We recently encountered a problem where there was an issue with the Alert Engine had lost connection to the database due to the maximum number of connections to the database being reached. This caused all alerting for Orion to stop and meant that when we had things go down emails did not get generated to notify us that it was down. I'm currently trying to use task scheduler to work as a backup but there isn't really a good way for it to tell you whats wrong it will just flag it as an error and you have to go look at it to see if it's something fatal or not.
I would like to see some sort of feature added as a method of letting you know if there is an internal failure has occurred and alerts are not being sent out. Like a heart beat monitoring process that attempts to generate an alert and only sends an email if the alert could not be generated.