I have the same problem, that is :
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on IIS7, on a WebApplication in .Net 2
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with a wildcard to ASP.Net (for instance to manage RewritePath on Image)
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I have "Failed to Execute URL" on any static file (jpg, css, js...)
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WebApplication in "Classic ASP.Net" mode
I have follow the instuction to make the wildcard to ASP.Net, by adding this code on web.config:
<configuration>
<system.webServer>
<handlers>
<clear />
<add name="Wildcard" path="*" verb="*" modules="IsapiModule" resourceType="Unspecified"
scriptProcessor="%windir%\Microsoft.NET\Framework\v2.0.50727\aspnet_isapi.dll" />
</handlers>
</system.webServer>
</configuration>
After that, the wildward works but my "page" does not render any of image and no ressources is loaded (css, js...).
When i put directly the URL of an image for instance, I have the "Failed to Execute URL". The problem is inside the DefaultHttpHandler that is the default handler for files that is not directly managed by ASP.Net
I have just understood that DefaultHttpHandler try to redirect the request to IIS and it is not allowed in IIS7. This behavior allow to server page that need other ISAPI filters (like .asp, .php, .exe, .dll, and so on).
If you don't need this behavior but just need to serve static files (jpg, css, js...), you can add this lines to web.config:
<configuration>
<system.web>
<httpHandlers>
<remove path="*" verb="GET,HEAD,POST" />
<add path="*" verb="GET,HEAD,POST" type="System.Web.StaticFileHandler" validate="True" />
</httpHandlers>
</system.web>
</configuration>
This consist to remove the DefaultHttpHandler for all non managed ressources to the StaticFileHandler.
It works for me.
Bye
Ludovic.