diff --git a/middleman-core/features/wildcard_page_helper.feature b/middleman-core/features/wildcard_page_helper.feature
index baa75556..5ac7a25e 100644
--- a/middleman-core/features/wildcard_page_helper.feature
+++ b/middleman-core/features/wildcard_page_helper.feature
@@ -15,5 +15,5 @@ Feature: Wildcards in Page helper
     Then I should see "Normal Layout"
     When I go to "/admin/"
     Then I should see "Admin Layout"
-    When I go to "/admin/page.html"
+    When I go to "/admin/page/"
     Then I should see "Admin Layout"
\ No newline at end of file
diff --git a/middleman-core/lib/middleman-core/base.rb b/middleman-core/lib/middleman-core/base.rb
index 8c9d02a4..7ab77383 100644
--- a/middleman-core/lib/middleman-core/base.rb
+++ b/middleman-core/lib/middleman-core/base.rb
@@ -370,13 +370,13 @@ class Middleman::Base
     
     # Run before callbacks
     run_hook :before
-    
-    # Return 404 if not in sitemap
-    return not_found unless sitemap.exists?(@request_path)
-    
+
     # Get the page object for this path
-    sitemap_page = sitemap.page(@request_path)
-    
+    sitemap_page = sitemap.page_by_destination(@request_path)
+
+    # Return 404 if not in sitemap
+    return not_found unless sitemap_page
+
     # Return 404 if this path is specifically ignored
     return not_found if sitemap_page.ignored?
 
@@ -494,4 +494,4 @@ protected
     end
     res['Content-Type'] = mime_type
   end
-end
\ No newline at end of file
+end
diff --git a/middleman-core/lib/middleman-core/cli/build.rb b/middleman-core/lib/middleman-core/cli/build.rb
index fc6913e4..c2e0f567 100644
--- a/middleman-core/lib/middleman-core/cli/build.rb
+++ b/middleman-core/lib/middleman-core/cli/build.rb
@@ -99,27 +99,20 @@ module Middleman::Cli
     # Ignore following method
     desc "", "", :hide => true
     
-    # Render a template to a file.
+    # Render a page to a file.
     #
-    # @param [String] source
-    # @param [String] destination
-    # @param [Hash] config
-    # @return [String] the actual destination file path that was created
-    def tilt_template(source, destination, config={})
+    # @param [Middleman::Sitemap::Page] page
+    # @return [void]
+    def tilt_template(page)
       build_dir = self.class.shared_instance.build_dir
-      request_path = destination.sub(/^#{build_dir}/, "")
-      config[:force] = true
+      output_file = File.join(self.class.shared_instance.build_dir, page.destination_path)
 
       begin
-        destination, request_path = self.class.shared_instance.reroute_builder(destination, request_path)
-
-        response = self.class.shared_rack.get(request_path.gsub(/\s/, "%20"))
-
-        create_file(destination, response.body, config)
-
-        destination
+        response = self.class.shared_rack.get(page.request_path.gsub(/\s/, "%20"))
+        create_file(output_file, response.body, { :force => true })
       rescue
-        say_status :error, destination, :red
+        say_status :error, output_file, :red
+        puts $!
         abort
       end
     end
@@ -213,6 +206,8 @@ module Middleman::Cli
       # Sort paths to be built by the above order. This is primarily so Compass can
       # find files in the build folder when it needs to generate sprites for the
       # css files
+
+      # TODO: deal with pages, not paths
       paths = @app.sitemap.all_paths.sort do |a, b|
         a_ext = File.extname(a)
         b_ext = File.extname(b)
@@ -225,21 +220,15 @@ module Middleman::Cli
 
       # Loop over all the paths and build them.
       paths.each do |path|
-        file_source = path
-        file_destination = File.join(given_destination, file_source.gsub(source, '.'))
-        file_destination.gsub!('/./', '/')
+        page = @app.sitemap.page(path)
 
-        if @app.sitemap.proxied?(file_source)
-          file_source = @app.sitemap.page(file_source).proxied_to
-        elsif @app.sitemap.page(file_source).ignored?
-          next
-        end
-        
-        next if @config[:glob] && !File.fnmatch(@config[:glob], file_source)
+        next if page.ignored?
+        next if @config[:glob] && !File.fnmatch(@config[:glob], path)
 
-        file_destination = base.tilt_template(file_source, file_destination)
+        base.tilt_template(page)
 
