It's not advisable to run webrick on a production server - in fact,
it's falling out of favour generally as it does have a few bugs.
The latest idea for running on windows is to use mongrel to run the
rails application. You can then use IIS to proxy requests for your
rails site through to the mongrels.
That may be easier said than done as I'm not sure how you proxy on IIS.
However, there has been quite a bit of discussion about the subject of
rails/windows on this group so i would suggest having a bit of a search
to see if you can pick up some additional resources to help you out.
Hope that helps,