I have an IIS web application where there are hundreds of URL rewrite definitions in the Web.config file. It seems that each of the rules is being evaluated for each request, so it seems to me like at least a little of overhead.
I have been trying to figure it out in Dynatrace, but I'm a little limited because I'm experiencing this in an Azure web-app application. I don't see anything interesting in IIS Modules Insight, and have also tried the Method Hotspot approach, but with no relevant data.
Has anyone ever had an encounter with such a large number of rules, and measured it's impact in Dynatrace?
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You can't measure it in Dynatrace itself. Method hotspots are operating on .NET level, not IIS itself. In general best way to determine what possible overhead could be is by checking what is avg time between starting processing request on IIS side and .NET side of the application. This time delta is what you are looking for. If this application has issues with this time and you don't see anything in modules, this may be a root cause of overhead. If you see that requests came from IIS to .NET without any time loss, it's not affecting the application (which doesn't know that such a situation should exist for many reasons).