Monkey-patch enabling Rails 3.0 - 3.1 to use SMTP over SSL

gistfile1.rb

# config/initializers/email.rb


require 'mail'

# Monkey-patch Mail to support SSL, which Fastmail mandates by 30 June 2012.
#
# Mail introduced SSL support in v2.4.0.
# Rails / ActionMailer doesn't use that version of Mail until Rails 3.2.0.
#
# The code below is copied from Mail v2.4.4.
#
# TODO: remove this monkey-patch once we're on Rails >= 3.2.0.
module Mail
  class SMTP
    # Send the message via SMTP.
    # The from and to attributes are optional. If not set, they are retrieve from the Message.
    def deliver!(mail)

      # Set the envelope from to be either the return-path, the sender or the first from address
      envelope_from = mail.return_path || mail.sender || mail.from_addrs.first
      if envelope_from.blank?
        raise ArgumentError.new('A sender (Return-Path, Sender or From) required to send a message')
      end

      destinations ||= mail.destinations if mail.respond_to?(:destinations) && mail.destinations
      if destinations.blank?
        raise ArgumentError.new('At least one recipient (To, Cc or Bcc) is required to send a message')
      end

      message ||= mail.encoded if mail.respond_to?(:encoded)
      if message.blank?
        raise ArgumentError.new('A encoded content is required to send a message')
      end

      smtp = Net::SMTP.new(settings[:address], settings[:port])
      if settings[:tls] || settings[:ssl]
        if smtp.respond_to?(:enable_tls)
          unless settings[:openssl_verify_mode]
            smtp.enable_tls
          else
            openssl_verify_mode = settings[:openssl_verify_mode]
            if openssl_verify_mode.kind_of?(String)
              openssl_verify_mode = "OpenSSL::SSL::VERIFY_#{openssl_verify_mode.upcase}".constantize
            end
            context = Net::SMTP.default_ssl_context
            context.verify_mode = openssl_verify_mode
            smtp.enable_tls(context)
          end
        end
      elsif settings[:enable_starttls_auto]
        if smtp.respond_to?(:enable_starttls_auto)
          unless settings[:openssl_verify_mode]
            smtp.enable_starttls_auto
          else
            openssl_verify_mode = settings[:openssl_verify_mode]
            if openssl_verify_mode.kind_of?(String)
              openssl_verify_mode = "OpenSSL::SSL::VERIFY_#{openssl_verify_mode.upcase}".constantize
            end
            context = Net::SMTP.default_ssl_context
            context.verify_mode = openssl_verify_mode
            smtp.enable_starttls_auto(context)
          end
        end
      end

      response = nil
      smtp.start(settings[:domain], settings[:user_name], settings[:password], settings[:authentication]) do |smtp_obj|
        response = smtp_obj.sendmail(message, envelope_from, destinations)
      end

      return settings[:return_response] ? response : self
    end
  end
end



ActionMailer::Base.smtp_settings = {
  address:              'mail.messagingengine.com',
  port:                 465,
  domain:               'yourdomain.com',
  user_name:            'your_username',
  password:             'xxxxxxx',
  authentication:       :plain,
  enable_starttls_auto: false,
  ssl:                  true
}