Load IIS Manager
Bring up the "Properties" page for the appropriate web site (I expand
the machine, then "Web Sites" then right-click -> Properties on the Web
Site my application is hosted on)
Select the "Home Directory" tab
Click the "Configuration..." button near the bottom-right corner
Double-click the application extension (in this case .ASHX)
In the botton-left corner there should be a checkbox labeled "Verify
that file exists"

In my configuration it was checked, which I think is actually the
default when adding an extension mapping by hand...which I had to do
earlier this week to get ASP.NET to run at all.  Apparently, if it's
checked, it will serve up a 404 if the file doesn't exist, before even
going to an httpHandler that you might have defined, so the whole
"on-the-fly file generation" thing gets broken.

-- Joe


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