fix flake8

Co-authored-by: Richard Schreiber <wiffbi@gmail.com>

src/pretix/plugins/sendmail/forms.py

@@ -158,7 +158,12 @@ class OrderMailForm(BaseMailForm):
         ),
         label=pgettext_lazy('sendmail_form', 'Restrict to products'),
         required=True,
-        queryset=Item.objects.none()
+        queryset=Item.objects.none(),
+        help_text=pgettext_lazy(
+            'sendmail_form',
+            'There may be multiple mails sent out to the same mail address if one order contains multiple attendee '
+            'products for it, if you restrict to products while also restricting mails to attendees only. '
+            'This is intended, as every one of those get linked to their own separate order page restricted to only that product.')
     )
     filter_checkins = forms.BooleanField(
         label=_('Filter check-in status'),
@@ -371,6 +376,11 @@ class RuleForm(FormPlaceholderMixin, I18nModelForm):
             del self.fields['subevent']
 
         self.fields['limit_products'].queryset = Item.objects.filter(event=self.event)
+        self.fields['limit_products'].help_text = pgettext_lazy(
+            'sendmail_form',
+            'There may be multiple mails sent out to the same mail address if one order contains multiple attendee '
+            'products for it, if you restrict to products while also restricting mails to attendees only. '
+            'This is intended, as every one of those get linked to their own separate order page restricted to only that product.')
 
         self.fields['schedule_type'] = forms.ChoiceField(
             label=_('Type of schedule time'),

src/pretix/plugins/sendmail/models.py

@@ -19,6 +19,7 @@
 # You should have received a copy of the GNU Affero General Public License along with this program.  If not, see
 # <https://www.gnu.org/licenses/>.
 #
+import logging
 from datetime import datetime, time, timedelta
 
 from dateutil.tz import datetime_exists
@@ -39,6 +40,8 @@ from pretix.base.models import (
 )
 from pretix.base.models.base import LoggingMixin
 
+logger = logging.getLogger(__name__)
+
 
 class ScheduledMail(models.Model):
     STATE_SCHEDULED = 'scheduled'
@@ -167,14 +170,66 @@ class ScheduledMail(models.Model):
         for o in orders:
             with language(o.locale, e.settings.region):
                 positions = list(o.positions.all())
-                o_sent = False
+                send_to_order = send_to_orders
 
                 try:
                     ia = o.invoice_address
                 except InvoiceAddress.DoesNotExist:
                     ia = InvoiceAddress(order=o)
 
-                if send_to_orders and o.email:
+                if send_to_attendees:
+                    parent_op = None
+                    sent_to_positions = set()
+                    for p in positions:
+                        if p.addon_to_id is None:
+                            # this op might have matching add-ons, so save for later
+                            parent_op = p
+                        elif not parent_op or p.addon_to_id != parent_op.id:
+                            # this op is an add-on, but not to the current parent_op
+                            # something got mixed up as add-ons should always come directly after their parent
+                            logger.warning(f"Add-ons are mixed up for position #{p.positionid} in order {o.full_code}")
+                            continue
+
+                        if p.id not in position_ids:
+                            # not a matching op, just there for parent_op
+                            continue
+
+                        if not p.attendee_email and p.addon_to_id:
+                            # no email => try parent_op
+                            p = parent_op
+
+                        if not p.attendee_email:
+                            # still no email on => send to order
+                            send_to_order = True
+                            continue
+
+                        # attendee email available
+
+                        if p.addon_to_id and p.attendee_email == parent_op.attendee_email:
+                            # if op is add-on and parent's email match => send to parent
+                            p = parent_op
+
+                        if p.pk in sent_to_positions:
+                            # this position already got an email
+                            continue
+
+                        if p.attendee_email == o.email:
+                            send_to_order = True
+                            continue
+
+                        email_ctx = get_email_context(
+                            event=e,
+                            order=o,
+                            invoice_address=ia,
+                            position=p,
+                            event_or_subevent=self.subevent or e,
+                        )
+                        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')
+                        sent_to_positions.add(p.pk)
+
+                if send_to_order and o.email:
                     email_ctx = get_email_context(
                         event=e,
                         order=o,
@@ -184,38 +239,6 @@ class ScheduledMail(models.Model):
                     o.send_mail(self.rule.subject, self.rule.template, email_ctx,
                                 attach_ical=self.rule.attach_ical,
                                 log_entry_type='pretix.plugins.sendmail.rule.order.email.sent')
-                    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]
-
-                    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_ctx = get_email_context(
-                                    event=e,
-                                    order=o,
-                                    invoice_address=ia,
-                                    position=p,
-                                    event_or_subevent=self.subevent or e,
-                                )
-                                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')
-                            elif not o_sent and o.email:
-                                email_ctx = get_email_context(
-                                    event=e,
-                                    order=o,
-                                    invoice_address=ia,
-                                    event_or_subevent=self.subevent or e,
-                                )
-                                o.send_mail(self.rule.subject, self.rule.template, email_ctx,
-                                            attach_ical=self.rule.attach_ical,
-                                            log_entry_type='pretix.plugins.sendmail.rule.order.email.sent')
-                                o_sent = True
 