-        @cleaning_queue.delete(Pathname.new(file_destination).realpath) if cleaning?
+        output_path = File.join(@destination, page.destination_path)
+        @cleaning_queue.delete(Pathname.new(output_path).realpath) if cleaning?
       end
     end
   end
diff --git a/middleman-core/lib/middleman-core/core_extensions/builder.rb b/middleman-core/lib/middleman-core/core_extensions/builder.rb
index 5ba2b160..7f67222b 100644
--- a/middleman-core/lib/middleman-core/core_extensions/builder.rb
+++ b/middleman-core/lib/middleman-core/core_extensions/builder.rb
@@ -16,7 +16,8 @@ module Middleman::CoreExtensions::Builder
   # Build Class Methods
   module ClassMethods
     # Get a list of callbacks which can modify a files build path
-    #
+    # Each callback takes a destination path and a request path and
+    # returns a new destination path, or false if it doesn't want to reroute.
     # @return [Array<Proc>]
     def build_reroute(&block)
       @build_rerouters ||= []
@@ -29,14 +30,14 @@ module Middleman::CoreExtensions::Builder
   module InstanceMethods
     # Run through callbacks and get the new values
     #
-    # @param [String] destination The current destination of the built file
-    # @param [String] request_path The current request path of the file
-    # @return [Array<String>] The new values
+    # @param [String] destination The current destination path of the built file
+    # @param [String] request_path The request path of the file
+    # @return [String] The new destination path
     def reroute_builder(destination, request_path)
       result = [destination, request_path]
       
       build_reroute.each do |block|
-        output = instance_exec(destination, request_path, &block)
+        output = block.call(destination, request_path)
         if output
           result = output
           break
diff --git a/middleman-core/lib/middleman-core/core_extensions/routing.rb b/middleman-core/lib/middleman-core/core_extensions/routing.rb
index d5ec1808..6be37409 100644
--- a/middleman-core/lib/middleman-core/core_extensions/routing.rb
+++ b/middleman-core/lib/middleman-core/core_extensions/routing.rb
@@ -64,7 +64,7 @@ module Middleman::CoreExtensions::Routing
 
       # Setup proxy
       if opts.has_key?(:proxy)
-        reroute(url, opts[:proxy])
+        proxy(url, opts[:proxy])
         
         if opts.has_key?(:ignore) && opts[:ignore]
           ignore(opts[:proxy])
@@ -89,4 +89,4 @@ module Middleman::CoreExtensions::Routing
       end
     end
   end
-end
\ No newline at end of file
+end
diff --git a/middleman-core/lib/middleman-core/core_extensions/sitemap.rb b/middleman-core/lib/middleman-core/core_extensions/sitemap.rb
index a2c7e6b9..4366d976 100644
--- a/middleman-core/lib/middleman-core/core_extensions/sitemap.rb
+++ b/middleman-core/lib/middleman-core/core_extensions/sitemap.rb
@@ -74,10 +74,10 @@ module Middleman::CoreExtensions::Sitemap
     # @param [String] url
     # @param [String] target
     # @return [void]
-    def reroute(*args)
+    def proxy(*args)
       sitemap.proxy(*args)
     end
-    
+
     # Register a handler to provide metadata on a file path
     # @param [Regexp] matcher
     # @return [Array<Array<Proc, Regexp>>]
@@ -96,4 +96,4 @@ module Middleman::CoreExtensions::Sitemap
       @_provides_metadata_for_path
     end
   end
-end
\ No newline at end of file
+end
diff --git a/middleman-core/lib/middleman-core/extensions/directory_indexes.rb b/middleman-core/lib/middleman-core/extensions/directory_indexes.rb
index 1c8ea2df..4c591c9d 100644
--- a/middleman-core/lib/middleman-core/extensions/directory_indexes.rb
+++ b/middleman-core/lib/middleman-core/extensions/directory_indexes.rb
@@ -12,83 +12,43 @@ module Middleman::Extensions
         # Include methods
         app.send :include, InstanceMethods
         
-        # Before requests
-        app.before do
-          prefix           = @original_path.sub(/\/$/, "")
-          indexed_path     = prefix + "/" + index_file
-          extensioned_path = prefix + File.extname(index_file)
-          
-          is_ignored       = false
-          fm_ignored       = false
-          
-          # If the sitemap knows about the path
-          if sitemap.exists?(@original_path)
-            # Inspect frontmatter
-            d = sitemap.page(@original_path).data
-            
-            # Allow the frontmatter to ignore a directory index
-            if !d.nil? && d.has_key?("directory_index") && d["directory_index"] == false
-              fm_ignored = true
-            else
-              next
-            end
-          else
-            # Otherwise check this extension for list of ignored indexes
-            is_ignored = ignored_directory_indexes.include?(extensioned_path)
-          end
+        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
 
