Model-based mail queuing

src/pretix/api/serializers/organizer.py

@@ -49,7 +49,7 @@ from pretix.base.plugins import (
     PLUGIN_LEVEL_EVENT, PLUGIN_LEVEL_EVENT_ORGANIZER_HYBRID,
     PLUGIN_LEVEL_ORGANIZER,
 )
-from pretix.base.services.mail import SendMailException, mail
+from pretix.base.services.mail import mail
 from pretix.base.settings import validate_organizer_settings
 from pretix.helpers.urls import build_absolute_uri as build_global_uri
 from pretix.multidomain.urlreverse import build_absolute_uri
@@ -363,24 +363,21 @@ class TeamInviteSerializer(serializers.ModelSerializer):
         )
 
     def _send_invite(self, instance):
-        try:
-            mail(
-                instance.email,
-                _('pretix account invitation'),
-                'pretixcontrol/email/invitation.txt',
-                {
-                    'user': self,
-                    'organizer': self.context['organizer'].name,
-                    'team': instance.team.name,
-                    'url': build_global_uri('control:auth.invite', kwargs={
-                        'token': instance.token
-                    })
-                },
-                event=None,
-                locale=get_language_without_region()  # TODO: expose?
-            )
-        except SendMailException:
-            pass  # Already logged
+        mail(
+            instance.email,
+            _('pretix account invitation'),
+            'pretixcontrol/email/invitation.txt',
+            {
+                'user': self,
+                'organizer': self.context['organizer'].name,
+                'team': instance.team.name,
+                'url': build_global_uri('control:auth.invite', kwargs={
+                    'token': instance.token
+                })
+            },
+            event=None,
+            locale=get_language_without_region()  # TODO: expose?
+        )
 
     def create(self, validated_data):
         if 'email' in validated_data:

src/pretix/api/views/order.py

@@ -90,7 +90,6 @@ from pretix.base.services.invoices import (
     generate_cancellation, generate_invoice, invoice_pdf, invoice_qualified,
     regenerate_invoice, transmit_invoice,
 )
-from pretix.base.services.mail import SendMailException
 from pretix.base.services.orders import (
     OrderChangeManager, OrderError, _order_placed_email,
     _order_placed_email_attendee, approve_order, cancel_order, deny_order,
@@ -438,8 +437,6 @@ class EventOrderViewSet(OrderViewSetMixin, viewsets.ModelViewSet):
                 return Response({'detail': str(e)}, status=status.HTTP_400_BAD_REQUEST)
             except PaymentException as e:
                 return Response({'detail': str(e)}, status=status.HTTP_400_BAD_REQUEST)
-            except SendMailException:
-                pass
 
             return self.retrieve(request, [], **kwargs)
         return Response(
@@ -633,10 +630,7 @@ class EventOrderViewSet(OrderViewSetMixin, viewsets.ModelViewSet):
         order = self.get_object()
         if not order.email:
             return Response({'detail': 'There is no email address associated with this order.'}, status=status.HTTP_400_BAD_REQUEST)
-        try:
-            order.resend_link(user=self.request.user, auth=self.request.auth)
-        except SendMailException:
-            return Response({'detail': _('There was an error sending the mail. Please try again later.')}, status=status.HTTP_503_SERVICE_UNAVAILABLE)
+        order.resend_link(user=self.request.user, auth=self.request.auth)
 
         return Response(
             status=status.HTTP_204_NO_CONTENT
@@ -1609,8 +1603,6 @@ class PaymentViewSet(CreateModelMixin, viewsets.ReadOnlyModelViewSet):
                     )
                 except Quota.QuotaExceededException:
                     pass
-                except SendMailException:
-                    pass
 
             serializer = OrderPaymentSerializer(r, context=serializer.context)
 
@@ -1648,8 +1640,6 @@ class PaymentViewSet(CreateModelMixin, viewsets.ReadOnlyModelViewSet):
             return Response({'detail': str(e)}, status=status.HTTP_400_BAD_REQUEST)
         except PaymentException as e:
             return Response({'detail': str(e)}, status=status.HTTP_400_BAD_REQUEST)
-        except SendMailException:
-            pass
         return self.retrieve(request, [], **kwargs)
 
     @action(detail=True, methods=['POST'])

src/pretix/base/invoicing/email.py

@@ -33,7 +33,7 @@ from pretix.base.invoicing.transmission import (
     transmission_types,
 )
 from pretix.base.models import Invoice, InvoiceAddress
-from pretix.base.services.mail import SendMailException, mail, render_mail
+from pretix.base.services.mail import mail, render_mail
 from pretix.helpers.format import format_map
 
 
@@ -133,41 +133,37 @@ class EmailTransmissionProvider(TransmissionProvider):
             template = invoice.order.event.settings.get('mail_text_order_invoice', as_type=LazyI18nString)
             subject = invoice.order.event.settings.get('mail_subject_order_invoice', as_type=LazyI18nString)
 
-            try:
-                # Do not set to completed because that is done by the email sending task
-                subject = format_map(subject, context)
-                email_content = render_mail(template, context)
-                mail(
-                    [recipient],
-                    subject,
-                    template,
-                    context=context,
-                    event=invoice.order.event,
-                    locale=invoice.order.locale,
-                    order=invoice.order,
-                    invoices=[invoice],
-                    attach_tickets=False,
-                    auto_email=True,
-                    attach_ical=False,
-                    plain_text_only=True,
-                    no_order_links=True,
-                )
-            except SendMailException:
-                raise
-            else:
-                invoice.order.log_action(
-                    'pretix.event.order.email.invoice',
-                    user=None,
-                    auth=None,
-                    data={
-                        'subject': subject,
-                        'message': email_content,
-                        'position': None,
-                        'recipient': recipient,
-                        'invoices': [invoice.pk],
-                        'attach_tickets': False,
-                        'attach_ical': False,
-                        'attach_other_files': [],
-                        'attach_cached_files': [],
-                    }
-                )
+            # Do not set to completed because that is done by the email sending task
+            subject = format_map(subject, context)
+            email_content = render_mail(template, context)
+            mail(
+                [recipient],
+                subject,
+                template,
+                context=context,
+                event=invoice.order.event,
+                locale=invoice.order.locale,
+                order=invoice.order,
+                invoices=[invoice],
+                attach_tickets=False,
+                auto_email=True,
+                attach_ical=False,
+                plain_text_only=True,
+                no_order_links=True,
+            )
+            invoice.order.log_action(
+                'pretix.event.order.email.invoice',
+                user=None,
+                auth=None,
+                data={
+                    'subject': subject,
+                    'message': email_content,
+                    'position': None,
+                    'recipient': recipient,
+                    'invoices': [invoice.pk],
+                    'attach_tickets': False,
+                    'attach_ical': False,
+                    'attach_other_files': [],
+                    'attach_cached_files': [],
+                }
+            )

