diff --git a/beets/importer.py b/beets/importer.py
index cf60b791a..a499ec792 100644
--- a/beets/importer.py
+++ b/beets/importer.py
@@ -522,9 +522,7 @@ def apply_choices(config):
 
         # Move/copy files.
         items = task.items if task.is_album else [task.item]
-        if config.copy and config.delete:
-            task.old_paths = [os.path.realpath(syspath(item.path))
-                              for item in items]
+        task.old_paths = [item.path for item in items]
         for item in items:
             if config.copy:
                 item.move(lib, True, task.is_album)
@@ -547,9 +545,9 @@ def apply_choices(config):
             # Remove old entries if we're re-importing old items. Old
             # album structures are automatically cleaned up when the
             # last item is removed.
-            for item in items:
+            for item, old_path in zip(items, task.old_paths):
                 dup_items = list(lib.items(
-                                    library.MatchQuery('path', item.path)
+                                    library.MatchQuery('path', old_path)
                             ))
                 for dup_item in dup_items:
                     if dup_item.id != item.id:
diff --git a/test/test_importer.py b/test/test_importer.py
index 15173badc..0c3dd5ac4 100644
--- a/test/test_importer.py
+++ b/test/test_importer.py
@@ -285,7 +285,7 @@ class AsIsApplyTest(unittest.TestCase):
         self.assertFalse(alb.comp)
         self.assertEqual(alb.albumartist, self.items[2].artist)
 
-class ApplyExistingItemsTest(unittest.TestCase):
+class ApplyExistingItemsTest(unittest.TestCase, _common.ExtraAsserts):
     def setUp(self):
         self.libdir = os.path.join(_common.RSRC, 'testlibdir')
         os.mkdir(self.libdir)
@@ -343,6 +343,36 @@ class ApplyExistingItemsTest(unittest.TestCase):
         # Should not be duplicated.
         self.assertEqual(len(list(self.lib.items())), 1)
 
+    def test_apply_existing_item_new_metadata_does_not_duplicate(self):
+        # We want to copy the item to a new location.
+        self.config.copy = True
+
+        # Import with existing metadata.
+        self._apply_asis([self.i])
+
+        # Import again with new metadata.
+        item = self.lib.items().next()
+        new_item = library.Item.from_path(item.path)
+        new_item.title = 'differentTitle'
+        self._apply_asis([new_item])
+
+        # Should not be duplicated.
+        self.assertEqual(len(list(self.lib.items())), 1)
+        self.assertEqual(len(list(self.lib.albums())), 1)
+
+    def test_apply_existing_item_new_metadata_moves_files(self):
+        # As above, import with old metadata and then reimport with new.
+        self.config.copy = True
+        self._apply_asis([self.i])
+        item = self.lib.items().next()
+        new_item = library.Item.from_path(item.path)
+        new_item.title = 'differentTitle'
+        self._apply_asis([new_item])
+
+        item = self.lib.items().next()
+        self.assertTrue('differentTitle' in item.path)
+        self.assertExists(item.path)
+
 class InferAlbumDataTest(unittest.TestCase):
     def setUp(self):
         i1 = _common.item()