Hypothetical Automation - "I'm still running!"

Another option is there are many good, affordable uptime monitors (UptimeRobot, Pingdom, BetterUptime, StatusCake) that are and in some cases free (or sub $10/month) if monitoring one site. These can check as frequents as 1 minutes and notify user(s) immediatly. Since a recurring automation will run on the job server the benefit of these are the requests are coming from external vs possibly (internal depending on your IT setup) and the job server may be able to access the site but members cannot. Also, having a service like this that pings means the notification of an alert means something is potentially wrong vs realizing having to realize no notification (i.e. assuming the job send I am still running) means something may be wrong.

I was thinking about those, but our community is entirely internal with no option for external access. You must have very specific credentials (multiple levels) to access the community. So my thought process was something on the platform that effectively needs multiple aspects of the community job service to successfully run.

Is your community able to talk out to a server on the Internet? If so, that does open up some possibilities for automated checking.

Sort of but not easily give our setup, but the solution Michael provided below has worked perfect now for about 2 months. I'm able to quickly see if the community has sent out an e-mail in the past hour which makes keeping an eye on it during nights, weekends, and other times when I'm away much easier.

Sort of but not easily give our setup, but the solution Michael provided below has worked perfect now for about 2 months. I'm able to quickly see if the community has sent out an e-mail in the past hour which makes keeping an eye on it during nights, weekends, and other times when I'm away much easier.

Okay, glad it works for you.

For anyone thinking about alternatives, you could have a similar automation rule, but instead of emailing, you could call/ping a Logic App in Azure. That would be relatively easy to set up to monitor for the lack of a 'ping' and then send you an email alert.