src/pretix/base/migrations/0289_outgoingmail.py

@@ -0,0 +1,112 @@
+# Generated by Django 4.2.17 on 2025-09-04 12:35
+
+import django.db.models.deletion
+from django.conf import settings
+from django.db import migrations, models
+
+
+class Migration(migrations.Migration):
+
+    dependencies = [
+        ("pretixbase", "0288_invoice_transmission"),
+    ]
+
+    operations = [
+        migrations.CreateModel(
+            name="OutgoingMail",
+            fields=[
+                (
+                    "id",
+                    models.BigAutoField(
+                        auto_created=True, primary_key=True, serialize=False
+                    ),
+                ),
+                ("status", models.CharField(default="queued", max_length=200)),
+                ("created", models.DateTimeField(auto_now_add=True)),
+                ("sent", models.DateTimeField(blank=True, null=True)),
+                ("error", models.TextField(null=True)),
+                ("error_detail", models.TextField(null=True)),
+                ("subject", models.TextField()),
+                ("body_plain", models.TextField()),
+                ("body_html", models.TextField()),
+                ("sender", models.CharField(max_length=500)),
+                ("headers", models.JSONField(default=dict)),
+                ("to", models.JSONField(default=list)),
+                ("cc", models.JSONField(default=list)),
+                ("bcc", models.JSONField(default=list)),
+                ("should_attach_tickets", models.BooleanField(default=False)),
+                ("should_attach_ical", models.BooleanField(default=False)),
+                ("should_attach_other_files", models.JSONField(default=list)),
+                ("actual_attachments", models.JSONField(default=list)),
+                (
+                    "customer",
+                    models.ForeignKey(
+                        null=True,
+                        on_delete=django.db.models.deletion.SET_NULL,
+                        related_name="outgoing_mails",
+                        to="pretixbase.customer",
+                    ),
+                ),
+                (
+                    "event",
+                    models.ForeignKey(
+                        null=True,
+                        on_delete=django.db.models.deletion.SET_NULL,
+                        related_name="outgoing_mails",
+                        to="pretixbase.event",
+                    ),
+                ),
+                (
+                    "order",
+                    models.ForeignKey(
+                        null=True,
+                        on_delete=django.db.models.deletion.SET_NULL,
+                        related_name="outgoing_mails",
+                        to="pretixbase.order",
+                    ),
+                ),
+                (
+                    "orderposition",
+                    models.ForeignKey(
+                        null=True,
+                        on_delete=django.db.models.deletion.SET_NULL,
+                        related_name="outgoing_mails",
+                        to="pretixbase.orderposition",
+                    ),
+                ),
+                (
+                    "organizer",
+                    models.ForeignKey(
+                        null=True,
+                        on_delete=django.db.models.deletion.CASCADE,
+                        related_name="outgoing_mails",
+                        to="pretixbase.organizer",
+                    ),
+                ),
+                (
+                    "should_attach_cached_files",
+                    models.ManyToManyField(
+                        related_name="outgoing_mails", to="pretixbase.cachedfile"
+                    ),
+                ),
+                (
+                    "should_attach_invoices",
+                    models.ManyToManyField(
+                        related_name="outgoing_mails", to="pretixbase.invoice"
+                    ),
+                ),
+                (
+                    "user",
+                    models.ForeignKey(
+                        null=True,
+                        on_delete=django.db.models.deletion.SET_NULL,
+                        related_name="outgoing_mails",
+                        to=settings.AUTH_USER_MODEL,
+                    ),
+                ),
+            ],
+            options={
+                "ordering": ("-created",),
+            },
+        ),
+    ]

src/pretix/base/models/__init__.py

@@ -40,6 +40,7 @@ from .items import (
     SubEventItem, SubEventItemVariation, itempicture_upload_to,
 )
 from .log import LogEntry
+from .mail import OutgoingMail
 from .media import ReusableMedium
 from .memberships import Membership, MembershipType
 from .notifications import NotificationSetting

src/pretix/base/models/auth.py

@@ -331,27 +331,24 @@ class User(AbstractBaseUser, PermissionsMixin, LoggingMixin):
             return self.email
 
     def send_security_notice(self, messages, email=None):
-        from pretix.base.services.mail import SendMailException, mail
+        from pretix.base.services.mail import mail
 
-        try:
-            with language(self.locale):
-                msg = '- ' + '\n- '.join(str(m) for m in messages)
+        with language(self.locale):
+            msg = '- ' + '\n- '.join(str(m) for m in messages)
 
