By default IIS will have Rapid-Fail Protection enabled and will restart the pool a maximum of 4 times (5 Errors) if those errors occur within a 5 minute period of each other.
If that is occurring, you’d want to figure out why as well as think about multiple Orchestrator instances for High Availability / Disaster Recovery.
I am not aware of a mechanism out of box to start missed triggers due to a crash. I know if you place Orchestrator into Maintenance Mode it will not restart missed triggers however for each tenant you can review the logs for maintenance and it will indicate which triggers were missed.
How quickly you want to identify the server failure will determine what type of solution you would want but generally speaking you’ll want some script or monitoring tool/application to monitor your resources/logs and act accordingly whether that is to restart the services, or send an alert of sorts.