@Ralph
There may be a Monocle config hack to get it to run other than on 443. The problem then would be that Alexa insists on port 443. I’m pretty sure that if I were still in practice that I could do a transparent proxy pipe to another port on an Apache server on Linux, so you may be able to that with IIS. Monocle likes 127.0.0.1, so that should improve security/performance at least marginally over a true network proxy pipe.