diff --git a/Library/Homebrew/keg.rb b/Library/Homebrew/keg.rb
index 93e8b78573..6218668d65 100644
--- a/Library/Homebrew/keg.rb
+++ b/Library/Homebrew/keg.rb
@@ -37,6 +37,8 @@ class Keg < Pathname
     # of files and directories linked
     $n=$d=0
 
+    dirs = []
+
     TOP_LEVEL_DIRECTORIES.map{ |d| self/d }.each do |dir|
       next unless dir.exist?
       dir.find do |src|
@@ -44,6 +46,8 @@ class Keg < Pathname
         dst = HOMEBREW_PREFIX + src.relative_path_from(self)
         dst.extend(ObserverPathnameExtension)
 
+        dirs << dst if dst.directory? && !dst.symlink?
+
         # check whether the file to be unlinked is from the current keg first
         if !dst.symlink? || !dst.exist? || src != dst.resolved_path
           next
@@ -51,11 +55,13 @@ class Keg < Pathname
 
         dst.uninstall_info if dst.to_s =~ INFOFILE_RX and ENV['HOMEBREW_KEEP_INFO']
         dst.unlink
-        dst.parent.extend(ObserverPathnameExtension).rmdir_if_possible
         Find.prune if src.directory?
       end
     end
     linked_keg_record.unlink if linked_keg_record.symlink?
+
+    dirs.reverse_each(&:rmdir_if_possible)
+
     $n+$d
   end
 
diff --git a/Library/Homebrew/test/test_keg.rb b/Library/Homebrew/test/test_keg.rb
index de6ffa0d84..d9cce89fa3 100644
--- a/Library/Homebrew/test/test_keg.rb
+++ b/Library/Homebrew/test/test_keg.rb
@@ -85,17 +85,17 @@ class LinkTests < Test::Unit::TestCase
     assert_equal "#{HOMEBREW_PREFIX}/bin/helloworld\n", $stdout.string
   end
 
-  def test_unlink_prunes_empty_toplevel_directories_fails
+  def test_unlink_prunes_empty_toplevel_directories
     mkpath HOMEBREW_PREFIX/"lib/foo/bar"
     mkpath @keg/"lib/foo/bar"
     touch @keg/"lib/foo/bar/file1"
 
     @keg.unlink
 
-    assert File.directory?(HOMEBREW_PREFIX/"lib/foo")
+    assert !File.directory?(HOMEBREW_PREFIX/"lib/foo")
   end
 
-  def test_unlink_ignores_DS_Store_when_pruning_empty_dirs_fails
+  def test_unlink_ignores_DS_Store_when_pruning_empty_dirs
     mkpath HOMEBREW_PREFIX/"lib/foo/bar"
     touch HOMEBREW_PREFIX/"lib/foo/.DS_Store"
     mkpath @keg/"lib/foo/bar"
@@ -103,8 +103,8 @@ class LinkTests < Test::Unit::TestCase
 
     @keg.unlink
 
-    assert File.directory?(HOMEBREW_PREFIX/"lib/foo")
-    assert File.exist?(HOMEBREW_PREFIX/"lib/foo/.DS_Store")
+    assert !File.directory?(HOMEBREW_PREFIX/"lib/foo")
+    assert !File.exist?(HOMEBREW_PREFIX/"lib/foo/.DS_Store")
   end
 
   def teardown