Test this on 37 and master Prerequisites Email should be configured so you can receive emails from moodle based on the docs if you use moodle-docker you can just go to http://localhost:8000/_/mail with $CFG->noemailever = false; Else configure mailcatcher as described here In 'Site Admin' set the following: noreplyaddress to 'noreply@localhost.com' allowedemaildomains to 'localhost.com' Test Log in as admin Go to site admin > Server > Support contact, and remember the following values 'supportname' setting (it may be set to Admin User) 'supportemail' to 'reply@example.com' Go to site admin > development > Make test course and create a XS course, follow the continue button once done. Go to participants, a student should appear there. Make sure ' Insights generated by prediction models ' are all turned ON in the notification preferences for this user. (this is not needed if you use moodle-docker) Replace the student's email address by one you have access to Edit the assignment activity and set its due date to +6 days from today Go to site admin > analytics > analytics settings and untick onlycli setting Go to site admin > analytics > analytics models If the Upcoming activities due model is disabled click on Actions > Enable for Upcoming activities due model Click on Actions > Clear predictions for the Upcoming activities due model Click on Actions > Execute scheduled analysis (or Actions > Get predictions in 3.7) from the Upcoming activities due model Check the student email. You SHOULD see an email, the "From" should include the value in the 'supportname' setting. View the email source and confirm the following headers: From: Admin User <noreply@localhost.com> ReplyTo: Do not reply to this email <noreply@localhost.com> In site admin, add 'example.com' to allowedemaildomains Repeat #6-10 Check the student email. You SHOULD see an email, the "From" should include the value in the 'supportname' setting. View the email source and confirm the following headers: From: Admin User <reply@example.com> or Admin User <reply@example.com> (via xxxx) where xxxx is your site name if $CFG->emailfromvia is enabled ReplyTo: Admin User <reply@example.com>