# Using Ruby to send mail through GMail's SMTP servers

16 April, 2012

A few days ago, I ran into a problem.  I have a script set up on my Dreamhost server which occasionally sends me notification emails.  It had been running fine for a couple of weeks, but suddenly they stopped coming through.  I checked the logs and saw I’d been getting an “Access Denied” error from the SMTP server:

Up until this point I’d simply been using ‘localhost’ as my SMTP server, but I guess they might not like me doing that.  I’m not sure whether the servers they use to manage their users’ email are the same as their hosting servers, and either way I’d switched to using Google Apps to manage my email years ago.  The easiest solution, it seemed, was to switch to using Google’s SMTP server.

Connection refused - connect(2) (Errno::ECONNREFUSED)

This is because Google mail only supports TLS/SSL connections (quite sensibly).  Unfortunately, it seems the version of Ruby installed on Dreamhost’s servers by default (1.8.7) doesn’t support TLS connections out of the box.

Thankfully, there’s a gem for that!  If you gem install tlsmail, the enable_tls function becomes available and you can communicate with Google Mail’s servers.

I did all this, but there was still one gotcha.  Using my previous code directly but replacing the servers with Google’s resulted in the following error:

555 5.5.2 Syntax error. yw3sm17774749obb.7 (Net::SMTPFatalError)

Note that this is an SMTP error, rather than a Ruby one.  A little googling turned up this thread, which suggested that the latest ruby version automatically adds angled brackets to the email address you supply to Net::SMTP’s send_message function.  I hadn’t upgraded my Ruby version, but I had made use of the tlsmail gem, so maybe that had done it.

I modified the call so that it specified the email address alone, without the name or angled brackets.  I left the headers in the message itself intact.  It worked!  Here’s the resulting code:

 #!/usr/bin/env ruby require 'rubygems' require 'tlsmail' msg=< To: Test Recipient  Subject: test This is a test EOF Net::SMTP.enable_tls(OpenSSL::SSL::VERIFY_NONE) Net::SMTP.start('smtp.gmail.com', 587, 'domain.com', '[email protected]', 'password', :login) do |smtp|  smtp.send_message msg, "[email protected]", "[email protected]" end

Note this works with mail provided by Google Apps as well as plain vanilla Google Mail. In the latter case, specify “gmail.com” as the domain, otherwise use your own.

Tagged with: gmail, ruby, scripts, smtp