                 self.last_successful_order_id = o.pk
 

src/pretix/plugins/sendmail/tasks.py

@@ -31,6 +31,7 @@
 # Unless required by applicable law or agreed to in writing, software distributed under the Apache License 2.0 is
 # distributed on an "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied. See the
 # License for the specific language governing permissions and limitations under the License.
+import logging
 from datetime import datetime
 
 from django.db.models import Exists, OuterRef, Q
@@ -43,6 +44,8 @@ from pretix.base.services.mail import mail
 from pretix.base.services.tasks import ProfiledEventTask
 from pretix.celery_app import app
 
+logger = logging.getLogger(__name__)
+
 
 def _chunks(lst, n):
     """
@@ -70,6 +73,8 @@ def send_mails_to_orders(event: Event, user: int, subject: dict, message: dict,
         except InvoiceAddress.DoesNotExist:
             ia = InvoiceAddress(order=o)
 
+        parent_op = None
+        sent_to_positions = set()
         if recipients in ('both', 'attendees'):
             for p in o.positions.annotate(
                 any_checkins=Exists(
@@ -85,10 +90,16 @@ def send_mails_to_orders(event: Event, user: int, subject: dict, message: dict,
                     )
                 ),
             ).prefetch_related('addons', 'subevent'):
-                if p.addon_to_id is not None:
+
+                if p.addon_to_id is None:
+                    parent_op = p
+                elif not parent_op or p.addon_to_id != parent_op.id:
+                    # this op is an add-on, but not to the current parent_op
+                    # something got mixed up as add-ons should always come directly after their parent
+                    logger.warning(f"Add-ons are mixed up for position #{p.positionid} in order {o.full_code}")
                     continue
 
-                if p.item_id not in items and not any(a.item_id in items for a in p.addons.all()):
+                if p.item_id not in items:
                     continue
 
                 if filter_checkins:
@@ -99,13 +110,8 @@ def send_mails_to_orders(event: Event, user: int, subject: dict, message: dict,
                     if not allowed:
                         continue
 
-                if not p.attendee_email:
-                    if recipients == 'attendees':
-                        send_to_order = True
-                    continue
-
-                if p.attendee_email == o.email and send_to_order:
-                    continue
+                if not p.attendee_email and p.addon_to_id:
+                    p = parent_op
 
                 if subevent and p.subevent_id != subevent:
                     continue
@@ -116,6 +122,22 @@ def send_mails_to_orders(event: Event, user: int, subject: dict, message: dict,
                 if subevents_to and p.subevent.date_from >= subevents_to:
                     continue
 
+                if not p.attendee_email:
+                    send_to_order = True
+                    continue
+
+                if p.addon_to_id and p.attendee_email == parent_op.attendee_email:
+                    # if op is add-on and parent's email match => send to parent
+                    p = parent_op
+
+                if p.pk in sent_to_positions:
+                    # this position already got an email
+                    continue
+
+                if p.attendee_email == o.email:
+                    send_to_order = True
+                    continue
+
                 with language(o.locale, event.settings.region):
                     email_context = get_email_context(event=event, order=o, invoice_address=ia, position=p)
                     outgoing_mail = mail(
@@ -137,6 +159,7 @@ def send_mails_to_orders(event: Event, user: int, subject: dict, message: dict,
                             user=user,
                             data=outgoing_mail.log_data(),
                         )
+                    sent_to_positions.add(p.pk)
 
         if send_to_order and o.email:
             with language(o.locale, event.settings.region):

src/pretix/presale/views/order.py

@@ -174,7 +174,6 @@ class OrderPositionDetailMixin(NoSearchIndexViewMixin):
     def position(self):
         qs = OrderPosition.objects.filter(
             order__event=self.request.event,
-            addon_to__isnull=True,
             order__code=self.kwargs['order'],
             positionid=self.kwargs['position']
         ).select_related('order', 'order__event')

src/tests/plugins/sendmail/test_rules.py

@@ -197,6 +197,84 @@ def test_sendmail_rule_send_order_vs_pos(send_to, amount_mails, recipients, orde
     assert set(recipients) == set(_recipients)
 
