diff --git a/test/rsrc/unicode_path_sep.mp3 b/test/rsrc/unicode_path_sep.mp3
new file mode 100644
index 000000000..fa543b7fb
Binary files /dev/null and b/test/rsrc/unicode_path_sep.mp3 differ
diff --git a/test/test_library.py b/test/test_library.py
index 26c78c99d..a2f399593 100644
--- a/test/test_library.py
+++ b/test/test_library.py
@@ -416,11 +416,11 @@ class DestinationTest(_common.TestCase):
 
     def test_asciify_and_replace(self):
         config['asciify_paths'] = True
-        self.lib.replacements = [(re.compile(u'"'), u'q')]
+        self.lib.replacements = [(re.compile(u'"'), u'q'), (re.compile(os.path.sep), config['path_sep_replace'].get())]
         self.lib.directory = b'lib'
         self.lib.path_formats = [(u'default', u'$title')]
-        self.i.title = u'\u201c\u00f6\u2014\u00cf\u201d'
-        self.assertEqual(self.i.destination(), np('lib/qo--Iq'))
+        self.i.title = u'\u201c\xa2\u00f6\u2014\u00cf\xbd\u201d'
+        self.assertEqual(self.i.destination(), np('lib/qC_o--I1_2q'))
 
     def test_destination_with_replacements(self):
         self.lib.directory = b'base'