From: Ronald Fischer Date: 2010-01-18T03:58:44+09:00 Subject: net/smtp authorization exception I can't send email using net/smtp from my mac running OSX 10.4. The SMTP server is run by my Internet Service Provider. Any idea what I'm doing wrong? This is my code: Net::SMTP.start('mail.mnet-online.de',25,'localhost.localdomain', 'ronald.fischer@mnet-online.de','my password goes here', :login) I get the exception /usr/local/lib/ruby/1.8/net/smtp.rb:680:in `check_response': 538 5.7.0 Encryption required for requested authentication mechanism (Net::SMTPUnknownError) Sending mail works fine using the Mac mail.app with the settings which you can see in the attached screenshot. It also works from the shell using mailx. Althought :login seems to be the natural choice for the encryption mechanism, I also tried :plain and the default, but (as expected) with the same effect. I suspect that the 3rd parameter (the HELO domain) is incorrect (I used the default described at http://ruby-doc.org/stdlib/libdoc/net/smtp/rdoc/classes/Net/SMTP.html#M000810), but I don't know what sensible value I should put here. BTW, I tried also the name which is output by uname -n as HELO domain, but with the same result. If you look at the attached screenshot, you can see that mail.app connects to the SMTP server using SSL encryption, so maybe this would be necessary here too, but I have no idea how to mimic this within Ruby. Ronald Attachments: http://www.ruby-forum.com/attachment/4390/screenshot-146.jpg -- Posted via http://www.ruby-forum.com/.