 
+@pytest.mark.django_db
+@pytest.mark.parametrize('send_to,amount_mails,recipients,ticket_mail,addon_mail, products', [
+    (Rule.ATTENDEES, 1, ['addon-attendee@dummy.test'], 'attendee@dummy.test', 'addon-attendee@dummy.test', 'addon'),
+    (Rule.ATTENDEES, 2, ['attendee@dummy.test', 'addon-attendee@dummy.test'], 'attendee@dummy.test',
+     'addon-attendee@dummy.test', 'both'),
+    (Rule.ATTENDEES, 1, ['attendee@dummy.test'], 'attendee@dummy.test', 'attendee@dummy.test', 'both'),
+    (Rule.ATTENDEES, 1, ['attendee@dummy.test'], 'attendee@dummy.test', None, 'addon'),
+    (Rule.ATTENDEES, 1, ['attendee@dummy.test'], 'attendee@dummy.test', None, 'both'),
+    (Rule.ATTENDEES, 1, ['dummy@dummy.test'], None, None, 'addon'),
+    (Rule.ATTENDEES, 1, ['dummy@dummy.test'], None, None, 'both'),
+    (Rule.ATTENDEES, 2, ['dummy@dummy.test', 'addon-attendee@dummy.test'], None, 'addon-attendee@dummy.test', 'both'),
+    (Rule.ATTENDEES, 1, ['dummy@dummy.test'], None, None, 'all'),
+    (Rule.ATTENDEES, 2, ['dummy@dummy.test', 'addon-attendee@dummy.test'], None, 'addon-attendee@dummy.test', 'all'),
+])
+@scopes_disabled()
+def test_sendmail_rule_send_addons(send_to, amount_mails, recipients, ticket_mail, addon_mail, products, order,
+                                   event, pos, item, item2):
+    djmail.outbox = []
+
+    order.status = order.STATUS_PAID
+    order.save()
+
+    p = pos
+    p.attendee_email = ticket_mail
+    p.save()
+    order.all_positions.create(item=item2, price=0, attendee_email=addon_mail, addon_to=p)
+    rule = order.event.sendmail_rules.create(date_is_absolute=True, send_date=dt_now - datetime.timedelta(hours=1),
+                                             send_to=send_to, subject='meow', template='meow meow meow',
+                                             all_products=products == 'all')
+    if products == 'addon':
+        rule.limit_products.set([item2])
+    if products == 'both':
+        rule.limit_products.set([item, item2])
+
+    sendmail_run_rules(None)
+
+    assert len(djmail.outbox) == amount_mails
+
+    _recipients = [mail.to[0] for mail in djmail.outbox]
+    assert set(recipients) == set(_recipients)
+
+
+@pytest.mark.django_db
+@pytest.mark.parametrize('send_to,amount_mails,recipients,ticket_mail,addon_mail, products', [
+    (Rule.ATTENDEES, 2, ['attendee@dummy.test', 'addon-attendee@dummy.test'], 'attendee@dummy.test',
+     'addon-attendee@dummy.test', 'addon'),
+    (Rule.ATTENDEES, 2, ['attendee@dummy.test', 'addon-attendee@dummy.test'], 'attendee@dummy.test',
+     'addon-attendee@dummy.test', 'both'),
+])
+@scopes_disabled()
+def test_sendmail_rule_send_addons_one_unp(send_to, amount_mails, recipients, ticket_mail, addon_mail, products, order,
+                                           event, pos, item, item2):
+    djmail.outbox = []
+
+    order.status = order.STATUS_PAID
+    order.save()
+
+    p = pos
+    p.attendee_email = ticket_mail
+    p.save()
+    order.all_positions.create(item=item2, price=0, attendee_email=addon_mail, addon_to=p)
+    order.all_positions.create(item=item2, price=0, addon_to=p)
+    rule = order.event.sendmail_rules.create(date_is_absolute=True, send_date=dt_now - datetime.timedelta(hours=1),
+                                             send_to=send_to, subject='meow', template='meow meow meow',
+                                             all_products=False)
+    if products == 'addon':
+        rule.limit_products.set([item2])
+    if products == 'both':
+        rule.limit_products.set([item, item2])
+
+    sendmail_run_rules(None)
+
+    assert len(djmail.outbox) == amount_mails
+
+    _recipients = [mail.to[0] for mail in djmail.outbox]
+    assert set(recipients) == set(_recipients)
+
+
 @pytest.mark.django_db
 @scopes_disabled()
 def test_sendmail_rule_send_attendees_unset_mail(order, event, item):

src/tests/plugins/sendmail/test_sendmail.py

@@ -406,6 +406,312 @@ def test_sendmail_attendee_product_filter(logged_in_client, sendmail_url, event,
     assert '/order/' not in djmail.outbox[0].body
 
