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copied!<p>I actually just got this working. Wrote a quick script to test it.</p> <p>I was getting a different error than you were (requiring STARTTLS), I also found I had to use port 587 instead of 465.</p> <p>I found the trick to get it working in a Rails plugin I found. (agilewebdevelopment.com/plugins/net_smtp_tls_support)</p> <p>if you 'eval' this file (it adds tls support to the standard Net::SMTP library): </p> <blockquote> <p><a href="http://happiness-is-slavery.net/wp-content/rails-plugins/smtp_add_tls_support/lib/smtp_add_tls_support.rb" rel="noreferrer">http://happiness-is-slavery.net/wp-content/rails-plugins/smtp_add_tls_support/lib/smtp_add_tls_support.rb</a></p> </blockquote> <p>then run 'Net::SMTP.enable_tls()'</p> <p>everything seems to work fine.</p> <p>Here's my code:</p> <pre><code>require 'rubygems' require 'net/smtp' eval File.read("smtp_tls.rb") Net::SMTP.enable_tls() FROM_EMAIL = "REMOVED" PASSWORD = "REMOVED" TO_EMAIL = "REMOVED" msgstr = <<END_OF_MESSAGE From: Your Name <#{FROM_EMAIL}> To: my phone <#{TO_EMAIL}> Subject: text message Date: Sat, 23 Jun 2001 16:26:43 +0900 Message-Id: <unique.message.id.string@example.com> This is a test message. END_OF_MESSAGE Net::SMTP.start('smtp.gmail.com', 587, 'gmail.com', FROM_EMAIL, PASSWORD, :plain) do |smtp| smtp.send_message msgstr, FROM_EMAIL, TO_EMAIL end </code></pre> <p>obviously, i downloaded the above mentioned file to the same directory and named it 'smtp_tls.rb'</p> <p>Hope this helps!</p>

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