PLEASE NOTE: Native Lighttpd Windows builds are available at en.wlmp-project.net/
The last available Lighttpd for Windows build that I created using Cygwin was Lighttpd for Windows 1.4.17. Updated September 29, 2009.

The following mini-tutorial will get you started on setting up a Ruby on Rails development environment. Please note that I do not know how to program in Ruby. 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 gets you up and running with lighttpd rather than Ruby’s built-in WEBrick web server.
This is NOT intended for production machines. If you fail to follow that advice, you are on your own. In fact, I’m not responsible for anything that you do to your machine. I have tested the following instructions on my machine, and it worked fine; I believe it will work for yours as well. Now that I have claimed no responsibilities for any screw-ups that you may inflict on your computer, here’s the tutorial:

Download RubyForge’s One-Click Ruby Installer: http://rubyforge.org/frs/?group_id=167
Choose the latest “Stable Release” which as of this writing is 1.8.2-15 (ruby182-15.exe).
1. Run the downloaded executable and follow the instructions. Accepting the defaults should be fine unless you have specific reasons to do otherwise.
2. Now install Rails by opening a command window (Start–>Run–>type in ‘cmd’ and press Enter) and then running the command ‘gem install rails –remote’ (without surrounding quotes) and answer “y” for yes to all the dependency questions. UPDATE: please note that the above command has 2 dashes before ‘remote’. WordPress makes two consecutive dashes appear as one.
Download MySQL 4.1 (Windows Essentials 4.1.16 in this case) from a mirror closest to your location: http://dev.mysql.com/get/Downloads/MySQL-4.1/mysql-essential-4.1.16-win32.msi/from/pick#mirrors
1. Run the downloaded MSI installer and accept the defaults, and skip the MySQL.com account sign-up.
2. After clicking ‘Finish’, a configuration wizard will come up. Accept all the defaults except in the security panel you MUST uncheck “Modify Security Settings”. If you fail to do this, Rails will have problems.

Install lighttpd for Windows (download from (link to lighttpd tag on my site)) :
1. Install the downloaded executable. Simply follow the directions within the setup.
2. Edit C:lighttpdetclighttpd.conf; set the server.document-root = “C:/rails/cookbook/public”
3. Optionally: change the port number to 81: just uncomment the line that says “server.port = 81”. If you do this step, make sure that in the next section you point to http://127.0.0.1:81

Create an empty Rails application:
1. In the cmd window, type in:
md rails
then:
cd rails
then:
rails cookbook
2. Start lighttpd (Start–>Programs–>lighttpd–>Start lighttpd or double-click the desktop icon if you installed it).
3. Go to http://127.0.0.1 in your web browser. You should see a page that says “Welcome aboard”.

From this point on, I am assuming that you know how to proceed. After all I do not know how to program in Ruby. I hope you found this useful…