 
+@pytest.mark.django_db
+def test_sendmail_attendee_addon_filter(logged_in_client, sendmail_url, event, order, pos):
+    event.settings.attendee_emails_asked = True
+    with scopes_disabled():
+        addon = Item.objects.create(name='Test addon', event=event, default_price=12)
+        p = pos
+        p.attendee_email = 'attendee1@dummy.test'
+        p.save()
+        order.positions.create(
+            item=addon, price=0, attendee_email='add-on-attendee@dummy.test', addon_to=p
+        )
+
+        djmail.outbox = []
+        response = logged_in_client.post(sendmail_url + 'orders/',
+                                         {'sendto': 'na',
+                                          'action': 'send',
+                                          'recipients': 'attendees',
+                                          'items': addon.pk,
+                                          'subject_0': 'Test subject',
+                                          'message_0': 'This is a test file for sending mails.',
+                                          },
+                                         follow=True)
+    assert response.status_code == 200
+    assert 'alert-success' in response.rendered_content
+    assert len(djmail.outbox) == 1
+    assert djmail.outbox[0].to == ['add-on-attendee@dummy.test']
+    assert '/ticket/' in djmail.outbox[0].body
+    assert '/order/' not in djmail.outbox[0].body
+
+
+@pytest.mark.django_db
+def test_sendmail_attendee_ticket_and_addon_filter(logged_in_client, sendmail_url, event, order, pos):
+    event.settings.attendee_emails_asked = True
+    with scopes_disabled():
+        addon = Item.objects.create(name='Test addon', event=event, default_price=12)
+        p = pos
+        p.attendee_email = 'attendee1@dummy.test'
+        p.save()
+        order.positions.create(
+            item=addon, price=0, attendee_email='add-on-attendee@dummy.test', addon_to=p
+        )
+
+        djmail.outbox = []
+        response = logged_in_client.post(sendmail_url + 'orders/',
+                                         {'sendto': 'na',
+                                          'action': 'send',
+                                          'recipients': 'attendees',
+                                          'items': {addon.pk, p.item_id},
+                                          'subject_0': 'Test subject',
+                                          'message_0': 'This is a test file for sending mails.',
+                                          },
+                                         follow=True)
+    assert response.status_code == 200
+    assert 'alert-success' in response.rendered_content
+    assert len(djmail.outbox) == 2
+    for msg in djmail.outbox:
+        assert msg.to in [['attendee1@dummy.test'], ['add-on-attendee@dummy.test']]
+        assert '/ticket/' in msg.body
+        assert '/order/' not in msg.body
+
+
+@pytest.mark.django_db
+def test_sendmail_attendee_ticket_and_same_addon_filter(logged_in_client, sendmail_url, event, order, pos):
+    event.settings.attendee_emails_asked = True
+    with scopes_disabled():
+        addon = Item.objects.create(name='Test addon', event=event, default_price=12)
+        p = pos
+        p.attendee_email = 'attendee1@dummy.test'
+        p.save()
+        order.positions.create(
+            item=addon, price=0, attendee_email='attendee1@dummy.test', addon_to=p
+        )
+
+        djmail.outbox = []
+        response = logged_in_client.post(sendmail_url + 'orders/',
+                                         {'sendto': 'na',
+                                          'action': 'send',
+                                          'recipients': 'attendees',
+                                          'items': {addon.pk, p.item_id},
+                                          'subject_0': 'Test subject',
+                                          'message_0': 'This is a test file for sending mails.',
+                                          },
+                                         follow=True)
+    assert response.status_code == 200
+    assert 'alert-success' in response.rendered_content
+    assert len(djmail.outbox) == 1
+    assert djmail.outbox[0].to == ['attendee1@dummy.test']
+    assert '/ticket/' in djmail.outbox[0].body
+    assert '/order/' not in djmail.outbox[0].body
+
+
+@pytest.mark.django_db
+def test_sendmail_attendee_addon_unpersonalized_filter(logged_in_client, sendmail_url, event, order, pos):
+    event.settings.attendee_emails_asked = True
+    with scopes_disabled():
+        addon = Item.objects.create(name='Test addon', event=event, default_price=12)
+        p = pos
+        p.attendee_email = 'attendee1@dummy.test'
+        p.save()
+        order.positions.create(
+            item=addon, price=0, addon_to=p
+        )
+
+        djmail.outbox = []
