The definitive resource for deploying Rails applications on Windows can be found at http://www.pragprog.com/titles/fr_deploy/deploying-rails-applications
The rest of the information in this article is considerably out of date.
It’s pretty safe to say that there is little to no support for deploying Rails applications on Windows. There are lots of people who would love to say goodbye to their .Net infrastructures but need to be able to prove that Ruby on Rails will work in their Microsoft-based environment.
After months of research, including three separate failed attempts to deploy applications on Microsoft’s IIS web server, I have developed several deployment solutions for Windows. Hopefully one of these strategies will work for you.
Visit http://www.napcs.com/howto/rails/deploy/ for more information. Feedback can be sent to me directly.
Also look here: HowToDeployWithLighttpdOnWindows