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Provides SMTP STARTTLS support for Ruby 1.8.6 (built-in for 1.8.7+). Simply require 'smtp_tls' and use the Net::SMTP#enable_starttls method to talk to servers that use STARTTLS. require 'net/smtp' begin require 'smtp_tls' rescue LoadError end smtp = Net::SMTP.new address, port smtp.enable_starttls smtp.start Socket.gethostname, user, password, authentication do |server| server.send_message message, from, to end