+        response = logged_in_client.post(sendmail_url + 'orders/',
+                                         {'sendto': 'na',
+                                          'action': 'send',
+                                          'recipients': 'attendees',
+                                          'items': addon.pk,
+                                          'subject_0': 'Test subject',
+                                          'message_0': 'This is a test file for sending mails.',
+                                          },
+                                         follow=True)
+    assert response.status_code == 200
+    assert 'alert-success' in response.rendered_content
+    assert len(djmail.outbox) == 1
+    assert djmail.outbox[0].to == ['attendee1@dummy.test']
+    assert '/ticket/' in djmail.outbox[0].body
+    assert '/order/' not in djmail.outbox[0].body
+
+
+@pytest.mark.django_db
+def test_sendmail_attendee_ticket_and_addon_unp_filter(logged_in_client, sendmail_url, event, order, pos):
+    event.settings.attendee_emails_asked = True
+    with scopes_disabled():
+        addon = Item.objects.create(name='Test addon', event=event, default_price=12)
+        p = pos
+        p.attendee_email = 'attendee1@dummy.test'
+        p.save()
+        order.positions.create(
+            item=addon, price=0, addon_to=p
+        )
+
+        djmail.outbox = []
+        response = logged_in_client.post(sendmail_url + 'orders/',
+                                         {'sendto': 'na',
+                                          'action': 'send',
+                                          'recipients': 'attendees',
+                                          'items': {addon.pk, p.item_id},
+                                          'subject_0': 'Test subject',
+                                          'message_0': 'This is a test file for sending mails.',
+                                          },
+                                         follow=True)
+    assert response.status_code == 200
+    assert 'alert-success' in response.rendered_content
+    assert len(djmail.outbox) == 1
+    assert djmail.outbox[0].to == ['attendee1@dummy.test']
+    assert '/ticket/' in djmail.outbox[0].body
+    assert '/order/' not in djmail.outbox[0].body
+
+
+@pytest.mark.django_db
+def test_sendmail_attendee_ticket_unp_and_addon_filter(logged_in_client, sendmail_url, event, order, pos):
+    event.settings.attendee_emails_asked = True
+    with scopes_disabled():
+        addon = Item.objects.create(name='Test addon', event=event, default_price=12)
+        order.positions.create(
+            item=addon, price=0, attendee_email='add-on-attendee@dummy.test', addon_to=pos
+        )
+
+        djmail.outbox = []
+        response = logged_in_client.post(sendmail_url + 'orders/',
+                                         {'sendto': 'na',
+                                          'action': 'send',
+                                          'recipients': 'attendees',
+                                          'items': {addon.pk, pos.item_id},
+                                          'subject_0': 'Test subject',
+                                          'message_0': 'This is a test file for sending mails.',
+                                          },
+                                         follow=True)
+    assert response.status_code == 200
+    assert 'alert-success' in response.rendered_content
+    assert len(djmail.outbox) == 2
+    for msg in djmail.outbox:
+        assert msg.to in [[order.email], ['add-on-attendee@dummy.test']]
+        if msg.to == [order.email]:
+            assert '/ticket/' not in msg.body
+            assert '/order/' in msg.body
+        else:
+            assert msg.to == ['add-on-attendee@dummy.test']
+            assert '/ticket/' in msg.body
+            assert '/order/' not in msg.body
+
+
+@pytest.mark.django_db
+def test_sendmail_attendee_addon_unp_unp_filter(logged_in_client, sendmail_url, event, order, pos):
+    event.settings.attendee_emails_asked = True
+    with scopes_disabled():
+        addon = Item.objects.create(name='Test addon', event=event, default_price=12)
+        order.positions.create(
+            item=addon, price=0, addon_to=pos
+        )
+
+        djmail.outbox = []
+        response = logged_in_client.post(sendmail_url + 'orders/',
+                                         {'sendto': 'na',
+                                          'action': 'send',
+                                          'recipients': 'attendees',
+                                          'items': addon.pk,
+                                          'subject_0': 'Test subject',
+                                          'message_0': 'This is a test file for sending mails.',
+                                          },
+                                         follow=True)
