1/ setup up a few courses with manually enrolled users with different expiration dates 2/ set up expiration notification hour in enrol_manual settings and in course instances enable notification and set up thresholds 3/ execute cron or enrol/manual/cli/sync.php script 4/ verify mails and messages Note: you may want to modify value of last execution flag instead of waiting the whole day, such as by executing: set_config('notifylast', time()-(60*60*24), 'enrol_manual');