-            mail(
-                email or self.email,
-                _('Account information changed'),
-                'pretixcontrol/email/security_notice.txt',
-                {
-                    'user': self,
-                    'messages': msg,
-                    'url': build_absolute_uri('control:user.settings')
-                },
-                event=None,
-                user=self,
-                locale=self.locale
-            )
-        except SendMailException:
-            pass  # Already logged
+        mail(
+            email or self.email,
+            _('Account information changed'),
+            'pretixcontrol/email/security_notice.txt',
+            {
+                'user': self,
+                'messages': msg,
+                'url': build_absolute_uri('control:user.settings')
+            },
+            event=None,
+            user=self,
+            locale=self.locale
+        )
 
     def send_password_reset(self):
         from pretix.base.services.mail import mail

src/pretix/base/models/mail.py

@@ -0,0 +1,149 @@
+#
+# This file is part of pretix (Community Edition).
+#
+# Copyright (C) 2014-2020 Raphael Michel and contributors
+# Copyright (C) 2020-2021 rami.io GmbH and contributors
+#
+# This program is free software: you can redistribute it and/or modify it under the terms of the GNU Affero General
+# Public License as published by the Free Software Foundation in version 3 of the License.
+#
+# ADDITIONAL TERMS APPLY: Pursuant to Section 7 of the GNU Affero General Public License, additional terms are
+# applicable granting you additional permissions and placing additional restrictions on your usage of this software.
+# Please refer to the pretix LICENSE file to obtain the full terms applicable to this work. If you did not receive
+# this file, see <https://pretix.eu/about/en/license>.
+#
+# This program is distributed in the hope that it will be useful, but WITHOUT ANY WARRANTY; without even the implied
+# warranty of MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the GNU Affero General Public License for more
+# details.
+#
+# 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/>.
+#
+from django.core.mail import get_connection
+from django.db import models
+from django.utils.translation import gettext_lazy as _
+from django_scopes import scope, scopes_disabled
+
+
+class OutgoingMail(models.Model):
+    STATUS_QUEUED = "queued"
+    STATUS_INFLIGHT = "inflight"
+    STATUS_AWAWITING_RETRY = "awaiting_retry"
+    STATUS_FAILED = "failed"
+    STATUS_SENT = "sent"
+    STATUS_CHOICES = (
+        (STATUS_QUEUED, _("queued")),
+        (STATUS_INFLIGHT, _("being sent")),
+        (STATUS_AWAWITING_RETRY, _("awaiting retry")),
+        (STATUS_FAILED, _("failed")),
+        (STATUS_SENT, _("sent")),
+    )
+
+    status = models.CharField(max_length=200, choices=STATUS_CHOICES, default=STATUS_QUEUED)
+    created = models.DateTimeField(auto_now_add=True)
+    sent = models.DateTimeField(null=True, blank=True)
+    error = models.TextField(null=True, blank=True)
+    error_detail = models.TextField(null=True, blank=True)
+
+    organizer = models.ForeignKey(
+        'pretixbase.Organizer',
+        on_delete=models.CASCADE,
+        related_name='outgoing_mails',
+        null=True, blank=True,
+    )
+    event = models.ForeignKey(
+        'pretixbase.Event',
+        on_delete=models.SET_NULL,  # todo think, only for non-queued!
+        related_name='outgoing_mails',
+        null=True, blank=True,
+    )
+    order = models.ForeignKey(
+        'pretixbase.Order',
+        on_delete=models.SET_NULL,
+        related_name='outgoing_mails',
+        null=True, blank=True,
+    )
+    orderposition = models.ForeignKey(
+        'pretixbase.OrderPosition',
+        on_delete=models.SET_NULL,
+        related_name='outgoing_mails',
+        null=True, blank=True,
+    )
+    customer = models.ForeignKey(
+        'pretixbase.Customer',
+        on_delete=models.SET_NULL,
+        related_name='outgoing_mails',
+        null=True, blank=True,
+    )
+    user = models.ForeignKey(
+        'pretixbase.User',
+        on_delete=models.SET_NULL,
+        related_name='outgoing_mails',
+        null=True, blank=True,
+    )
+
+    subject = models.TextField()
+    body_plain = models.TextField()
+    body_html = models.TextField()
+    sender = models.CharField(max_length=500)
+    headers = models.JSONField(default=dict)
+    to = models.JSONField(default=list)
+    cc = models.JSONField(default=list)
+    bcc = models.JSONField(default=list)
+
+    should_attach_invoices = models.ManyToManyField(
+        'pretixbase.Invoice',
+        related_name='outgoing_mails'
+    )
+    should_attach_tickets = models.BooleanField(default=False)
+    should_attach_ical = models.BooleanField(default=False)
+    should_attach_cached_files = models.ManyToManyField(
+        'pretixbase.CachedFile',
+        related_name='outgoing_mails',
+    )
+    should_attach_other_files = models.JSONField(default=list)
+
+    actual_attachments = models.JSONField(default=list)
+
+    class Meta:
+        ordering = ('-created',)
+
+    def get_mail_backend(self):
+        if self.event:
+            return self.event.get_mail_backend()
+        elif self.organizer:
+            return self.organizer.get_mail_backend()
+        else:
+            return get_connection(fail_silently=False)
+
+    def scope_manager(self):
+        if self.organizer:
+            return scope(organizer=self.organizer)  # noqa
+        else:
+            return scopes_disabled()  # noqa
+
+    def save(self, *args, **kwargs):
+        if self.orderposition_id and not self.order_id:
+            self.order = self.orderposition.order
+        if self.order_id and not self.event_id:
+            self.event = self.order.event
+        if self.event_id and not self.organizer_id:
+            self.organizer = self.event.organizer
+        if self.customer_id and not self.organizer_id:
+            self.organizer = self.customer.organizer
+        super().save(*args, **kwargs)
+
+    def log_parameters(self):
+        if self.order:
+            error_log_action_type = 'pretix.event.order.email.error'
+            log_target = self.order
+        elif self.customer:
+            error_log_action_type = 'pretix.customer.email.error'
+            log_target = self.customer
+        elif self.user:
+            error_log_action_type = 'pretix.user.email.error'
+            log_target = self.user
+        else:
+            error_log_action_type = 'pretix.email.error'
+            log_target = None
+        return log_target, error_log_action_type

src/pretix/base/models/orders.py

@@ -1162,9 +1162,7 @@ class Order(LockModel, LoggedModel):
                          only be attached for this position and child positions, the link will only point to the
                          position and the attendee email will be used if available.
         """
-        from pretix.base.services.mail import (
-            SendMailException, mail, render_mail,
-        )
+        from pretix.base.services.mail import mail, render_mail
 
         if not self.email and not (position and position.attendee_email):
             return
@@ -1174,35 +1172,31 @@ class Order(LockModel, LoggedModel):
             if position and position.attendee_email:
                 recipient = position.attendee_email
 
