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POSend email from Ruby program with TLS
 

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    <p>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.</p> <pre><code>#!/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 </code></pre> <p>When I run this I get the following error.</p> <pre><code>/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' </code></pre> <p>I can't find anything in the <a href="http://www.ruby-doc.org/core/classes/Net/SMTP.html" rel="noreferrer">Ruby api for Net::SMTP</a> referencing TLS or a STARTTLS command.</p> <p><strong>EDIT: Download smtp-tls.rb, the code doesn't change much but here is what I got to work.</strong></p> <pre><code>#!/usr/bin/ruby require 'rubygems' require 'net/smtp' require 'smtp-tls' msgstr = &lt;&lt;MESSAGE_END From: me &lt;me@test.com&gt; To: you &lt;you@test.com&gt; 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 </code></pre> <p><strong>EDIT: Works with ruby 1.8.6</strong></p>
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