So I don’t why I always have trouble setting up web apps to send mail through my hosted GMail accounts (like, um, Redmine?). Really, it seems like I end up pulling my hair out every time I have to do it.

So the problem we want to solve today should be straightforward. I have a Ruby-on-Rails app called Redmine which I want to have send notifications and whatnot via my Google Apps hosted GMail account. So here’s some basic instruction from Redmine. Great. And here is my email.yml file that actually works (passwords and other crap redacted, obviously):

production:
  delivery_method: :smtp
  smtp_settings:
    tls: true
    address: "smtp.gmail.com"
    port: 587
    domain: "example.com"
    authentication: :plain
    user_name: "robots@example.com"
    password: N1ceP@55wurd!

This set-up will allow Redmine to send emails from robots@example.com using hosted GMail