this is a little on the nose, but should get to the meat of it

multi-meta-under-combined-meta-test.patch

diff --git a/test/unit/obj/test_diskfile.py b/test/unit/obj/test_diskfile.py
index c602912..a0d4da1 100644
--- a/test/unit/obj/test_diskfile.py
+++ b/test/unit/obj/test_diskfile.py
@@ -2801,6 +2801,28 @@ class DiskFileMixin(BaseDiskFileTestMixin):
         self.assertTrue(exp_name in set(dl),
                         'Expected file %s not found in %s' % (exp_name, dl))
 
+    def test_cleanup_older_metadata_when_combined_older_content_type(self):
+        # if metadata has content-type then its time should be in file name
+        ts_iter = make_timestamp_iter()
+        df = self._create_test_file('1234567890', timestamp=ts_iter.next())
+        file_count = len(os.listdir(df._datadir))
+        timestamp = ts_iter.next()
+        timestamp2 = ts_iter.next()
+        metadata = {'X-Timestamp': timestamp2.internal,
+                    'X-Object-Meta-test': 'data'}
+        df.write_metadata(metadata)
+        metadata = {'X-Timestamp': timestamp2.internal,
+                    'X-Object-Meta-test': 'data',
+                    'Content-Type': 'foo',
+                    'Content-Type-Timestamp': timestamp.internal}
+        df.write_metadata(metadata)
+        dl = df.manager.hash_cleanup_listdir(df._datadir)
+        self.assertEqual(len(dl), file_count + 1, dl)
+        exp_name = '%s-%x.meta' % (timestamp2.internal,
+                                   timestamp2.raw - timestamp.raw)
+        self.assertTrue(exp_name in set(dl),
+                        'Expected file %s not found in %s' % (exp_name, dl))
+
     def test_write_metadata_no_xattr(self):
         timestamp = Timestamp(time()).internal
         metadata = {'X-Timestamp': timestamp, 'X-Object-Meta-test': 'data'}