Rails 3, ActionMailer, and Google Apps for Domains
After upgrading my Redmine installation to Redmine 2 (the development branch) emails stopped being delivered.
I send emails through Google Apps for Domains, so I had the following in my configuration.yml (previously email.yml):
delivery_method: :smtp smtp_settings: address: "smtp.gmail.com" port: 587 domain: "substancelab.com" authentication: "login" user_name: "firstname.lastname@example.org" password: "passw0rd" tls: true
I am pretty sure it used to work before the upgrade, now; not so much.
Damn you, SSL
Alas, when I ran
rake redmine:email:test I kept getting a
An error occurred while sending mail (SSL_connect returned=1 errno=0 state=SSLv2/v3 read server hello A: unknown protocol)
What is TLS even?
I knew this has something to do with the TLS settings, but Google didn't reveal any concrete, working advice. Adding
enable_starttls_auto: true, which seems to be most prevalent solution didn't change anything for me.
One or the other, but not both
tls: true in the settings was messing things up even if
starttls_auto is enabled. Changing my settings to
delivery_method: :smtp smtp_settings: address: smtp.gmail.com port: 587 domain: substancelab.com authentication: login user_name: "email@example.com" password: passw0rd enable_starttls_auto: true
made my email delivery work again.
File this under "blogged so you don't have to suffer as I did".