-          # If we're going to remap to a directory index
-          if !sitemap.exists?(indexed_path) && !is_ignored && !fm_ignored
-            parts         = @original_path.split("/")
-            last_part     = parts.last
-            last_part_ext = File.extname(last_part)
-        
-            # Change the request
-            if last_part_ext.blank?
-              # This is a folder, redirect to index
-              @request_path = extensioned_path
-            end
-          end
-        end
-      
-        # Basically does the same as above, but in build mode
-        app.build_reroute do |destination, request_path|
-          index_ext      = File.extname(index_file)
-          new_index_path = "/#{index_file}"
-          frontmatter_ignore = false
-
-          # Check for file and frontmatter
-          if sitemap.exists?(request_path)
-            p = sitemap.page(request_path)
-            d = p.data
-            if !d.nil?
+            # Check for file and frontmatter
+            d = page.data
+            if !page.data.nil?
               frontmatter_ignore = d.has_key?("directory_index") && d["directory_index"] == false
             end
-          end
 
-          # Only reroute if not ignored
-          if ignored_directory_indexes.include?(request_path)
-            false
-          elsif request_path =~ /#{new_index_path}$/
-            false
-          elsif frontmatter_ignore
-            false
-          else
-            [
-              destination.sub(/#{index_ext.gsub(".", "\\.")}$/, new_index_path),
-              request_path
-            ]
+            index_ext = File.extname(index_file)
+
+            # Only reroute if not ignored
+            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
+            end
           end
         end
       end
-      
+
       alias :included :registered
     end
   
-    # Directory indexes instance methods
     module InstanceMethods
       # A list of pages which will not use directory indexes
-      # @return [Array<String>]
+      # @return [Array<Middleman::Sitemap::Page>]
       def ignored_directory_indexes
         @_ignored_directory_indexes ||= []
       end
@@ -100,7 +60,7 @@ module Middleman::Extensions
       # @return [void]
       def page(url, options={}, &block)
         if options.has_key?(:directory_index) && !options["directory_index"]
-          ignored_directory_indexes << url
+          ignored_directory_indexes << sitemap.page(url)
         else
           super
         end
@@ -110,4 +70,4 @@ module Middleman::Extensions
   
   # Register the extension
   register :directory_indexes, DirectoryIndexes
-end
\ No newline at end of file
+end
diff --git a/middleman-core/lib/middleman-core/sitemap/page.rb b/middleman-core/lib/middleman-core/sitemap/page.rb
index 8a8fab81..b14faca7 100644
--- a/middleman-core/lib/middleman-core/sitemap/page.rb
+++ b/middleman-core/lib/middleman-core/sitemap/page.rb
@@ -6,6 +6,8 @@ module Middleman::Sitemap
     # @return [Middleman::Sitemap::Store]
     attr_accessor :store
     
+    # The source path of this page (relative to the source directory,
+    # without template extensions)
     # @return [String]
     attr_accessor :path
     
@@ -41,9 +43,9 @@ module Middleman::Sitemap
     # @return [String]
     def request_path
       if proxy?
-        store.page(proxied_to).path
+        store.page(proxied_to).destination_path
       else
-        path
+        destination_path
       end
     end
     
@@ -185,6 +187,16 @@ module Middleman::Sitemap
     def relative_path
       self.source_file ? self.source_file.sub(app.source_dir, '') : nil
     end
+
+    # Get the destination path, relative to the build directory.
+    # This path can be affected by proxy callbacks.
+    # @return [String]
+    def destination_path
+      # TODO: memoize this value
+      store.reroute_callbacks.inject(self.path) do |destination, callback|
+        callback.call(destination, self)
+      end
+    end
     
     # This page's frontmatter
     # @return [Hash, nil]
@@ -263,4 +275,4 @@ module Middleman::Sitemap
       store.app
     end
   end
-end
\ No newline at end of file
+end
diff --git a/middleman-core/lib/middleman-core/sitemap/store.rb b/middleman-core/lib/middleman-core/sitemap/store.rb
index 9071f1b6..b14dac67 100644
--- a/middleman-core/lib/middleman-core/sitemap/store.rb
+++ b/middleman-core/lib/middleman-core/sitemap/store.rb
@@ -2,6 +2,11 @@
 module Middleman::Sitemap
   
   # The Store class
+  #
+  # The Store manages a collection of Page objects, which represent
+  # individual items in the sitemap. Pages are indexed by "source path",
+  # which is the path relative to the source directory, minus any template
+  # extensions. All "path" parameters used in this class are source paths.
   class Store
     
     # @return [Middleman::Base]
@@ -16,24 +21,25 @@ module Middleman::Sitemap
       @ignored_globs     = []
       @ignored_regexes   = []
       @ignored_callbacks = []
+      @reroute_callbacks   = []
     end
     
     # Check to see if we know about a specific path
     # @param [String] path
     # @return [Boolean]
     def exists?(path)
-      @pages.has_key?(path.sub(/^\//, ""))
+      @pages.has_key?(normalize_path(path))
     end
     