+    assert response.status_code == 200
+    assert 'alert-success' in response.rendered_content
+    assert len(djmail.outbox) == 1
+    assert djmail.outbox[0].to == [order.email]
+    assert '/ticket/' not in djmail.outbox[0].body
+    assert '/order/' in djmail.outbox[0].body
+
+
+@pytest.mark.django_db
+def test_sendmail_attendee_and_addon_unp_unp_filter(logged_in_client, sendmail_url, event, order, pos):
+    event.settings.attendee_emails_asked = True
+    with scopes_disabled():
+        addon = Item.objects.create(name='Test addon', event=event, default_price=12)
+        order.positions.create(
+            item=addon, price=0, addon_to=pos
+        )
+
+        djmail.outbox = []
+        response = logged_in_client.post(sendmail_url + 'orders/',
+                                         {'sendto': 'na',
+                                          'action': 'send',
+                                          'recipients': 'attendees',
+                                          'items': {addon.pk, pos.item_id},
+                                          'subject_0': 'Test subject',
+                                          'message_0': 'This is a test file for sending mails.',
+                                          },
+                                         follow=True)
+    assert response.status_code == 200
+    assert 'alert-success' in response.rendered_content
+    assert len(djmail.outbox) == 1
+    assert djmail.outbox[0].to == [order.email]
+    assert '/ticket/' not in djmail.outbox[0].body
+    assert '/order/' in djmail.outbox[0].body
+
+
+@pytest.mark.django_db
+def test_sendmail_attendee_two_addons_one_unp_filter(logged_in_client, sendmail_url, event, order, pos):
+    event.settings.attendee_emails_asked = True
+    with scopes_disabled():
+        p = pos
+        p.attendee_email = 'attendee1@dummy.test'
+        p.save()
+        addon = Item.objects.create(name='Test addon', event=event, default_price=12)
+        order.positions.create(
+            item=addon, price=0, attendee_email='add-on-attendee@dummy.test', addon_to=p
+        )
+        order.positions.create(
+            item=addon, price=0, addon_to=p
+        )
+
+        djmail.outbox = []
+        response = logged_in_client.post(sendmail_url + 'orders/',
+                                         {'sendto': 'na',
+                                          'action': 'send',
+                                          'recipients': 'attendees',
+                                          'items': addon.pk,
+                                          'subject_0': 'Test subject',
+                                          'message_0': 'This is a test file for sending mails.',
+                                          },
+                                         follow=True)
+    assert response.status_code == 200
+    assert 'alert-success' in response.rendered_content
+    assert len(djmail.outbox) == 2
+    for msg in djmail.outbox:
+        assert msg.to in [['attendee1@dummy.test'], ['add-on-attendee@dummy.test']]
+        assert '/ticket/' in msg.body
+        assert '/order/' not in msg.body
+
+
+@pytest.mark.django_db
+def test_sendmail_attendee_and_two_addons_one_unp_filter(logged_in_client, sendmail_url, event, order, pos):
+    event.settings.attendee_emails_asked = True
+    with scopes_disabled():
+        p = pos
+        p.attendee_email = 'attendee1@dummy.test'
+        p.save()
+        addon = Item.objects.create(name='Test addon', event=event, default_price=12)
+        order.positions.create(
+            item=addon, price=0, attendee_email='add-on-attendee@dummy.test', addon_to=p
+        )
+        order.positions.create(
+            item=addon, price=0, addon_to=p
+        )
+
+        djmail.outbox = []
+        response = logged_in_client.post(sendmail_url + 'orders/',
+                                         {'sendto': 'na',
+                                          'action': 'send',
+                                          'recipients': 'attendees',
+                                          'items': {addon.pk, p.item_id},
+                                          'subject_0': 'Test subject',
+                                          'message_0': 'This is a test file for sending mails.',
+                                          },
+                                         follow=True)
+    assert response.status_code == 200
+    assert 'alert-success' in response.rendered_content
+    assert len(djmail.outbox) == 2
+    for msg in djmail.outbox:
+        assert msg.to in [['attendee1@dummy.test'], ['add-on-attendee@dummy.test']]
+        assert '/ticket/' in msg.body
+        assert '/order/' not in msg.body
+
+
 @pytest.mark.django_db
 def test_sendmail_attendee_subevent_filter(logged_in_client, sendmail_url, event, item, order, pos):
     event.settings.attendee_emails_asked = True