From: Intransition Date: 2010-06-19T07:05:47+09:00 Subject: Re: 1.8.7 SMTP TLS How to? Well, after beating my head again wall for a couple of hours I answer my own question: smtp = Net::SMTP.new(server, port) smtp.enable_starttls smtp.start(domain, account, secret, login) do |s| s.send_message(msg, from, mailto) end Why I was having a problem. This does not work: Net::SMTP.start(server, port, domain, account, secret, login) do |s| s.enable_starttls s.send_message(msg, from, mailto) end ~trans