diff --git a/zerver/lib/actions.py b/zerver/lib/actions.py
index 9b08a49808..1620e2e1c6 100644
--- a/zerver/lib/actions.py
+++ b/zerver/lib/actions.py
@@ -2438,6 +2438,10 @@ def do_update_message(user_profile, message_id, subject, propagate_mode, content
         event["content"] = content
         event["rendered_content"] = rendered_content
 
+        prev_content = edit_history_event['prev_content']
+        if Message.content_has_attachment(prev_content) or Message.content_has_attachment(message.content):
+            check_attachment_reference_change(prev_content, message)
+
     if subject is not None:
         orig_subject = message.subject
         subject = truncate_topic(subject)
@@ -3302,3 +3306,32 @@ def do_delete_old_unclaimed_attachments(weeks_ago):
     for attachment in old_unclaimed_attachments:
         delete_message_image(attachment.path_id)
         attachment.delete()
+
+def check_attachment_reference_change(prev_content, message):
+    new_content = message.content
+    attachment_url_re = re.compile(u'[/\-]user[\-_]uploads[/\.-].*?(?=[ )]|\Z)')
+    prev_attachments = set(attachment_url_re.findall(prev_content))
+    new_attachments = set(attachment_url_re.findall(new_content))
+
+    to_remove = list(prev_attachments - new_attachments)
+    path_ids = []
+    for url in to_remove:
+        path_id = re.sub(u'[/\-]user[\-_]uploads[/\.-]', u'', url)
+        # Remove any extra '.' after file extension. These are probably added by the user
+        path_id = re.sub(u'[.]+$', u'', path_id, re.M)
+        path_ids.append(path_id)
+
+    attachments_to_update = Attachment.objects.filter(path_id__in=path_ids).select_for_update()
+    for attachment in attachments_to_update:
+        try:
+            attachment = Attachment.objects.get(path_id=path_id)
+            attachment.messages.remove(message)
+            attachment.save()
+        except Attachment.DoesNotExist:
+            # The entry for this attachment does not exist. Just ignore.
+            pass
+
+    to_add = list(new_attachments - prev_attachments)
+    if len(to_add) > 1:
+        do_claim_attachments(message)
+
diff --git a/zerver/tests/test_upload.py b/zerver/tests/test_upload.py
index 6a2646cd88..3994411b1e 100644
--- a/zerver/tests/test_upload.py
+++ b/zerver/tests/test_upload.py
@@ -11,7 +11,7 @@ from zerver.lib.upload import sanitize_name, S3UploadBackend, \
     upload_message_image, delete_message_image, LocalUploadBackend
 import zerver.lib.upload
 from zerver.models import Attachment, Recipient, get_user_profile_by_email, \
-    get_old_unclaimed_attachments
+    get_old_unclaimed_attachments, Message
 from zerver.lib.actions import do_delete_old_unclaimed_attachments
 
 import ujson
@@ -189,6 +189,52 @@ class FileUploadTest(AuthedTestCase):
 
         self.assertEquals(Attachment.objects.get(path_id=d1_path_id).messages.count(), 2)
 
+    def test_check_attachment_reference_update(self):
+        f1 = StringIO("file1")
+        f1.name = "file1.txt"
+        f2 = StringIO("file2")
+        f2.name = "file2.txt"
+        f3 = StringIO("file3")
+        f3.name = "file3.txt"
+
+        self.login("hamlet@zulip.com")
+        result = self.client.post("/json/upload_file", {'file': f1})
+        json = ujson.loads(result.content)
+        uri = json["uri"]
+        f1_path_id = re.sub('/user_uploads/', '', uri)
+
+        result = self.client.post("/json/upload_file", {'file': f2})
+        json = ujson.loads(result.content)
+        uri = json["uri"]
+        f2_path_id = re.sub('/user_uploads/', '', uri)
+
+        self.subscribe_to_stream("hamlet@zulip.com", "test")
+        body = ("[f1.txt](http://localhost:9991/user_uploads/" + f1_path_id + ")"
+               "[f2.txt](http://localhost:9991/user_uploads/" + f2_path_id + ")")
+        msg_id = self.send_message("hamlet@zulip.com", "test", Recipient.STREAM, body, "test")
+
+        result = self.client.post("/json/upload_file", {'file': f3})
+        json = ujson.loads(result.content)
+        uri = json["uri"]
+        f3_path_id = re.sub('/user_uploads/', '', uri)
+
+        new_body = ("[f3.txt](http://localhost:9991/user_uploads/" + f3_path_id + ")"
+                   "[f2.txt](http://localhost:9991/user_uploads/" + f2_path_id + ")")
+        result = self.client.post("/json/update_message", {
+            'message_id': msg_id,
+            'content': new_body
+        })
+        self.assert_json_success(result)
+
+        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)
+
+        self.assertTrue(message not in f1_attachment.messages.all())
+        self.assertTrue(message in f2_attachment.messages.all())
+        self.assertTrue(message in f3_attachment.messages.all())
+
     def tearDown(self):
         # type: () -> None
         destroy_uploads()