From ef0d03f6ea5df754c3ca543174ebf591eb6a068b Mon Sep 17 00:00:00 2001
From: Phin Wolkwitz <wolkwitz@rami.io>
Date: Thu, 6 Aug 2026 16:51:14 +0200
Subject: [PATCH] Fix and improve changed mail-rules logic

---
 src/pretix/plugins/sendmail/models.py | 51 +++++++++++++++++++--------
 1 file changed, 36 insertions(+), 15 deletions(-)

diff --git a/src/pretix/plugins/sendmail/models.py b/src/pretix/plugins/sendmail/models.py
index c98a19e1d2..8950e7fde6 100644
--- a/src/pretix/plugins/sendmail/models.py
+++ b/src/pretix/plugins/sendmail/models.py
@@ -187,26 +187,37 @@ class ScheduledMail(models.Model):
                     o_sent = True
 
                 if send_to_attendees:
-                    if not self.rule.all_products:
-                        positions = [p for p in positions if p.item_id in limit_products]
                     if self.subevent_id:
                         positions = [p for p in positions if p.subevent_id == self.subevent_id]
 
+                    parent_op = None
+                    sent_to_parent_positions = set()
                     for p in positions:
+
+                        if p.addon_to_id is None:
+                            parent_op = p
+                        if not self.rule.all_products and p.item_id not in position_ids:
+                            continue
+                        else:
+                            sent_to_parent_positions.add(p.id)
+
                         if p.id in position_ids:
-                            email_to = p.attendee_email if p.attendee_email else None
+                            mail_to_parent = False
 
-                            if not email_to and p.addon_to_id is not None:
-                                try:
-                                    parent_op = o.positions.get(
-                                        id=p.addon_to_id)  # should we rethink the whole positions logic here to reduce DB queries?
-                                except OrderPosition.DoesNotExist:
-                                    raise OrderPosition.DoesNotExist  # this should not happen, but just in case
-                                if parent_op.attendee_email:
-                                    email_to = parent_op.attendee_email
-                                    mail_to_parent = True
+                            # position is an add-on
+                            if p.addon_to_id is not None:
+                                # without attendee-email
+                                if not p.attendee_email:
+                                    if p.addon_to_id in sent_to_parent_positions:
+                                        continue
+                                    elif parent_op.attendee_email:
+                                        sent_to_parent_positions.add(parent_op.id)
+                                        mail_to_parent = True
+                                # with attendee-email but same as parent's and sent to parent
+                                elif parent_op.attendee_email and p.attendee_email == parent_op.attendee_email and parent_op in sent_to_parent_positions:
+                                    continue
 
-                            if email_to != o.email or not o_sent:
+                            if p.attendee_email and (p.attendee_email != o.email or not o_sent):
                                 email_ctx = get_email_context(
                                     event=e,
                                     order=o,
@@ -216,8 +227,18 @@ class ScheduledMail(models.Model):
                                 )
                                 p.send_mail(self.rule.subject, self.rule.template, email_ctx,
                                             attach_ical=self.rule.attach_ical,
-                                            log_entry_type='pretix.plugins.sendmail.rule.order.position.email.sent',
-                                            diff_recipient=email_to if mail_to_parent else None)
+                                            log_entry_type='pretix.plugins.sendmail.rule.order.position.email.sent')
+                            elif mail_to_parent and (parent_op.attendee_email != o.email or not o_sent):
+                                email_ctx = get_email_context(
+                                    event=e,
+                                    order=o,
+                                    invoice_address=ia,
+                                    position=parent_op,
+                                    event_or_subevent=self.subevent or e,
+                                )
+                                parent_op.send_mail(self.rule.subject, self.rule.template, email_ctx,
+                                                    attach_ical=self.rule.attach_ical,
+                                                    log_entry_type='pretix.plugins.sendmail.rule.order.position.email.sent')
                             elif not o_sent and o.email:
                                 email_ctx = get_email_context(
                                     event=e,