Ruby on Rails on IIS?
you must like pain because this deployment is going to hurt. I don't know if this is a solution for you, but at my old job we were deploying web apps on windows tablets (over 200 of them) and decided to use virtual box and deploy the app in the vm. One of our old apps on the pc tablets we deployed on windows without iis, just using ruby and rubygems with mongrel as the app server and mysql as the database but it was not pleasurable.
Microsoft's Web Platform Installer makes it all surprisingly easy! See http://www.helicontech.com/articles/ruby-on-rails-on-windows-in-production/ for details.