diff --git a/lib/compass/configuration.rb b/lib/compass/configuration.rb
index ac4aaf7f..c6ca3e6a 100644
--- a/lib/compass/configuration.rb
+++ b/lib/compass/configuration.rb
@@ -41,6 +41,6 @@ module Compass
   end
 end
 
-['adapters', 'comments', 'defaults', 'helpers', 'inheritance', 'serialization', 'data'].each do |lib|
+['adapters', 'comments', 'defaults', 'helpers', 'inheritance', 'serialization', 'paths', 'data'].each do |lib|
   require "compass/configuration/#{lib}"
 end
diff --git a/lib/compass/configuration/data.rb b/lib/compass/configuration/data.rb
index 6b0db638..abdb82ff 100644
--- a/lib/compass/configuration/data.rb
+++ b/lib/compass/configuration/data.rb
@@ -22,10 +22,13 @@ module Compass
       include Compass::Configuration::Inheritance
       include Compass::Configuration::Serialization
       include Compass::Configuration::Adapters
+      extend  Compass::Configuration::Paths
 
       inherited_accessor *ATTRIBUTES
       inherited_accessor :required_libraries #XXX we should make this array add up cumulatively.
 
+      strip_trailing_separator *ATTRIBUTES.select{|a| a.to_s =~ /dir|path/}
+
       def initialize(name, attr_hash = nil)
         raise "I need a name!" unless name
         @name = name
diff --git a/lib/compass/configuration/paths.rb b/lib/compass/configuration/paths.rb
new file mode 100644
index 00000000..01d9cd92
--- /dev/null
+++ b/lib/compass/configuration/paths.rb
@@ -0,0 +1,19 @@
+module Compass::Configuration::Paths
+
+  TRAILING_SEPARATOR = %r{.(/|#{Regexp.escape(File::SEPARATOR)})$}
+
+  def strip_trailing_separator(*attributes)
+    attributes.each do |attr|
+      alias_method "#{attr}_with_trailing_separator".to_sym, attr
+      class_eval %Q{
+        def #{attr}                                # def css_dir
+          path = #{attr}_with_trailing_separator   #   path = css_dir_with_trailing_separator
+          if path =~ TRAILING_SEPARATOR            #   if path =~ TRAILING_SEPARATOR
+            path = path[0..-($1.length+1)]         #     path = path[0..-($1.length+1)]
+          end                                      #   end
+          path                                     #   path
+        end                                        # end
+      }
+    end
+  end
+end
diff --git a/test/configuration_test.rb b/test/configuration_test.rb
index c53a625b..d13c528e 100644
--- a/test/configuration_test.rb
+++ b/test/configuration_test.rb
@@ -120,4 +120,29 @@ EXPECTED
       assert_equal expected_serialization, Compass.configuration.serialize
     end
 
+  def test_strip_trailing_directory_separators
+    contents = StringIO.new(<<-CONFIG)
+      css_dir = "css/"
+      sass_dir = "sass/"
+      images_dir = "images/"
+      javascripts_dir = "js/"
+      fonts_dir = "fonts/"
+      extensions_dir = "extensions/"
+      css_path = "css/"
+      sass_path = "sass/"
+      images_path = "images/"
+      javascripts_path = "js/"
+      fonts_path = "fonts/"
+      extensions_path = "extensions/"
+    CONFIG
+
+    Compass.add_configuration(contents, "test_strip_trailing_directory_separators")
+
+    assert_equal "css", Compass.configuration.css_dir
+    assert_equal "sass", Compass.configuration.sass_dir
+    assert_equal "images", Compass.configuration.images_dir
+    assert_equal "js", Compass.configuration.javascripts_dir
+    assert_equal "fonts", Compass.configuration.fonts_dir
+    assert_equal "extensions", Compass.configuration.extensions_dir
+  end
 end