-            try:
-                email_content = render_mail(template, context)
-                subject = format_map(subject, context)
-                mail(
-                    recipient, subject, template, context,
-                    self.event, self.locale, self, headers=headers, sender=sender,
-                    invoices=invoices, attach_tickets=attach_tickets,
-                    position=position, auto_email=auto_email, attach_ical=attach_ical,
-                    attach_other_files=attach_other_files, attach_cached_files=attach_cached_files,
-                )
-            except SendMailException:
-                raise
-            else:
-                self.log_action(
-                    log_entry_type,
-                    user=user,
-                    auth=auth,
-                    data={
-                        'subject': subject,
-                        'message': email_content,
-                        'position': position.positionid if position else None,
-                        'recipient': recipient,
-                        'invoices': [i.pk for i in invoices] if invoices else [],
-                        'attach_tickets': attach_tickets,
-                        'attach_ical': attach_ical,
-                        'attach_other_files': attach_other_files,
-                        'attach_cached_files': [cf.filename for cf in attach_cached_files] if attach_cached_files else [],
-                    }
-                )
+            email_content = render_mail(template, context)
+            subject = format_map(subject, context)
+            mail(
+                recipient, subject, template, context,
+                self.event, self.locale, self, headers=headers, sender=sender,
+                invoices=invoices, attach_tickets=attach_tickets,
+                position=position, auto_email=auto_email, attach_ical=attach_ical,
+                attach_other_files=attach_other_files, attach_cached_files=attach_cached_files,
+            )
+            self.log_action(
+                log_entry_type,
+                user=user,
+                auth=auth,
+                data={
+                    'subject': subject,
+                    'message': email_content,
+                    'position': position.positionid if position else None,
+                    'recipient': recipient,
+                    'invoices': [i.pk for i in invoices] if invoices else [],
+                    'attach_tickets': attach_tickets,
+                    'attach_ical': attach_ical,
+                    'attach_other_files': attach_other_files,
+                    'attach_cached_files': [cf.filename for cf in attach_cached_files] if attach_cached_files else [],
+                }
+            )
 
     def resend_link(self, user=None, auth=None):
         with language(self.locale, self.event.settings.region):
@@ -1984,40 +1978,30 @@ class OrderPayment(models.Model):
             transmit_invoice.apply_async(args=(self.order.event_id, invoice.pk, False))
 
     def _send_paid_mail_attendee(self, position, user):
-        from pretix.base.services.mail import SendMailException
-
         with language(self.order.locale, self.order.event.settings.region):
             email_template = self.order.event.settings.mail_text_order_paid_attendee
             email_subject = self.order.event.settings.mail_subject_order_paid_attendee
             email_context = get_email_context(event=self.order.event, order=self.order, position=position)
-            try:
-                position.send_mail(
-                    email_subject, email_template, email_context,
-                    'pretix.event.order.email.order_paid', user,
-                    invoices=[],
-                    attach_tickets=True,
-                    attach_ical=self.order.event.settings.mail_attach_ical
-                )
-            except SendMailException:
-                logger.exception('Order paid email could not be sent')
+            position.send_mail(
+                email_subject, email_template, email_context,
+                'pretix.event.order.email.order_paid', user,
+                invoices=[],
+                attach_tickets=True,
+                attach_ical=self.order.event.settings.mail_attach_ical
+            )
 
     def _send_paid_mail(self, invoice, user, mail_text):
-        from pretix.base.services.mail import SendMailException
-
         with language(self.order.locale, self.order.event.settings.region):
             email_template = self.order.event.settings.mail_text_order_paid
             email_subject = self.order.event.settings.mail_subject_order_paid
             email_context = get_email_context(event=self.order.event, order=self.order, payment_info=mail_text)
-            try:
-                self.order.send_mail(
-                    email_subject, email_template, email_context,
-                    'pretix.event.order.email.order_paid', user,
-                    invoices=[invoice] if invoice else [],
-                    attach_tickets=True,
-                    attach_ical=self.order.event.settings.mail_attach_ical
-                )
-            except SendMailException:
-                logger.exception('Order paid email could not be sent')
+            self.order.send_mail(
+                email_subject, email_template, email_context,
+                'pretix.event.order.email.order_paid', user,
+                invoices=[invoice] if invoice else [],
+                attach_tickets=True,
+                attach_ical=self.order.event.settings.mail_attach_ical
+            )
 
     @property
     def refunded_amount(self):
@@ -2835,45 +2819,39 @@ class OrderPosition(AbstractPosition):
         :param attach_tickets: Attach tickets of this order, if they are existing and ready to download
         :param attach_ical: Attach relevant ICS files
         """
-        from pretix.base.services.mail import (
-            SendMailException, mail, render_mail,
-        )
+        from pretix.base.services.mail import mail, render_mail
 
