diff --git a/src/pretix/plugins/sendmail/models.py b/src/pretix/plugins/sendmail/models.py
index eebb69d290..7f979e94a3 100644
--- a/src/pretix/plugins/sendmail/models.py
+++ b/src/pretix/plugins/sendmail/models.py
@@ -23,7 +23,7 @@ from datetime import datetime, time, timedelta
 
 from dateutil.tz import datetime_exists
 from django.db import models
-from django.db.models import Exists, OuterRef, Q
+from django.db.models import Exists, F, OuterRef, Q
 from django.utils import timezone
 from django.utils.formats import date_format
 from django.utils.timezone import make_aware, now
@@ -166,7 +166,8 @@ class ScheduledMail(models.Model):
 
         for o in orders:
             with language(o.locale, e.settings.region):
-                positions = list(o.positions.all())
+                positions = list(o.positions.all().order_by(F("addon_to_id").asc(
+                    nulls_first=True)))  # ordered to make sure we always handle parent order positions before add-ons
                 o_sent = False
 
                 try: