Your comments

Got a call with support next week.  Will update with results, and mention the above to them.

Reply from support regarding this issue:
"...we do still have a bug report (it's a new one) registered for the trigger emails not sending out in 20.11.xxxx+; the bug report that you linked to is also linked internally to our bug report with development, so once the development ticket is resolved, that public report will also close. You may also follow along with our Output Stream here for updates when the new versions are released (it will mention the trigger emails specifically).

As of 20.11.914, trigger bug still seems to be present, but not showing up in the others, so hard to track on here (or am I reading it wrong, and they fixed it in subsequent builds, and that's why it's not listed?).

We have a lot of the first type of trigger, which tells us when a machine goes offline (and its counterpart that tells us when the machine is back online).  Helps monitor connectivity without resorting to more 3rd party software to monitor it.

Connectwise support got back to me as well, saying that they are aware that this is still an active bug, and are working on it.  See below.

This is not the case for us.  We do not have such a trigger.  

We're on almost the same version.  20.11.1385.7587

I wouldn't hold my breath.  Ours would also work for several hours, but then stop.

I've got an active case with support right now.  Got escalated to L2 earlier today.  Will update with solution when there is one.

Note at top says "waiting for information".  Maybe Steven is not available.  Can I provide information?  What are you looking for?

We're also still having problems with the triggers.  

We have been having issues for a while, followed the thread here:
But then in the last post it was announced that version 20.9 has fixed it, and thread was closed.  Issues did not go away completely (maybe takes a few hours before triggers stop working, whereas before it was minutes).

Email test works, then it works for a while, and stops.

Self-hosted, latest official release, all extensions updated, plain email triggers for host up/down or for someone sending a chat message, e.g.

Event.EventType = 'Disconnected' AND Session.SessionType = 'Access' AND Connection.ProcessType = 'Guest' AND Session.Name = 'mainserver' AND Session.CustomProperty1 = 'client1'


Event.EventType = 'SentMessage' AND Connection.ProcessType = 'Guest' AND Session.HostConnectedCount = 0

Upgraded from 20.8 to 20.9 a few days ago, also noticed that there's an update to the advanced SMTP extension, which I installed.  Triggers worked for a couple of days, then stopped again  :(