diff --git a/doc/upgrade.rst b/doc/upgrade.rst
index 1a0675db5..bec3a4c56 100644
--- a/doc/upgrade.rst
+++ b/doc/upgrade.rst
@@ -144,6 +144,17 @@ Version 2.3.0
    new migrations **AFTER** the following instructions. If you don't,
    you'll get into trouble...
 
+Pre update
+----------
+
+Before your start upgrading modoboa, run the following commands from
+your virtual environment:
+
+.. sourcecode:: bash
+
+   > python manage.py modo repair
+   > python manage.py rename_app modoboa_postfix_autoreply postfix_autoreply
+
 Required changes to :file:`settings.py`
 ---------------------------------------
 
@@ -301,16 +312,6 @@ SORBS DNS
          bl.spameatingmonkey.net=127.0.0.2*2
          bl.spamcop.net=127.0.0.2
 
-
-Post update
------------
-
-After upgrading modoboa, run the following commands from your virtual environment:
-
-.. sourcecode:: bash
-
-   > python manage.py rename_app modoboa_postfix_autoreply postfix_autoreply
-
 Version 2.2.3
 =============
 
diff --git a/modoboa/admin/management/commands/subcommands/_repair.py b/modoboa/admin/management/commands/subcommands/_repair.py
index 5a921d6ce..27a5f2cf6 100644
--- a/modoboa/admin/management/commands/subcommands/_repair.py
+++ b/modoboa/admin/management/commands/subcommands/_repair.py
@@ -4,6 +4,9 @@ from django.conf import settings
 from django.core.management.base import BaseCommand
 from django.utils.encoding import smart_str
 
+from django.contrib.auth.models import Permission
+from django.contrib.contenttypes.models import ContentType
+
 from modoboa.admin import models
 from modoboa.core.models import User
 from modoboa.lib.permissions import get_object_owner, grant_access_to_object
@@ -89,6 +92,15 @@ def sometimes_mailbox_have_no_alias(**options):
         )
 
 
+@known_problem
+def postfix_autoreply_old_contenttypes(**options):
+    """Sometime old postfix autoreply contenttypes might be present."""
+    for ct in ContentType.objects.filter(app_label="postfix_autoreply"):
+        result = Permission.objects.filter(content_type=ct).delete()
+        ct.delete()
+        log(f"Removed content type {ct.name} and {result[0]} associated permssions")
+
+
 class Repair(BaseCommand):
     """Command class."""