Pre-requisites Setup mailcatcher to keep tabs on the SMTP connections. Andrew Nicols has a branch with more logging (necessary in order to complete this test): sudo apt-get install ruby1.9.1-dev cd to your friendly git folder git clone git@github.com:andrewnicols/mailcatcher.git cd mailcatcher git checkout connectionLogging sudo gem build mailcatcher.gemspec sudo gem install mailcatcher-0.6.0.gem mailcatcher -vf # (you will watch this window) Install failmail cd mod/ # in your moodle instance git clone git@github.com:xow/moodle-mod_failmail.git failmail Go to Home ► Site administration ► Notifications Follow the prompts to install failmail Test Go to Home ► Site administration ► Plugins ► Message outputs ► Email Set SMTP hosts to "127.0.0.1:1025" Set SMTP session limit to 10 Make sure that your browser doesn't auto fill the SMTP username and password . If it does, just delete both. When did they become so over-zealous anyway? php admin/tool/task/cli/schedule_task.php --execute='\mod_failmail\task\cron_task' This will send 30 emails. Watch your mailcatcher screen, and check that a new connection is established every 10 emails. ==> SMTP: Connected established ==> SMTP: Received message from '<john@moodle.com>' (746 bytes) ==> SMTP: Received message from '<john@moodle.com>' (746 bytes) ==> SMTP: Received message from '<john@moodle.com>' (746 bytes) ==> SMTP: Received message from '<john@moodle.com>' (746 bytes) ==> SMTP: Received message from '<john@moodle.com>' (746 bytes) ==> SMTP: Received message from '<john@moodle.com>' (746 bytes) ==> SMTP: Received message from '<john@moodle.com>' (746 bytes) ==> SMTP: Received message from '<john@moodle.com>' (746 bytes) ==> SMTP: Received message from '<john@moodle.com>' (746 bytes) ==> SMTP: Received message from '<john@moodle.com>' (746 bytes) ==> SMTP: Connected closed