A solution for: An error occurred while sending mail (SSL_connect returned=1 errno=0 state=unknown state: unknown protocol) in Redmine 2.0 / Rails 3.2.3

29 May · by Tim Kamanin · 2 min read

Being a Drupal developer I do use magnificent redmine (http://redmine.org) to manage my tasks and projects. If you don't know, Redmine is a Rails-based application so from time to time I have my hands dirty with ruby code (it doesn't hurt at all ;)).

Today I decided to upgrade our internal redmine installation from version 1.4 to 2.0. The upgrade process went very smooth, but in the end I encountered a problem with mail sending. Every attempt to send an email from redmine installation led to the error message: An error occurred while sending mail (SSL_connect returned=1 errno=0 state=unknown state: unknown protocol). I use Google Apps SMTP servers for mail, so my configuration file looked something like this:

production:
  email_delivery:
delivery_method: :smtp
smtp_settings:
  tls: true
  enable_starttls_auto: true
  address: "smtp.gmail.com"
  port: 587
  domain: "smtp.gmail.com" # 'your.domain.com' for GoogleApps
  authentication: :plain
  user_name: "your_email@gmail.com"
  password: "your_password"

With redmine 1.4 these settings worked just fine, but redmine 2.0 made a major jump from Rails 2.3.x to rails 3.2.x and, as it usually happens in the Rails world, something has changed in the internals. In the end it turned out that you can't have both _tls: true_ and _ _ _enable_starttls_auto: true _in your settings, so you need to comment tls: true setting and your redmine will be able to send email messages via Google's SMTP. Hope this will be helpful to someone.

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Igor Machado

Thanks a lot!! Saved me hours of pain :)

Reply · 1 year, 3 months ago
zam

Great, it finally works for me too!

Reply · 5 years, 5 months ago
Sundar Babu

This helped me at least 2-3 hours of agony! Thank you so much.

Reply · 5 years, 5 months ago