diff --git a/actionpack/lib/action_controller/routing.rb b/actionpack/lib/action_controller/routing.rb
index 8d51e82..c41fe13 100644
--- a/actionpack/lib/action_controller/routing.rb
+++ b/actionpack/lib/action_controller/routing.rb
@@ -323,7 +323,7 @@ module ActionController
 
           seen_paths = Hash.new {|h, k| h[k] = true; false}
           normalize_paths(paths).each do |load_path|
-            Dir["#{load_path}/**/*_controller.rb"].collect do |path|
+            Dir["#{load_path}/**/*_controller.rb"].sort_by { |path| - path.length }.collect do |path|
               next if seen_paths[path.gsub(%r{^\.[/\\]}, "")]
 
               controller_name = path[(load_path.length + 1)..-1]
diff --git a/actionpack/test/controller/routing_test.rb b/actionpack/test/controller/routing_test.rb
index f480e6d..9534b2c 100644
--- a/actionpack/test/controller/routing_test.rb
+++ b/actionpack/test/controller/routing_test.rb
@@ -629,6 +629,8 @@ class RoutingTest < Test::Unit::TestCase
     ]
 
     assert_equal ["admin/user", "plugin", "user"], ActionController::Routing.possible_controllers.sort
+    assert ActionController::Routing.possible_controllers.index("admin/user") <
+      ActionController::Routing.possible_controllers.index("user")
   ensure
     if true_controller_paths
       ActionController::Routing.controller_paths = true_controller_paths