diff --git a/middleman-core/features/directory_index.feature b/middleman-core/features/directory_index.feature
index 9f74daac..b5a79000 100644
--- a/middleman-core/features/directory_index.feature
+++ b/middleman-core/features/directory_index.feature
@@ -8,6 +8,7 @@ Feature: Directory Index
       | needs_index/index.html                        |
       | a_folder/needs_index/index.html               |
       | leave_me_alone.html                           |
+      | wildcard_leave_me_alone.html                  |
       | regular/index.html                            |
       | .htaccess                                     |
     Then the following files should not exist:
@@ -15,6 +16,7 @@ Feature: Directory Index
       | needs_index.html                              |
       | a_folder/needs_index.html                     |
       | leave_me_alone/index.html                     |
+      | wildcard_leave_me_alone/index.html            |
     And the file "needs_index/index.html" should contain "Indexable"
     And the file "a_folder/needs_index/index.html" should contain "Indexable"
     And the file "leave_me_alone.html" should contain "Stay away"
diff --git a/middleman-core/fixtures/indexable-app/config.rb b/middleman-core/fixtures/indexable-app/config.rb
index d770e11f..54b79b5c 100644
--- a/middleman-core/fixtures/indexable-app/config.rb
+++ b/middleman-core/fixtures/indexable-app/config.rb
@@ -1,2 +1,4 @@
 activate :directory_indexes
-page "/leave_me_alone.html", :directory_index => false
\ No newline at end of file
+page "/leave_me_alone.html", :directory_index => false
+
+page "/wildcard*", :directory_index => false
diff --git a/middleman-core/fixtures/indexable-app/source/wildcard_leave_me_alone.html b/middleman-core/fixtures/indexable-app/source/wildcard_leave_me_alone.html
new file mode 100644
index 00000000..5ff5317a
--- /dev/null
+++ b/middleman-core/fixtures/indexable-app/source/wildcard_leave_me_alone.html
@@ -0,0 +1 @@
+Stay away, wildcards!
diff --git a/middleman-core/lib/middleman-core/extensions/directory_indexes.rb b/middleman-core/lib/middleman-core/extensions/directory_indexes.rb
index 4c591c9d..689fb7f6 100644
--- a/middleman-core/lib/middleman-core/extensions/directory_indexes.rb
+++ b/middleman-core/lib/middleman-core/extensions/directory_indexes.rb
@@ -9,63 +9,49 @@ module Middleman::Extensions
       
       # Once registered
       def registered(app)
-        # Include methods
-        app.send :include, InstanceMethods
-        
         app.after_configuration do
           # Register a reroute transform that turns regular paths into indexed paths
           sitemap.reroute do |destination, page|
             new_index_path = "/#{index_file}"
-            frontmatter_ignore = false
 
-            # Check for file and frontmatter
-            d = page.data
-            if !page.data.nil?
-              frontmatter_ignore = d.has_key?("directory_index") && d["directory_index"] == false
-            end
-
-            index_ext = File.extname(index_file)
-
-            # Only reroute if not ignored
+            # Check if it would be pointless to reroute
             path = page.path
-            if ignored_directory_indexes.include? page
-              destination
-            elsif path == index_file || path.end_with?(new_index_path)
-              destination
-            elsif frontmatter_ignore
-              destination
-            elsif index_ext != File.extname(path)
-              destination
-            else
-              destination.chomp(File.extname(index_file)) + new_index_path
+            page_already_index = path == index_file || path.end_with?(new_index_path)
+            if page_already_index || File.extname(index_file) != File.extname(path)
+              next destination
             end
+
+            # Check if frontmatter turns directory_index off
+            d = page.data
+            next destination if d && d["directory_index"] == false
+
+            # Check if file metadata (options set by "page" in config.rb) turns directory_index off
+            # TODO: This is crazy - we need a generic way to get metadata for paths
+            metadata_ignore = false
+            provides_metadata_for_path.each do |callback, matcher|
+              if matcher.is_a? Regexp
+                next if !path.match(matcher)
+              elsif matcher.is_a? String
+                next if !File.fnmatch("/" + matcher.sub(%r{^/}, ''), "/#{path}")
+              end
+              
+              result = instance_exec(path, &callback)
+              if result[:options] && result[:options][:directory_index] == false
+                metadata_ignore = true
+                break
+              end
+            end
+
+            next destination if metadata_ignore
+
+            # Not ignored, so reroute
+            destination.chomp(File.extname(index_file)) + new_index_path
           end
         end
       end
 
       alias :included :registered
     end
-  
-    module InstanceMethods
-      # A list of pages which will not use directory indexes
-      # @return [Array<Middleman::Sitemap::Page>]
-      def ignored_directory_indexes
-        @_ignored_directory_indexes ||= []
-      end
-    
-      # Override the page helper to accept a :directory_index option
-      #
-      # @param [String] url
-      # @param [Hash] options
-      # @return [void]
-      def page(url, options={}, &block)
-        if options.has_key?(:directory_index) && !options["directory_index"]
-          ignored_directory_indexes << sitemap.page(url)
-        else
-          super
-        end
-      end
-    end
   end
   
   # Register the extension