From what I gather on the wiki ( ) running rails in a subdirectory should be pretty much automatic. However I have a rather frustrating set up of fastcgi/rails and IIS. I was forced to modify actionpack/lib/action_controller/request.rb because it was failing to pull the route off the URL correctly (I would always end with the path to the fcgi script instead). def request_uri unless env[''REQUEST_URI''].nil? (%r{^\w+\://[^/]+(/.*|$)$} =~ env[''REQUEST_URI'']) ? $1 : env[''REQUEST_URI''] # Remove domain, which webrick puts into the request_uri. else # REQUEST_URI is blank under IIS - get this from PATH_INFO and SCRIPT_NAME script_filename = env["SCRIPT_NAME"].to_s.match(%r{[^/]+$}) #request_uri = env["PATH_INFO"] request_uri = "" # script_filename contains the path all the way to the script for me... request_uri.sub!(/#{script_filename}/, '''') unless script_filename.nil? request_uri += env["QUERY_STRING"] unless env["QUERY_STRING"].nil? || env["QUERY_STRING"].empty? return request_uri end end This seemed to do what I wanted all the way until I tried to get rails to work within a subdirectory. At this point I''m stuck because although I can hand craft an url to dispatch.fcgi that works, all the link_to links do not have the necessary prefix... I also noticed that relative_url_root is only set for Apache. Is this the only server that rails will "automatically" support a subdirectory on?