diff --git a/modules/simpletest/tests/upgrade/drupal-6.upload.database.php b/modules/simpletest/tests/upgrade/drupal-6.upload.database.php
index 50025b4..ff3f382 100644
--- a/modules/simpletest/tests/upgrade/drupal-6.upload.database.php
+++ b/modules/simpletest/tests/upgrade/drupal-6.upload.database.php
@@ -127,8 +127,8 @@ db_insert('files')->fields(array(
   'status' => '1',
   'timestamp' => '1285708958',
 ))
-// Under some configurations we end up having two fids with the same filepath,
-//see https://www.drupal.org/node/1260938.
+// On some Drupal 6 sites, more than one file can have the same filepath. See
+// https://www.drupal.org/node/1260938.
 ->values(array(
   'fid' => '12',
   'uid' => '1',
@@ -149,6 +149,16 @@ db_insert('files')->fields(array(
   'status' => '1',
   'timestamp' => '1285708958',
 ))
+->values(array(
+  'fid' => '14',
+  'uid' => '1',
+  'filename' => 'duplicate-name.png',
+  'filepath' => 'sites/default/files/duplicate-name.png',
+  'filemime' => 'image/png',
+  'filesize' => '314',
+  'status' => '1',
+  'timestamp' => '1285708958',
+))
 ->execute();
 
 db_insert('node')->fields(array(
@@ -309,8 +319,8 @@ db_insert('node_revisions')->fields(array(
   'vid' => '55',
   'uid' => '1',
   'title' => 'node title 41 revision 55',
-  'body' => "Attachments:\r\nduplicate-name.png",
-  'teaser' => "Attachments:\r\nduplicate-name.png",
+  'body' => "Attachments:\r\nduplicate-name.png\r\nduplicate-name.png",
+  'teaser' => "Attachments:\r\nduplicate-name.png\r\nduplicate-name.png",
   'log' => '',
   'timestamp' => '1285709012',
   'format' => '1',
@@ -488,7 +498,15 @@ db_insert('upload')->fields(array(
   'fid' => '13',
   'nid' => '41',
   'vid' => '55',
-  'description' => 'duplicate-name.png',
+  'description' => 'first description',
+  'list' => '0',
+  'weight' => '0',
+))
+->values(array(
+  'fid' => '14',
+  'nid' => '41',
+  'vid' => '55',
+  'description' => 'second description',
   'list' => '1',
   'weight' => '0',
 ))
diff --git a/modules/simpletest/tests/upgrade/upgrade.upload.test b/modules/simpletest/tests/upgrade/upgrade.upload.test
index b43c367..9b6ed89 100644
--- a/modules/simpletest/tests/upgrade/upgrade.upload.test
+++ b/modules/simpletest/tests/upgrade/upgrade.upload.test
@@ -74,13 +74,20 @@ class UploadUpgradePathTestCase extends UpgradePathTestCase {
     // Ensure that duplicate filepaths are reduced.
     $node0 = node_load(41, 54);
     $node1 = node_load(41, 55);
-    // Ensure that both revisions point to the same FID.
+    // Ensure that both revisions point to the same file ID.
     $items0 = field_get_items('node', $node0, 'upload');
     $this->assertEqual(count($items0), 1);
     $items1 = field_get_items('node', $node1, 'upload');
-    $this->assertEqual(count($items1), 1);
+    $this->assertEqual(count($items1), 2);
     $this->assertEqual($items0[0]['fid'], $items1[0]['fid']);
-
+    $this->assertEqual($items0[0]['fid'], $items1[1]['fid']);
+    // The revision with more than one reference to the same file should retain
+    // the original settings for each reference.
+    $this->assertEqual($items1[0]['description'], 'first description');
+    $this->assertEqual($items1[0]['display'], 0);
+    $this->assertEqual($items1[1]['description'], 'second description');
+    $this->assertEqual($items1[1]['display'], 1);
+    // No duplicate files should remain on the Drupal 7 site.
     $this->assertEqual(0, db_query("SELECT COUNT(*) FROM {file_managed} GROUP BY uri HAVING COUNT(fid) > 1")->fetchField());
 
     // Make sure the file settings were properly migrated.