     # Ignore a path or add an ignore callback
-    # @param [String, Regexp] path
+    # @param [String, Regexp] path, path glob expression, or path regex
     # @return [void]
     def ignore(path=nil, &block)
       if !path.nil? && path.include?("*")
-        path_clean = path.sub(/^\//, "")
+        path_clean = normalize_path(path)
         @ignored_globs << path_clean unless @ignored_globs.include?(path_clean)
       elsif path.is_a? String
-        path_clean = path.sub(/^\//, "")
+        path_clean = normalize_path(path)
         @ignored_paths << path_clean unless @ignored_paths.include?(path_clean)
       elsif path.is_a? Regexp
         @ignored_regexes << path unless @ignored_regexes.include?(path)
@@ -42,33 +48,52 @@ module Middleman::Sitemap
       end
     end
     
+    # Add a callback that will be run with each page's destination path
+    # and can produce a new destination path or pass through the old one.
+    # @return [void]
+    def reroute(&block)
+      @reroute_callbacks << block if block_given?
+    end
+
+    # The list of reroute callbacks
+    # @return [Array<Proc>]
+    def reroute_callbacks
+      @reroute_callbacks
+    end
+
     # Setup a proxy from a path to a target
     # @param [String] path
     # @param [String] target
     # @return [void]
     def proxy(path, target)
-      page(path) { proxy_to(target.sub(%r{^/}, "")) }
+      page(path).proxy_to(normalize_path(target))
       app.cache.remove(:proxied_paths)
     end
     
     # Get a page instance for a given path
     # @param [String] path
     # @return [Middleman::Sitemap::Page]
-    def page(path, &block)
-      path = path.sub(/^\//, "").gsub("%20", " ")
-      @pages[path] = ::Middleman::Sitemap::Page.new(self, path) unless @pages.has_key?(path)
-      @pages[path].instance_exec(&block) if block_given?
-      @pages[path]
+    def page(path)
+      path = normalize_path(path)
+      @pages.fetch(path) { @pages[path] = ::Middleman::Sitemap::Page.new(self, path) }
+    end
+
+    # Find a page given its destination path
+    def page_by_destination(destination_path)
+      # TODO: memoize this
+      destination_path = normalize_path(destination_path)
+      @pages.values.find {|p| p.destination_path == destination_path }
     end
     
     # Loop over known pages
+    # @yield [path, page]
     # @return [void]
-    def each(&block)
+    def each
       @pages.each do |k, v|
         yield k, v
       end
     end
-    
+
     # Get all known paths
     # @return [Array<String>]
     def all_paths
@@ -79,15 +104,15 @@ module Middleman::Sitemap
     # @param [String] path
     # @return [Boolean]
     def ignored?(path)
-      path_clean = path.sub(/^\//, "")
-      
-      # $stderr.puts path_clean, @ignored_globs, @ignored_paths
+      path_clean = normalize_path(path)
       
       return true if @ignored_paths.include?(path_clean)
       return true if @ignored_globs.any? { |g| File.fnmatch(g, path_clean) }
       return true if @ignored_regexes.any? { |r| r.match(path_clean) }
       return true if @ignored_callbacks.any? { |b| b.call(path_clean) }
-      
+
+      # TODO: We should also check ignored_sitemap_matchers here
+
       false
     end
     
@@ -101,7 +126,7 @@ module Middleman::Sitemap
     # @param [String] path
     # @return [Boolean]
     def generic?(path)
-      generic_paths.include?(path.sub(/^\//, ""))
+      generic_paths.include?(normalize_path(path))
     end
     
     # Get a list of generic paths
@@ -116,7 +141,7 @@ module Middleman::Sitemap
     # @param [String] path
     # @return [Boolean]
     def proxied?(path)
-      proxied_paths.include?(path.sub(/^\//, ""))
+      proxied_paths.include?(normalize_path(path))
     end
     
     # Get a list of proxied paths
@@ -134,7 +159,7 @@ module Middleman::Sitemap
       path = file_to_path(file)
       return false unless path
       
-      path = path.sub(/^\//, "")
+      path = normalize_path(path)
       if @pages.has_key?(path)
         page(path).delete()
         @pages.delete(path)
@@ -189,7 +214,7 @@ module Middleman::Sitemap
   
     # Get a path without templating extensions
     # @param [String] file
-    # @param [String]
+    # @return [String]
     def extensionless_path(file)
       app.cache.fetch(:extensionless_path, file) do
         path = file.dup
@@ -206,5 +231,12 @@ module Middleman::Sitemap
         path
       end
     end
+
+    # Normalize a path to not include a leading slash
+    # @param [String] path
+    # @return [String]
+    def normalize_path(path)
+      path.sub(/^\//, "").gsub("%20", " ")
+    end
   end
 end