         if not self.attendee_email:
             return
 
         with language(self.order.locale, self.order.event.settings.region):
             recipient = self.attendee_email
-            try:
-                email_content = render_mail(template, context)
-                subject = format_map(subject, context)
-                mail(
-                    recipient, subject, template, context,
-                    self.event, self.order.locale, order=self.order, headers=headers, sender=sender,
-                    position=self,
-                    invoices=invoices,
-                    attach_tickets=attach_tickets,
-                    attach_ical=attach_ical,
-                    attach_other_files=attach_other_files,
-                )
-            except SendMailException:
-                raise
-            else:
-                self.order.log_action(
-                    log_entry_type,
-                    user=user,
-                    auth=auth,
-                    data={
-                        'subject': subject,
-                        'message': email_content,
-                        'recipient': recipient,
-                        'invoices': [i.pk for i in invoices] if invoices else [],
-                        'attach_tickets': attach_tickets,
-                        'attach_ical': attach_ical,
-                        'attach_other_files': attach_other_files,
-                        'attach_cached_files': [],
-                    }
-                )
+            email_content = render_mail(template, context)
+            subject = format_map(subject, context)
+            mail(
+                recipient, subject, template, context,
+                self.event, self.order.locale, order=self.order, headers=headers, sender=sender,
+                position=self,
+                invoices=invoices,
+                attach_tickets=attach_tickets,
+                attach_ical=attach_ical,
+                attach_other_files=attach_other_files,
+            )
+            self.order.log_action(
+                log_entry_type,
+                user=user,
+                auth=auth,
+                data={
+                    'subject': subject,
+                    'message': email_content,
+                    'recipient': recipient,
+                    'invoices': [i.pk for i in invoices] if invoices else [],
+                    'attach_tickets': attach_tickets,
+                    'attach_ical': attach_ical,
+                    'attach_other_files': attach_other_files,
+                    'attach_cached_files': [],
+                }
+            )
 
     def resend_link(self, user=None, auth=None):
 

src/pretix/base/models/waitinglist.py

@@ -34,7 +34,7 @@ from phonenumber_field.modelfields import PhoneNumberField
 from pretix.base.email import get_email_context
 from pretix.base.i18n import language
 from pretix.base.models import User, Voucher
-from pretix.base.services.mail import SendMailException, mail, render_mail
+from pretix.base.services.mail import mail, render_mail
 
 from ...helpers.format import format_map
 from ...helpers.names import build_name
@@ -265,34 +265,30 @@ class WaitingListEntry(LoggedModel):
         with language(self.locale, self.event.settings.region):
             recipient = self.email
 
-            try:
-                email_content = render_mail(template, context)
-                subject = format_map(subject, context)
-                mail(
-                    recipient, subject, template, context,
-                    self.event,
-                    self.locale,
-                    headers=headers,
-                    sender=sender,
-                    auto_email=auto_email,
-                    attach_other_files=attach_other_files,
-                    attach_cached_files=attach_cached_files,
-                )
-            except SendMailException:
-                raise
-            else:
-                self.log_action(
-                    log_entry_type,
-                    user=user,
-                    auth=auth,
-                    data={
-                        'subject': subject,
-                        'message': email_content,
-                        'recipient': recipient,
-                        'attach_other_files': attach_other_files,
-                        'attach_cached_files': [cf.filename for cf in attach_cached_files] if attach_cached_files else [],
-                    }
-                )
+            email_content = render_mail(template, context)
+            subject = format_map(subject, context)
+            mail(
+                recipient, subject, template, context,
+                self.event,
+                self.locale,
+                headers=headers,
+                sender=sender,
+                auto_email=auto_email,
+                attach_other_files=attach_other_files,
+                attach_cached_files=attach_cached_files,
+            )
+            self.log_action(
+                log_entry_type,
+                user=user,
+                auth=auth,
+                data={
+                    'subject': subject,
+                    'message': email_content,
+                    'recipient': recipient,
+                    'attach_other_files': attach_other_files,
+                    'attach_cached_files': [cf.filename for cf in attach_cached_files] if attach_cached_files else [],
+                }
+            )
 
     @staticmethod
     def clean_itemvar(event, item, variation):

src/pretix/base/services/cancelevent.py

@@ -35,7 +35,7 @@ from pretix.base.models import (
     SubEvent, TaxRule, User, WaitingListEntry,
 )
 from pretix.base.services.locking import LockTimeoutException
-from pretix.base.services.mail import SendMailException, mail
+from pretix.base.services.mail import mail
 from pretix.base.services.orders import (
     OrderChangeManager, OrderError, _cancel_order, _try_auto_refund,
 )
@@ -51,17 +51,14 @@ logger = logging.getLogger(__name__)
 def _send_wle_mail(wle: WaitingListEntry, subject: LazyI18nString, message: LazyI18nString, subevent: SubEvent):
     with language(wle.locale, wle.event.settings.region):
         email_context = get_email_context(event_or_subevent=subevent or wle.event, event=wle.event)
-        try:
-            mail(
-                wle.email,
-                format_map(subject, email_context),
-                message,
-                email_context,
-                wle.event,
-                locale=wle.locale
-            )
-        except SendMailException:
-            logger.exception('Waiting list canceled email could not be sent')
+        mail(
+            wle.email,
+            format_map(subject, email_context),
+            message,
+            email_context,
+            wle.event,
+            locale=wle.locale
+        )
 
 
 def _send_mail(order: Order, subject: LazyI18nString, message: LazyI18nString, subevent: SubEvent,
@@ -75,14 +72,11 @@ def _send_mail(order: Order, subject: LazyI18nString, message: LazyI18nString, s
         email_context = get_email_context(event_or_subevent=subevent or order.event, refund_amount=refund_amount,
                                           order=order, position_or_address=ia, event=order.event)
         real_subject = format_map(subject, email_context)
-        try:
-            order.send_mail(
-                real_subject, message, email_context,
-                'pretix.event.order.email.event_canceled',
-                user,
-            )
-        except SendMailException:
-            logger.exception('Order canceled email could not be sent')
+        order.send_mail(
+            real_subject, message, email_context,
+            'pretix.event.order.email.event_canceled',
+            user,
+        )
 
         for p in positions:
             if subevent and p.subevent_id != subevent.id:
@@ -95,15 +89,12 @@ def _send_mail(order: Order, subject: LazyI18nString, message: LazyI18nString, s
                                                   refund_amount=refund_amount,
                                                   position_or_address=p,
                                                   order=order, position=p)
-                try:
-                    order.send_mail(
-                        real_subject, message, email_context,
-                        'pretix.event.order.email.event_canceled',
-                        position=p,
-                        user=user
-                    )
-                except SendMailException:
-                    logger.exception('Order canceled email could not be sent to attendee')
+                order.send_mail(
+                    real_subject, message, email_context,
+                    'pretix.event.order.email.event_canceled',
+                    position=p,
+                    user=user
+                )
 
