diff --git a/zerver/lib/actions.py b/zerver/lib/actions.py
index dcc15c10d1..e8dc3b10c4 100644
--- a/zerver/lib/actions.py
+++ b/zerver/lib/actions.py
@@ -3368,5 +3368,5 @@ def check_attachment_reference_change(prev_content, message):
             pass
 
     to_add = list(new_attachments - prev_attachments)
-    if len(to_add) > 1:
+    if len(to_add) > 0:
         do_claim_attachments(message)
diff --git a/zerver/tests/test_upload.py b/zerver/tests/test_upload.py
index 1a3bcf08e0..9fe8a7d84c 100644
--- a/zerver/tests/test_upload.py
+++ b/zerver/tests/test_upload.py
@@ -230,7 +230,7 @@ class FileUploadTest(AuthedTestCase):
         message = Message.objects.get(id=msg_id)
         f1_attachment = Attachment.objects.get(path_id=f1_path_id)
         f2_attachment = Attachment.objects.get(path_id=f2_path_id)
-        f3_attachment = Attachment.objects.get(path_id=f2_path_id)
+        f3_attachment = Attachment.objects.get(path_id=f3_path_id)
 
         self.assertTrue(message not in f1_attachment.messages.all())
         self.assertTrue(message in f2_attachment.messages.all())