diff --git a/Library/Homebrew/cleaner.rb b/Library/Homebrew/cleaner.rb
index ea5ece779f..3950cd846f 100644
--- a/Library/Homebrew/cleaner.rb
+++ b/Library/Homebrew/cleaner.rb
@@ -55,15 +55,14 @@ class Cleaner
 
   def clean_file path
     perms = 0444
-    case `/usr/bin/file -h '#{path}'`
-    when /Mach-O dynamically linked shared library/
+    if path.dylib?
       # Stripping libraries is causing no end of trouble. Lets just give up,
       # and try to do it manually in instances where it makes sense.
       #strip path, '-SxX'
-    when /Mach-O [^ ]* ?executable/
+    elsif path.mach_o_executable?
       strip path
       perms = 0555
-    when /text executable/
+    elsif path.text_executable?
       perms = 0555
     end
     path.chmod perms
diff --git a/Library/Homebrew/test/test_cleaner.rb b/Library/Homebrew/test/test_cleaner.rb
new file mode 100644
index 0000000000..e9e9c96ef6
--- /dev/null
+++ b/Library/Homebrew/test/test_cleaner.rb
@@ -0,0 +1,38 @@
+require 'testing_env'
+
+require 'extend/ARGV' # needs to be after test/unit to avoid conflict with OptionsParser
+ARGV.extend(HomebrewArgvExtension)
+
+require 'cleaner'
+
+class CleanerTestBall < Formula
+  def initialize name=nil
+    @url="file:///#{TEST_FOLDER}/tarballs/testball-0.1.tbz"
+    @homepage = 'http://example.com/'
+    super "cleanertestball"
+  end
+
+  def install
+    TEST_FOLDER.cd do
+      bin.mkpath
+      lib.mkpath
+      cp 'mach/a.out', bin
+      cp 'mach/fat.dylib', lib
+      cp 'mach/x86_64.dylib', lib
+      cp 'mach/i386.dylib', lib
+    end
+  end
+end
+
+class CleanerTests < Test::Unit::TestCase
+  def test_clean_file
+    f = CleanerTestBall.new
+    nostdout { f.brew { f.install } }
+
+    assert_nothing_raised { Cleaner.new f }
+    assert_equal 0100555, (f.bin/'a.out').stat.mode
+    assert_equal 0100444, (f.lib/'fat.dylib').stat.mode
+    assert_equal 0100444, (f.lib/'x86_64.dylib').stat.mode
+    assert_equal 0100444, (f.lib/'i386.dylib').stat.mode
+  end
+end