Satish Talim wrote: > Francis, thanks for helping me along. I tried your suggestions. However, > it > still does not work. Do you know the ESMTP command sequence to send an > email > over TSL and Authenticate? Well, maybe try something like this: Use EHLO instead of HELO. After EHLO and before MAIL FROM, send: AUTH PLAIN xxx\r\n where xxx is the base-64 encoding of a string consisting of a binary zero followed by your account name (on the mail server), followed by another binary zero, followed by your password. In Ruby, perhaps something like require 'base64' Base64.encode64( "\000#{username}\000#{psw}" ).chomp -- Posted via http://www.ruby-forum.com/.