diff --git a/lib/sass/engine.rb b/lib/sass/engine.rb
index cfedab31..91e9717f 100644
--- a/lib/sass/engine.rb
+++ b/lib/sass/engine.rb
@@ -215,6 +215,7 @@ END
       end
 
       node.line = @line
+      node.filename = @options[:filename]
 
       if node.is_a? Tree::CommentNode
         while has_children
@@ -410,7 +411,7 @@ END
           File.open(filename) do |file|
             new_options = @options.dup
             new_options[:filename] = filename
-            engine = Sass::Engine.new(file.read, @options)
+            engine = Sass::Engine.new(file.read, new_options)
           end
 
           engine.constants.merge! @constants
@@ -422,10 +423,7 @@ END
             err.add_backtrace_entry(filename)
             raise err
           end
-          root.children.each do |child|
-            child.filename = filename
-            nodes << child
-          end
+          nodes += root.children
           @constants = engine.constants
           @mixins = engine.mixins
         end
diff --git a/lib/sass/plugin.rb b/lib/sass/plugin.rb
index 7c0dd984..11176f2d 100644
--- a/lib/sass/plugin.rb
+++ b/lib/sass/plugin.rb
@@ -1,4 +1,5 @@
 require 'sass/engine'
+require 'pathname'
 
 module Sass
   # This module contains methods to aid in using Sass
@@ -54,6 +55,7 @@ module Sass
 
             filename = template_filename(name)
             l_options = @@options.dup
+            l_options[:css_filename] = css
             l_options[:filename] = filename
             l_options[:load_paths] = load_paths
             engine = Engine.new(File.read(filename), l_options)
diff --git a/lib/sass/tree/rule_node.rb b/lib/sass/tree/rule_node.rb
index 49cf1195..1711958b 100644
--- a/lib/sass/tree/rule_node.rb
+++ b/lib/sass/tree/rule_node.rb
@@ -66,7 +66,14 @@ module Sass::Tree
         old_spaces = '  ' * (tabs - 1)
         spaces = '  ' * tabs
         if @options[:line_comments] && @style != :compressed
-          to_return << "/* line #{line} */\n"
+          to_return << "#{old_spaces}/* line #{line}"
+
+          if filename && @options[:css_filename]
+            relative_filename = Pathname.new(filename).relative_path_from(Pathname.new(File.dirname(@options[:css_filename]))).to_s
+            to_return << ", #{relative_filename}"
+          end
+
+          to_return << " */\n"
         end
 
         if @style == :compact
diff --git a/test/sass/engine_test.rb b/test/sass/engine_test.rb
index 35091735..0447bc32 100755
--- a/test/sass/engine_test.rb
+++ b/test/sass/engine_test.rb
@@ -298,6 +298,10 @@ bip, skip
 SASS
   end
 
+  def test_line_annotations_with_filename
+    renders_correctly "line_numbers", :line_comments => true, :load_paths => [File.dirname(__FILE__) + "/templates"]
+  end
+
   def test_empty_first_line
     assert_equal("#a {\n  b: c; }\n", render("#a\n\n  b: c"))
   end
@@ -349,13 +353,19 @@ SASS
   def renders_correctly(name, options={})
     sass_file  = load_file(name, "sass")
     css_file   = load_file(name, "css")
+    options[:filename] ||= filename(name, "sass")
+    options[:css_filename] ||= filename(name, "css")
     css_result = Sass::Engine.new(sass_file, options).render
     assert_equal css_file, css_result
   end
 
   def load_file(name, type = "sass")
     @result = ''
-    File.new(File.dirname(__FILE__) + "/#{type == 'sass' ? 'templates' : 'results'}/#{name}.#{type}").each_line { |l| @result += l }
+    File.new(filename(name, type)).each_line { |l| @result += l }
     @result
   end
+
+  def filename(name, type)
+    File.dirname(__FILE__) + "/#{type == 'sass' ? 'templates' : 'results'}/#{name}.#{type}"
+  end
 end
diff --git a/test/sass/results/line_numbers.css b/test/sass/results/line_numbers.css
new file mode 100644
index 00000000..3c657f93
--- /dev/null
+++ b/test/sass/results/line_numbers.css
@@ -0,0 +1,49 @@
+/* line 1, ../templates/line_numbers.sass */
+foo {
+  bar: baz; }
+
+/* line 6, ../templates/importee.sass */
+imported {
+  otherconst: 12;
+  myconst: goodbye; }
+  /* line 5, ../templates/line_numbers.sass */
+  imported squggle {
+    blat: bang; }
+
+/* line 3, ../templates/basic.sass */
+body {
+  font: Arial;
+  background: blue; }
+
+/* line 7, ../templates/basic.sass */
+#page {
+  width: 700px;
+  height: 100; }
+  /* line 10, ../templates/basic.sass */
+  #page #header {
+    height: 300px; }
+    /* line 12, ../templates/basic.sass */
+    #page #header h1 {
+      font-size: 50px;
+      color: blue; }
+
+/* line 18, ../templates/basic.sass */
+#content.user.show #container.top #column.left {
+  width: 100px; }
+/* line 20, ../templates/basic.sass */
+#content.user.show #container.top #column.right {
+  width: 600px; }
+/* line 22, ../templates/basic.sass */
+#content.user.show #container.bottom {
+  background: brown; }
+
+/* line 13, ../templates/importee.sass */
+midrule {
+  inthe: middle; }
+
+/* line 12, ../templates/line_numbers.sass */
+umph {
+  foo: bar; }
+  /* line 18, ../templates/importee.sass */
+  umph baz {
+    blat: bang; }
diff --git a/test/sass/templates/importee.sass b/test/sass/templates/importee.sass
index 4c8492ab..aa2a0261 100644
--- a/test/sass/templates/importee.sass
+++ b/test/sass/templates/importee.sass
@@ -11,4 +11,9 @@ imported
 @import basic
 
 midrule
-  :inthe middle
\ No newline at end of file
+  :inthe middle
+
+=crazymixin
+  foo: bar
+  baz
+    blat: bang
diff --git a/test/sass/templates/line_numbers.sass b/test/sass/templates/line_numbers.sass
new file mode 100644
index 00000000..c554d581
--- /dev/null
+++ b/test/sass/templates/line_numbers.sass
@@ -0,0 +1,13 @@
+foo
+  bar: baz
+
+=premixin
+  squggle
+    blat: bang
+
+!preconst = 12
+
+@import importee
+
+umph
+  +crazymixin
\ No newline at end of file