Background

I recently encountered an interesting problem related to how Virtual Directories interact with web.config when dealing with an HttpHandler. The website was virtually rooted at "/webapp", physically rooted at "C:\inetpub\wwwroot\webapp". Inside the application, I wanted "files" ("/webapp/files") to be physically rooted on another drive at "E:\files" so that large data files could be stored on a more appropriate drive. Furthermore, I wanted a custom Http Handler which would generate a few files inside "files" on the fly. Initially, this was setup by creating a virtual directory named "files" which pointed to "E:\files", the HttpHandler was placed in App_Code, and web.config contained the following:

The Problem

As I quickly found out, this doesn't work (for several reasons, as we will see). First, requests for .txt files are not handled by isapi_aspnet.dll (by default), so whatever is done in the ASP.NET code is irrelevant because IIS will not call ASP.NET to handle the request. To fix this problem, the .txt extension can be added to the list of extensions handled by isapi_aspnet.dll (which will cause extra overhead as each request is run through the ASP.NET ISAPI handler, even when the file exists on disk) or the extension of the generated file can be changed to something mapped to isapi_aspnet.dll (like .aspx).

Next, unless the content of "files" is going to be substantially different from the rest of the application, the "files" Virtual Directory must not be a Virtual Application. If the "files" mapping is really a Virtual Application, it will not share code with the parent application so the HttpHandler class will not be found.

Finally, due to how the ASP.NET Configuration File Hierarchy and Inheritance works, web.config will be (essentially) re-applied in the virtual directory, so "files/generated.aspx" will be "files/files/generated.aspx" when considered from inside of the "files" virtual directory. To fix this (while not also creating a "/generated.aspx" alias as well), remove the httpHandlers section in the global web.config and create a web.config inside of the physical directory for "files" with path="generated.aspx"

Once all of the above steps are completed, the generated file should appear correctly and everything should be golden. If not, I strongly recommend replacing the real content of the custom HttpHandler with code that simply writes a string to the response and exits. This way any internal errors in the HttpHandler will not confound any issues with whether or not the handler is being called.