 
 @app.task(base=ProfiledEventTask, bind=True, max_retries=5, default_retry_delay=1, throws=(OrderError,))

src/pretix/base/services/mail.py

@@ -42,7 +42,7 @@ import smtplib
 import warnings
 from email.mime.image import MIMEImage
 from email.utils import formataddr
-from typing import Any, Dict, List, Sequence, Union
+from typing import Any, Dict, Sequence, Union
 from urllib.parse import urljoin, urlparse
 from zoneinfo import ZoneInfo
 
@@ -52,16 +52,13 @@ from celery import chain
 from celery.exceptions import MaxRetriesExceededError
 from django.conf import settings
 from django.core.files.storage import default_storage
-from django.core.mail import (
-    EmailMultiAlternatives, SafeMIMEMultipart, get_connection,
-)
+from django.core.mail import EmailMultiAlternatives, SafeMIMEMultipart
 from django.core.mail.message import SafeMIMEText
 from django.db import transaction
 from django.template.loader import get_template
 from django.utils.html import escape
 from django.utils.timezone import now, override
 from django.utils.translation import gettext as _, pgettext
-from django_scopes import scope, scopes_disabled
 from i18nfield.strings import LazyI18nString
 from text_unidecode import unidecode
 
@@ -69,13 +66,15 @@ from pretix.base.email import ClassicMailRenderer
 from pretix.base.i18n import language
 from pretix.base.models import (
     CachedFile, Customer, Event, Invoice, InvoiceAddress, Order, OrderPosition,
-    Organizer, User,
+    Organizer,
 )
+from pretix.base.models.mail import OutgoingMail
 from pretix.base.services.invoices import invoice_pdf_task
 from pretix.base.services.tasks import TransactionAwareTask
 from pretix.base.services.tickets import get_tickets_for_order
 from pretix.base.signals import email_filter, global_email_filter
 from pretix.celery_app import app
+from pretix.helpers import OF_SELF
 from pretix.helpers.format import SafeFormatter, format_map
 from pretix.helpers.hierarkey import clean_filename
 from pretix.multidomain.urlreverse import build_absolute_uri
@@ -92,6 +91,9 @@ class TolerantDict(dict):
 
 
 class SendMailException(Exception):
+    """
+    Deprecated, not thrown any more.
+    """
     pass
 
 
@@ -203,161 +205,119 @@ def mail(email: Union[str, Sequence[str]], subject: str, template: Union[str, La
     if no_order_links and not plain_text_only:
         raise ValueError('If you set no_order_links, you also need to set plain_text_only.')
 
+    settings_holder = event or organizer
+
     headers = headers or {}
     if auto_email:
         headers['X-Auto-Response-Suppress'] = 'OOF, NRN, AutoReply, RN'
         headers['Auto-Submitted'] = 'auto-generated'
     headers.setdefault('X-Mailer', 'pretix')
 
+    bcc = list(bcc or [])
+    if settings_holder and settings_holder.settings.mail_bcc:
+        for bcc_mail in settings_holder.settings.mail_bcc.split(','):
+            bcc.append(bcc_mail.strip())
+
+    if (settings_holder
+            and settings_holder.settings.mail_from in (settings.DEFAULT_FROM_EMAIL, settings.MAIL_FROM_ORGANIZERS)
+            and settings_holder.settings.contact_mail and not headers.get('Reply-To')):
+        headers['Reply-To'] = settings_holder.settings.contact_mail
+
+    if settings_holder:
+        timezone = settings_holder.timezone
+    elif user:
+        timezone = ZoneInfo(user.timezone)
+    else:
+        timezone = ZoneInfo(settings.TIME_ZONE)
+
+    if event and attach_tickets and not event.settings.mail_attach_tickets:
+        attach_tickets = False
+
     with language(locale):
         if isinstance(context, dict) and order:
-            try:
-                context.update({
-                    'invoice_name': order.invoice_address.name,
-                    'invoice_company': order.invoice_address.company
-                })
-            except InvoiceAddress.DoesNotExist:
-                context.update({
-                    'invoice_name': '',
-                    'invoice_company': ''
-                })
-        renderer = ClassicMailRenderer(None, organizer)
-        content_plain = body_plain = render_mail(template, context)
-        subject = str(subject).format_map(TolerantDict(context))
-        sender = (
-            sender or
-            (event.settings.get('mail_from') if event else None) or
-            (organizer.settings.get('mail_from') if organizer else None) or
-            settings.MAIL_FROM
-        )
-        if event:
-            sender_name = clean_sender_name(event.settings.mail_from_name or str(event.name))
-            sender = formataddr((sender_name, sender))
-        elif organizer:
-            sender_name = clean_sender_name(organizer.settings.mail_from_name or str(organizer.name))
-            sender = formataddr((sender_name, sender))
-        else:
-            sender = formataddr((clean_sender_name(settings.PRETIX_INSTANCE_NAME), sender))
-
-        subject = raw_subject = str(subject).replace('\n', ' ').replace('\r', '')[:900]
-        signature = ""
-
-        bcc = list(bcc or [])
-
-        settings_holder = event or organizer
-
-        if event:
-            timezone = event.timezone
-        elif user:
-            timezone = ZoneInfo(user.timezone)
-        elif organizer:
-            timezone = organizer.timezone
-        else:
-            timezone = ZoneInfo(settings.TIME_ZONE)
+            _autoextend_context(context, order)
 
