Your monitoring catches problems on everything except itself. Here is how an always-firing Watchdog alert plus an external heartbeat check turns silence into a signal, so you find out when your own alerting dies.
TL;DR
A monitoring system can't reliably monitor its own failure, so use a dead man's switch. Create an always-firing Prometheus Watchdog alert and route it to an independent external heartbeat service. As long as the monitoring pipeline is working, the Watchdog continuously refreshes the heartbeat. If Prometheus, Alertmanager, or the delivery path fails, the heartbeat stops and the external service alerts you through a separate channel. The key is independence: the system responsible for detecting that your monitoring is down must not depend on the monitoring stack itself.
One of the traps of creating alerts on a monitoring stack is the hidden assumption that the mechanism evaluating the alert is running properly and has the ability to evaluate it. Prometheus watches your hosts and Alertmanager delivers the warnings. But what watches Prometheus? If something goes wrong and the monitoring stack fails in the middle of the night, no alerts are going out but there is definitely a problem. That is the failure mode that you should be most concerned about, because it is the one your monitoring cannot report on.
