@Vincent-TP Yup. It's configured correctly. The Test Email button works perfectly and sends me an email. I did have to enable Event Emails, but it made no difference.

What decade was that help link from? My interface was totally different. My "Mail Server" was actually in Global->Settings->Server Settings.

The other settings were at: Site->Logs->Notifications->Alert->Alert Emails and Site->Logs->Notifications->Event->Event Emails

I made sure all those options in the help link were enabled and setup correctly, and the test button sent an email.

BTW, Global->Settings->Server Settings->Sender Address doesn't work. I put something in there, but the email still says it's from me, the email address in Username to log into the SMTP server (From: Omada SDN Controller <my_email_address>). I'm guessing it's probably because of all those security measures in place with email to not allow email to be impersonated and the From field to be changed.

EDIT: I got it to work! I had to change Global->Settings->Server Settings->Sender Address to the same as Username email address. I think maybe my SMTP server is rejecting the email because the From field is something other than my username email address. But it's weird that the Test Email button works, probably just a bug.

Also, the (?) help link in the controller states "Sender Address: Specify the sender address of the email. If you leave it blank, the controller will uses your email address as the sender address.". But, I cannot leave Sender Address blank, it won't let me click Apply. A slight bug in the interface.