+        # Build raw content
+        content_plain = render_mail(template, context)
         if settings_holder:
-            if settings_holder.settings.mail_bcc:
-                for bcc_mail in settings_holder.settings.mail_bcc.split(','):
-                    bcc.append(bcc_mail.strip())
-
-            if settings_holder.settings.mail_from in (settings.DEFAULT_FROM_EMAIL, settings.MAIL_FROM_ORGANIZERS) \
-                    and settings_holder.settings.contact_mail and not headers.get('Reply-To'):
-                headers['Reply-To'] = settings_holder.settings.contact_mail
-
-            subject = prefix_subject(settings_holder, subject)
-
-            body_plain += "\r\n\r\n-- \r\n"
-
             signature = str(settings_holder.settings.get('mail_text_signature'))
-            if signature:
-                signature = signature.format(event=event.name if event else '')
-                body_plain += signature
-                body_plain += "\r\n\r\n-- \r\n"
-
-        if event:
-            renderer = event.get_html_mail_renderer()
-
-            if order and order.testmode:
-                subject = "[TESTMODE] " + subject
-
-            if order and position and not no_order_links:
-                body_plain += _(
-                    "You are receiving this email because someone placed an order for {event} for you."
-                ).format(event=event.name)
-                body_plain += "\r\n"
-                body_plain += _(
-                    "You can view your order details at the following URL:\n{orderurl}."
-                ).replace("\n", "\r\n").format(
-                    event=event.name, orderurl=build_absolute_uri(
-                        order.event, 'presale:event.order.position', kwargs={
-                            'order': order.code,
-                            'secret': position.web_secret,
-                            'position': position.positionid,
-                        }
-                    )
-                )
-            elif order and not no_order_links:
-                body_plain += _(
-                    "You are receiving this email because you placed an order for {event}."
-                ).format(event=event.name)
-                body_plain += "\r\n"
-                body_plain += _(
-                    "You can view your order details at the following URL:\n{orderurl}."
-                ).replace("\n", "\r\n").format(
-                    event=event.name, orderurl=build_absolute_uri(
-                        order.event, 'presale:event.order.open', kwargs={
-                            'order': order.code,
-                            'secret': order.secret,
-                            'hash': order.email_confirm_secret()
-                        }
-                    )
-                )
-            body_plain += "\r\n"
-
-        with override(timezone):
-            try:
-                if plain_text_only:
-                    body_html = None
-                elif 'context' in inspect.signature(renderer.render).parameters:
-                    body_html = renderer.render(content_plain, signature, raw_subject, order, position, context)
-                elif 'position' in inspect.signature(renderer.render).parameters:
-                    # Backwards compatibility
-                    warnings.warn('Email renderer called without context argument because context argument is not '
-                                  'supported.',
-                                  DeprecationWarning)
-                    body_html = renderer.render(content_plain, signature, raw_subject, order, position)
-                else:
-                    # Backwards compatibility
-                    warnings.warn('Email renderer called without position argument because position argument is not '
-                                  'supported.',
-                                  DeprecationWarning)
-                    body_html = renderer.render(content_plain, signature, raw_subject, order)
-            except:
-                logger.exception('Could not render HTML body')
-                body_html = None
+        else:
+            signature = ""
 
+        # Build full plain-text body
+        body_plain = _wrap_plain_body(content_plain, signature, event, order, position, no_order_links)
         body_plain = format_map(body_plain, context, mode=SafeFormatter.MODE_RICH_TO_PLAIN)
 
-        send_task = mail_send_task.si(
+        # Build subject
+        subject = str(subject).format_map(TolerantDict(context))
+        subject = raw_subject = subject.replace('\n', ' ').replace('\r', '')[:900]
+        if settings_holder:
+            subject = prefix_subject(settings_holder, subject)
+        if (order and order.testmode) or (not order and event and event.testmode):
+            subject = "[TESTMODE] " + subject
+
+        # Build sender
+        sender = _full_sender(sender, event, organizer)
+
+        # Build HTML body
+        if plain_text_only:
+            body_html = None
+        else:
+            if event:
+                renderer = event.get_html_mail_renderer()
+            else:
+                renderer = ClassicMailRenderer(None, organizer)
+
+            with override(timezone):
+                try:
+                    if 'context' in inspect.signature(renderer.render).parameters:
+                        body_html = renderer.render(content_plain, signature, raw_subject, order, position, context)
+                    elif 'position' in inspect.signature(renderer.render).parameters:
+                        # Backwards compatibility
+                        warnings.warn('Email renderer called without context argument because context argument is not '
+                                      'supported.',
+                                      DeprecationWarning)
+                        body_html = renderer.render(content_plain, signature, raw_subject, order, position)
+                    else:
+                        # Backwards compatibility
+                        warnings.warn('Email renderer called without position argument because position argument is not '
+                                      'supported.',
+                                      DeprecationWarning)
+                        body_html = renderer.render(content_plain, signature, raw_subject, order)
+                except:
+                    logger.exception('Could not render HTML body')
+                    body_html = None
+
+        m = OutgoingMail.objects.create(
+            organizer=organizer,
+            event=event,
+            order=order,
+            orderposition=position,
+            customer=customer,
+            user=user,
             to=[email] if isinstance(email, str) else list(email),
-            cc=cc,
-            bcc=bcc,
+            cc=cc or [],
+            bcc=bcc or [],
             subject=subject,
-            body=body_plain,
-            html=body_html,
+            body_plain=body_plain,
+            body_html=body_html,
             sender=sender,
-            event=event.id if event else None,
             headers=headers,
-            invoices=[i.pk for i in invoices] if invoices and not position else [],
-            order=order.pk if order else None,
-            position=position.pk if position else None,
-            attach_tickets=attach_tickets,
-            attach_ical=attach_ical,
-            user=user.pk if user else None,
-            organizer=organizer.pk if organizer else None,
-            customer=customer.pk if customer else None,
-            attach_cached_files=[(cf.id if isinstance(cf, CachedFile) else cf) for cf in attach_cached_files] if attach_cached_files else [],
-            attach_other_files=attach_other_files,
+            should_attach_tickets=attach_tickets,
+            should_attach_ical=attach_ical,
+            should_attach_other_files=attach_other_files or [],
+        )
+        if invoices and not position:
+            m.should_attach_invoices.add(*invoices)
+        if attach_cached_files:
+            for cf in attach_cached_files:
+                if not isinstance(cf, CachedFile):
+                    m.should_attach_cached_files.add(CachedFile.objects.get(pk=cf))
+                else:
+                    m.should_attach_cached_files.add(cf)
+
+        send_task = mail_send_task.si(
+            outgoing_mail=m.id
         )
 
         if invoices:
@@ -392,176 +352,177 @@ class CustomEmail(EmailMultiAlternatives):
 
