Ivan,

When using IronRuby.Rack and debugging the ruby code running, keep a few things 
in mind:


1.       Enable debug mode for DLR code in your app’s web.config (in the 
Microsoft.Scripting section).

2.       Because VS breakpoints in blocks don’t work yet, using Debug.Assert 
will do the job.

3.       IIS has a timeout of 60 seconds per request, which can be annoying 
when debugging. In the AppPool configuration that your application is running 
in try to max the timeout out so the process you want to debug stays around.

4.       Use WinDBG if you want to “man up”, but the VS debugger will be just 
fine.

Ivan, your “No route matches "/mocktwitter" with {:method=>:get}” error is 
because you need to tell Rails what the root directory on the web-server is so 
it can route appropriately. To see how to do this, look at the 
IronRuby.Rails.Example 
environment.rb<http://github.com/ironruby/ironruby/blob/master/Merlin/Main/Hosts/IronRuby.Rack/IronRuby.Rails.Example/config/environment.rb#L10>:

Rails::Initializer.run do |config|
  config.action_controller.relative_url_root = "/IronRuby.Rails.Example" if 
ENV['RACK_ENV'] == 'production'
  # …
end

Also, I usually set up a separate AppPool, and set it to run as a specific 
Windows user, so I can grant read-only permissions to that user for the Ruby 
stdlib/gems, and read-write access for the app. Then you don’t have to grant 
permissions to IIS_IUSRS for all your stuff.

~js
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