chrisroos/2018-04-30-rails-and-aws-ses.md

Testing Rails ActionMailer and AWS SES

I added two verified email addresses to AWS SES so that I could send emails from/to them while in the SES Sandbox.

UserMailer

class UserMailer < ApplicationMailer
  default from: 'accounts+aws-ses@gofreerange.com'

  def welcome_email
    mail(to: 'chris.roos@gofreerange.com', subject: 'Welcome to My Awesome Site')
  end
end

ActionMailer config

config.action_mailer.smtp_settings = {
  address: 'email-smtp.eu-west-1.amazonaws.com',
  port:	25, # or 465 or 587
  enable_starttls_auto: <boolean>,
  tls: <boolean>, 
  ssl: <boolean>, 
  user_name: '<username>',
  password: '<password>'
}

Test command

$ rails r "UserMailer.with({}).welcome_email.deliver_now"

Results

In summary:

Ports 25 and 587 require enable_starttls_auto to be set to true, and for tls and ssl to be set to false.

Port 465 ignores enable_starttls_auto and requires either tls or ssl to be set to true.

Port	Enable StartTLS Auto	TLS	SSL	Outcome
25	True	True	True	`OpenSSL::SSL::SSLError: SSL_connect returned=1 errno=0 state=SSLv2/v3 read server hello A: unknown protocol`
25	True	True	False	`OpenSSL::SSL::SSLError: SSL_connect returned=1 errno=0 state=SSLv2/v3 read server hello A: unknown protocol`
25	True	False	True	`OpenSSL::SSL::SSLError: SSL_connect returned=1 errno=0 state=SSLv2/v3 read server hello A: unknown protocol`
25	True	False	False	Email sent correctly
25	False	False	False	`Net::SMTPAuthenticationError: 530 Must issue a STARTTLS command first`
25	False	True	True	`OpenSSL::SSL::SSLError: SSL_connect returned=1 errno=0 state=SSLv2/v3 read server hello A: unknown protocol`
25	False	True	False	`OpenSSL::SSL::SSLError: SSL_connect returned=1 errno=0 state=SSLv2/v3 read server hello A: unknown protocol`
25	False	False	True	`OpenSSL::SSL::SSLError: SSL_connect returned=1 errno=0 state=SSLv2/v3 read server hello A: unknown protocol`
465	True	True	True	Email sent correctly
465	True	True	False	Email sent correctly
465	True	False	True	Email sent correctly
465	True	False	False	`Net::ReadTimeout: Net::ReadTimeout`
465	False	False	False	`Net::ReadTimeout: Net::ReadTimeout`
465	False	True	True	Email sent correctly
465	False	True	False	Email sent correctly
465	False	False	True	Email sent correctly
587	True	True	True	`OpenSSL::SSL::SSLError: SSL_connect returned=1 errno=0 state=SSLv2/v3 read server hello A: unknown protocol`
587	True	True	False	`OpenSSL::SSL::SSLError: SSL_connect returned=1 errno=0 state=SSLv2/v3 read server hello A: unknown protocol`
587	True	False	True	`OpenSSL::SSL::SSLError: SSL_connect returned=1 errno=0 state=SSLv2/v3 read server hello A: unknown protocol`
587	True	False	False	Email sent correctly
587	False	False	False	`Net::SMTPAuthenticationError: 530 Must issue a STARTTLS command first`
587	False	True	True	`OpenSSL::SSL::SSLError: SSL_connect returned=1 errno=0 state=SSLv2/v3 read server hello A: unknown protocol`
587	False	True	False	`OpenSSL::SSL::SSLError: SSL_connect returned=1 errno=0 state=SSLv2/v3 read server hello A: unknown protocol`
587	False	False	True	`OpenSSL::SSL::SSLError: SSL_connect returned=1 errno=0 state=SSLv2/v3 read server hello A: unknown protocol`