Aegis, to be clear, are you saying you’re having issues with 404 handlers specifically? Or something else?
In either case, I’m curious: what would the "recoding" involve, to get around this?
Finally, I’ll note that I have helped more than a few people resolve what seemed ongoing problems with their IIS/CF connection, even though they’d done everything right. There are just way too many moving parts to list in email here all the possible things that could be amiss.
I’ll propose that before you give up, if you wanted to spend even a couple of hours together (per my consulting services, at carehart.org), I may well be able to solve things for you. And if not, and you felt that any or all of the time spent was of no value, you’d not need to pay for that time per my satisfaction guarantee (also discussed on the site).
Hope you may be able to solve things rather than resort to any massive effort.
/charlie