I managed to get Cucumber, RSpec, Guard, and Spork play nicely with each other in a Rails 3 app, but now I am stuck with the above problem.
Currently I require 'spork/ext/ruby-debug'
in the prefork block of spec_helper.rb
but this works only if I run spork manually, without guard.
This worked for me: Replace your 'guard-spork' gem with this one:
More info on this blog post (in Japanese, but Google translate does a decent job).
The author also created this handy Rails 3 example app to show how to set things up.
Adding Guard to Spork makes it much more useful IMO. I may have to go back to using it now :)