After some further testing, this seems a little bazaar.

The following code will run both the Subdomain and Authenticated constraints 
when accessing a resource:

scope :constraints => Subdomain.new do
  resources :something, :constraints => Authenticated.new
end

However, with the root route specified (your scenario), it only runs the 
constraint attached directly to the root route. Not sure if this is a bug, 
or the intended behavior of the root route.

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