Did you try to debug your routes using the Phil Haack route debugger on the server?
Edit:
In IIS 7.5, you donโt need any special handler without extension, it is processed automatically, you do not need to change anything. As far as I know, this is only necessary for IIS 6. Could this be a problem? what if you remove this special handler? perhaps this is what stops him to start moving along the route.
Edit:
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EDIT:
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