Send email from Ruby program with TLS

Question

I am trying to send an email from a Ruby program. The smtp server is an Exchange 2007 server that requires me to login to send the email.

#!/usr/bin/ruby

require 'rubygems'
require 'net/smtp'

msgstr = "Test email."

smtp = Net::SMTP.start('smtp.server.com', 587, 
  'mail.server.com', 'username', 'password', :login) do |smtp|
    smtp.send_message msgstr, 'from@server.com', 'to@server.com'
end

When I run this I get the following error.

/usr/lib/ruby/1.8/net/smtp.rb:948:in `check_auth_continue': 
530 5.7.0 Must issue a STARTTLS command first (Net::SMTPAuthenticationError)
    from /usr/lib/ruby/1.8/net/smtp.rb:740:in `auth_login'
    from /usr/lib/ruby/1.8/net/smtp.rb:921:in `critical'
    from /usr/lib/ruby/1.8/net/smtp.rb:739:in `auth_login'
    from /usr/lib/ruby/1.8/net/smtp.rb:725:in `send'
    from /usr/lib/ruby/1.8/net/smtp.rb:725:in `authenticate'
    from /usr/lib/ruby/1.8/net/smtp.rb:566:in `do_start'
    from /usr/lib/ruby/1.8/net/smtp.rb:525:in `start'
    from /usr/lib/ruby/1.8/net/smtp.rb:463:in `start'

I can't find anything in the Ruby api for Net::SMTP referencing TLS or a STARTTLS command.

EDIT: Download smtp-tls.rb, the code doesn't change much but here is what I got to work.

#!/usr/bin/ruby

require 'rubygems'
require 'net/smtp'
require 'smtp-tls'

msgstr = <<MESSAGE_END
From: me <me@test.com>
To: you <you@test.com>
Subject: e-mail test

body of email

MESSAGE_END

smtp = Net::SMTP.start('smtp.test.com', 587, 'test.com', 'username', 'passwd', :login) do |smtp|
    smtp.send_message msgstr, 'me@test.com',  ['you@test.com']
end

EDIT: Works with ruby 1.8.6

The accepted answer is not correct (or at least, not anymore). — Nathan Long, Mar 29 '14 at 19:51

score 14 · Answer 1 · edited May 23 '17 at 12:25

14

No gem required in Ruby 1.9.3

You don't need a gem to do this (at least, not for Gmail and Ruby 1.9.3), the documentation is just terrible.

See https://stackoverflow.com/a/3559598/4376

edited May 23 '17 at 12:25

Community

1
1

answered Nov 24 '12 at 17:11

Nathan Long

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score 5 · Answer 2 · answered Nov 04 '09 at 19:16

5

I couldn't get it working using your updated example. But the following did work for me.

require 'rubygems'
require 'smtp_tls'
require 'net/smtp'

smtp = Net::SMTP.new 'smtp.gmail.com', 587
smtp.enable_starttls

smtp.start(Socket.gethostname,username,password,:login) do |server|
   server.send_message msg, from, to
end

answered Nov 04 '09 at 19:16

brodie31k

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What version of Ruby are you using? – Mark Nov 06 '09 at 13:44
I'm in 1.8.7 and get an "unknown method 'enable_starttls' error". I've required smtp_tls and net/smtp. One possible problem is that in my config i have `ActionMailer::Base.delivery_method = :smtp`. Should this perhaps be set to something else eg smtp_tls or something? – Max Williams Jun 06 '11 at 11:32
I tried to install smtp_tls but I it said: `smtp_tls requires Ruby version ~> 1.8.6.0.` – Daniel Hernández May 13 '12 at 00:30
and `smtp.enable_tls` for straight TLS instead of `smtp.enable_starttls` – Claire Furney Jul 02 '22 at 19:46

score 1 · Accepted Answer · answered Jun 26 '09 at 21:45

1

Net::SMTP doesn't look like it supports startTLS encryption. I did find a project on github that has code for dealing with this, though.

smtp-tls

answered Jun 26 '09 at 21:45

BaroqueBobcat

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score 0 · Answer 4 · answered May 13 '12 at 00:50

0

This is a solution using the tlsmail gem:

require 'rubygems'
require 'tlsmail'
require 'net/smtp'

Net::SMTP.enable_tls(OpenSSL::SSL::VERIFY_NONE)
Net::SMTP.start(server,25,Socket.gethostname,username,password,:login) do |server|
  server.send_message msg, from, to
end

answered May 13 '12 at 00:50

Daniel Hernández

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This was the winning formula for me with Ruby 1.9.3, but I made one change: I specified port 587 rather than port 25. – fearless_fool Oct 14 '12 at 06:58

Send email from Ruby program with TLS

4 Answers4

No gem required in Ruby 1.9.3