diff --git a/src/pretix/base/models/orders.py b/src/pretix/base/models/orders.py
index 01844c82f8..ceea5dd10c 100644
--- a/src/pretix/base/models/orders.py
+++ b/src/pretix/base/models/orders.py
@@ -2912,7 +2912,8 @@ class OrderPosition(AbstractPosition):
     def send_mail(self, subject: str, template: Union[str, LazyI18nString],
                   context: Dict[str, Any]=None, log_entry_type: str='pretix.event.order.email.sent',
                   user: User=None, headers: dict=None, sender: str=None, invoices: list=None,
-                  auth=None, attach_tickets=False, attach_ical=False, attach_other_files: list=None):
+                  auth=None, attach_tickets=False, attach_ical=False, attach_other_files: list = None,
+                  diff_recipient=None):
         """
         Sends an email to the attendee. Basically, this method does two things:
 
@@ -2930,14 +2931,15 @@ class OrderPosition(AbstractPosition):
         :param sender: Custom email sender.
         :param attach_tickets: Attach tickets of this order, if they are existing and ready to download
         :param attach_ical: Attach relevant ICS files
+        :param diff_recipient: A different recipient in case of unpersonalized add-ons.
         """
         from pretix.base.services.mail import mail
 
-        if not self.attendee_email:
+        if not self.attendee_email and not self.diff_recipient:
             return
 
         with language(self.order.locale, self.order.event.settings.region):
-            recipient = self.attendee_email
+            recipient = self.attendee_email if self.attendee_email else self.diff_recipient
             outgoing_mail = mail(
                 recipient, subject, template, context,
                 self.event, self.order.locale, order=self.order, headers=headers, sender=sender,
diff --git a/src/pretix/plugins/sendmail/models.py b/src/pretix/plugins/sendmail/models.py
index b68916c010..c98a19e1d2 100644
--- a/src/pretix/plugins/sendmail/models.py
+++ b/src/pretix/plugins/sendmail/models.py
@@ -194,7 +194,19 @@ class ScheduledMail(models.Model):
 
                     for p in positions:
                         if p.id in position_ids:
-                            if p.attendee_email and (p.attendee_email != o.email or not o_sent):
+                            email_to = p.attendee_email if p.attendee_email else None
+
+                            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
+
+                            if email_to != o.email or not o_sent:
                                 email_ctx = get_email_context(
                                     event=e,
                                     order=o,
@@ -204,7 +216,8 @@ 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')
+                                            log_entry_type='pretix.plugins.sendmail.rule.order.position.email.sent',
+                                            diff_recipient=email_to if mail_to_parent else None)
                             elif not o_sent and o.email:
                                 email_ctx = get_email_context(
                                     event=e,
@@ -227,7 +240,8 @@ class Rule(models.Model, LoggingMixin):
 
     SEND_TO_CHOICES = [
         (CUSTOMERS, _("Everyone who created a ticket order")),
-        (ATTENDEES, _("Every attendee (falling back to the order contact when no attendee email address is given)")),
+        (ATTENDEES,
+         _("Every attendee (falling back to the order contact when no attendee email address is given or the ticket's contact in the case of add-ons)")),
         (BOTH, _('Both (all order contact addresses and all attendee email addresses)'))
     ]