Are there any tools to monitor custom console applications on Windows Server? Are there any DevOps tools or known practices to monitor custom made console application on an on premises (Windows Server) environment? 

We developed an exe that needs to be continuously running, and if it fails we would like to know, so we can re-start it. Maybe there are tools to re-start them automatically?
This is probably a question better suited for ServerFault or StackOverflow.

One approach that may work is to Create a Windows Service from an Executable, then set the service to restart on failure/crash.