Orchard does not have any mechanism to convert all URLs to lowercase, but due to the fact that Orchard CMS is an ASP.NET MVC application, this can be done with URL rewrite rule + change setting for route and instructing Orchard to lowercase all existing URLs. Redirect to lowercase URLs using IIS URL Rewrite rule.
Take a look at the following. I believe this is your problem. It has to do with the.mvc extension.The problem is that IIS will handle the.mvc file as a static file andwill by default not route the hypothetical.mvc file through your MVCapplication. IIS handles the request and your MVC code never gets achange to route to this file.In summary, here's what the configuration looks like to make.mvc files work:As for it working on IIS7.5, Win 7 without any issues and not IIS 8.5.take a look at this answerThere is also butit doesn't seem to work for MVC4/IIS8 (used to be ok in MVC3/IIS7IIRC). More info.There is also a performance impact with this one as every request willroute through the managed pipeline.Hope all this helps.