Here\'s my simple test program (using ActionMailer 3.0.8, Ruby 1.9.2p180 Mac OS X):
require \'rubygems\'
require \'action_mailer\'
ActionMailer::Base.delive
had similar network issues. use the code below in irb
to get debug info right in the console.
require 'net/smtp'
smtp = Net::SMTP.new('ip_or_dns_address', port)
smtp.debug_output = $stdout
smtp.enable_starttls_auto#skip if not needed
smtp.start("domain", "user", "password", auth_type)
never really found out what the issue was. they moved the exchange server and the production server stopped sending emails. im not really an IT guy but there were different debug logs depending which part of the network i was on. finally "solved" the problem by sending unauthenticated email...