# Ruby 1.8.7 + Rails 2.3.2 + TLS = Where's the documentation? **URL:** \ **Category:** Rails\ **Created:** [April 13, 2009, 4:01pm UTC](https://www.ruby-forum.com/t/ruby-1-8-7-rails-2-3-2-tls-wheres-the-documentation/165389 "2009-04-13T16:01:47Z")\ **Posts on this page:** 6\ **Page:** 1
**Author:** ![dmht81](https://www.ruby-forum.com/letter_avatar_proxy/v4/letter/d/57b2e6/32.png) [@dmht81](https://www.ruby-forum.com/u/dmht81)\ **Post date:** [April 13, 2009, 4:01pm UTC](https://www.ruby-forum.com/t/ruby-1-8-7-rails-2-3-2-tls-wheres-the-documentation/165389/1 "2009-04-13T16:01:47Z")
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](http://smtp.gmail.com)’, :enable\_starttls\_auto =\> true, :port =\> 587, :domain =\> ‘…’, :authentication =\> :login, :user\_name =\> ‘…’, :password =\> ‘secret’ } ---
**Author:** ![dmht81](https://www.ruby-forum.com/letter_avatar_proxy/v4/letter/d/57b2e6/32.png) [@dmht81](https://www.ruby-forum.com/u/dmht81)\ **Post date:** [April 13, 2009, 10:11pm UTC](https://www.ruby-forum.com/t/ruby-1-8-7-rails-2-3-2-tls-wheres-the-documentation/165389/2 "2009-04-13T22:11:13Z")
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](http://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. On Apr 13, 4:01 am, obiwan chinobi [removed\_email\_address@domain.invalid](mailto:removed_email_address@domain.invalid) ---
**Author:** ![dmht81](https://www.ruby-forum.com/letter_avatar_proxy/v4/letter/d/57b2e6/32.png) [@dmht81](https://www.ruby-forum.com/u/dmht81)\ **Post date:** [April 13, 2009, 11:10pm UTC](https://www.ruby-forum.com/t/ruby-1-8-7-rails-2-3-2-tls-wheres-the-documentation/165389/3 "2009-04-13T23:10:25Z")
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… ---
**Author:** ![dmht81](https://www.ruby-forum.com/letter_avatar_proxy/v4/letter/d/57b2e6/32.png) [@dmht81](https://www.ruby-forum.com/u/dmht81)\ **Post date:** [April 14, 2009, 3:25am UTC](https://www.ruby-forum.com/t/ruby-1-8-7-rails-2-3-2-tls-wheres-the-documentation/165389/4 "2009-04-14T03:25:28Z")
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 removed\_email\_address@domain.invalid Got it? On Apr 13, 11:10 am, obiwan chinobi [removed\_email\_address@domain.invalid](mailto:removed_email_address@domain.invalid) ---
**Author:** ![dmht81](https://www.ruby-forum.com/letter_avatar_proxy/v4/letter/d/57b2e6/32.png) [@dmht81](https://www.ruby-forum.com/u/dmht81)\ **Post date:** [April 14, 2009, 3:25am UTC](https://www.ruby-forum.com/t/ruby-1-8-7-rails-2-3-2-tls-wheres-the-documentation/165389/5 "2009-04-14T03:25:26Z")
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 removed\_email\_address@domain.invalid Got it? On Apr 13, 11:10 am, obiwan chinobi [removed\_email\_address@domain.invalid](mailto:removed_email_address@domain.invalid) ---
**Author:** ![dmht81](https://www.ruby-forum.com/letter_avatar_proxy/v4/letter/d/57b2e6/32.png) [@dmht81](https://www.ruby-forum.com/u/dmht81)\ **Post date:** [April 14, 2009, 4:25pm UTC](https://www.ruby-forum.com/t/ruby-1-8-7-rails-2-3-2-tls-wheres-the-documentation/165389/6 "2009-04-14T16:25:54Z")
> # these options are only needed if you choose smtp delivery > > config.action\_mailer.smtp\_settings = { > :address =\> ‘[smtp.gmail.com](http://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](http://smtp.gmail.com)’, :port =\> 587, :domain =\> ‘[your.domain.com](http://your.domain.com)’, :authentication =\> :plain, :user\_name =\> ‘removed\_email\_address@domain.invalid’, :password =\> ‘password’ }