Troubleshooting 500 Internal Server Errors on IIS 8.5?

How does one tell the difference between an HTTP / HTTPS request that is failing in an ASP .NET Core application, and one that’s failing from an IIS mis-configuration?

Most of the time IIS and the ASP .NET Core have different logs, and the solution is often just to turn off HTTPS to figure out which is returning the error, but the error messages from IIS just seem to be along the lines of HTTP 500 Internal Server Error in the output of a W3C formatted log message, and they don’t specify anything deeper than that.

As far as I can tell, ASP .NET Core applications just sit behind IIS and requests/responses are kind of reverse proxied to the actual application.

I came across the following IIS configuration setting in which you can enable the tracing of failed requests, and it seems to specify that it will gladly log the deeper error messages as HTTP 500 Internal Server Error is mentioned at the bottom of that documentation, but I’m uncertain of this.