Here are a couple of tutorials on installing Ruby on Rails on a Windows box. First is Kevin Worthington's "Ruby on Rails (RoR) with lighttpd on Windows (getting started)":

The following mini tutorial will start you on your way to setting up a Ruby on Rails development environment. Please note that I do not know how to program in the Ruby language. I am providing this tutorial due to the number of requests that I have received in the posts related to lighttpd. Please note that this basically gets you up and running and using lighttpd rather than Ruby's built-in WEBrick web server.

And from the Rails wiki, is How To Deploy With Lighttpd On Windows. Where the first tutorial is more on getting everything installed, this one from the wiki goes into a little more detail on configuring Lighttpd on a Windows box.

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