port => 587,     :domain => 'your.domain.com',     :authentication => :plain,     :user_name => 'name@your.domain.com',     :password => 'password' }