 
 @app.task(base=TransactionAwareTask, bind=True, acks_late=True)
-def mail_send_task(self, *args, to: List[str], subject: str, body: str, html: str, sender: str,
-                   event: int = None, position: int = None, headers: dict = None, cc: List[str] = None, bcc: List[str] = None,
-                   invoices: List[int] = None, order: int = None, attach_tickets=False, user=None,
-                   organizer=None, customer=None, attach_ical=False, attach_cached_files: List[int] = None,
-                   attach_other_files: List[str] = None) -> bool:
-    email = CustomEmail(subject, body, sender, to=to, cc=cc, bcc=bcc, headers=headers)
-    if html is not None:
+def mail_send_task(self, *args, outgoing_mail: int) -> bool:
+    with transaction.atomic():
+        outgoing_mail = OutgoingMail.objects.select_for_update(of=OF_SELF).get(pk=outgoing_mail)
+        if outgoing_mail.status == OutgoingMail.STATUS_INFLIGHT:
+            logger.info("Ignoring job for inflight email")
+            return False
+        elif outgoing_mail.status in (OutgoingMail.STATUS_SENT, OutgoingMail.STATUS_FAILED):
+            logger.info(f"Ignoring job for email in final state {outgoing_mail.status}")
+            return False
+        outgoing_mail.status = OutgoingMail.STATUS_INFLIGHT
+        outgoing_mail.save(update_fields=["status"])
+
+    email = CustomEmail(
+        subject=outgoing_mail.subject,
+        body=outgoing_mail.body_plain,
+        from_email=outgoing_mail.sender,
+        to=outgoing_mail.to,
+        cc=outgoing_mail.cc,
+        bcc=outgoing_mail.bcc,
+        headers=outgoing_mail.headers,
+    )
+
+    # Rewrite all <img> tags from real URLs or data URLs to inline attachments refered to by content ID
+    if outgoing_mail.body_html is not None:
         html_message = SafeMIMEMultipart(_subtype='related', encoding=settings.DEFAULT_CHARSET)
-        html_with_cid, cid_images = replace_images_with_cid_paths(html)
+        html_with_cid, cid_images = replace_images_with_cid_paths(outgoing_mail.body_html)
         html_message.attach(SafeMIMEText(html_with_cid, 'html', settings.DEFAULT_CHARSET))
         attach_cid_images(html_message, cid_images, verify_ssl=True)
         email.attach_alternative(html_message, "multipart/related")
 
-    log_target = None
+    log_target, error_log_action_type = outgoing_mail.log_parameters()
+    invoices_attached = []
+    actual_attachments = []
 
-    if user:
-        user = User.objects.get(pk=user)
-        error_log_action_type = 'pretix.user.email.error'
-        log_target = user
-
-    if event:
-        with scopes_disabled():
-            event = Event.objects.get(id=event)
-            organizer = event.organizer
-        backend = event.get_mail_backend()
-        cm = lambda: scope(organizer=event.organizer)  # noqa
-    elif organizer:
-        with scopes_disabled():
-            organizer = Organizer.objects.get(id=organizer)
-        backend = organizer.get_mail_backend()
-        cm = lambda: scope(organizer=organizer)  # noqa
-    else:
-        backend = get_connection(fail_silently=False)
-        cm = lambda: scopes_disabled()  # noqa
-
-    with cm():
-        if customer:
-            customer = Customer.objects.get(pk=customer)
-            if not user:
-                error_log_action_type = 'pretix.customer.email.error'
-                log_target = customer
-
-        if event:
-            if order:
-                try:
-                    order = event.orders.get(pk=order)
-                    error_log_action_type = 'pretix.event.order.email.error'
-                    log_target = order
-                except Order.DoesNotExist:
-                    order = None
-                else:
-                    with language(order.locale, event.settings.region):
-                        if not event.settings.mail_attach_tickets:
-                            attach_tickets = False
-                        if position:
-                            try:
-                                position = order.positions.get(pk=position)
-                            except OrderPosition.DoesNotExist:
-                                attach_tickets = False
-                        if attach_tickets:
-                            args = []
-                            attach_size = 0
-                            for name, ct in get_tickets_for_order(order, base_position=position):
-                                try:
-                                    content = ct.file.read()
-                                    args.append((name, content, ct.type))
-                                    attach_size += len(content)
-                                except:
-                                    # This sometimes fails e.g. with FileNotFoundError. We haven't been able to figure out
-                                    # why (probably some race condition with ticket cache invalidation?), so retry later.
-                                    try:
-                                        self.retry(max_retries=5, countdown=60)
-                                    except MaxRetriesExceededError:
-                                        # Well then, something is really wrong, let's send it without attachment before we
-                                        # don't sent at all
-                                        logger.exception('Could not attach invoice to email')
-                                        pass
-
-                            if attach_size < settings.FILE_UPLOAD_MAX_SIZE_EMAIL_ATTACHMENT - 1:
-                                # Do not attach more than (limit - 1 MB) in tickets (1MB space for invoice, email itself, …),
-                                # it will bounce way to often.
-                                for a in args:
-                                    try:
-                                        email.attach(*a)
-                                    except:
-                                        pass
-                            else:
-                                order.log_action(
-                                    'pretix.event.order.email.attachments.skipped',
-                                    data={
-                                        'subject': 'Attachments skipped',
-                                        'message': 'Attachment have not been send because {} bytes are likely too large to arrive.'.format(attach_size),
-                                        'recipient': '',
-                                        'invoices': [],
-                                    }
-                                )
-                        if attach_ical:
-                            fname = re.sub('[^a-zA-Z0-9 ]', '-', unidecode(pgettext('attachment_filename', 'Calendar invite')))
-                            for i, cal in enumerate(get_private_icals(event, [position] if position else order.positions.all())):
-                                email.attach('{}{}.ics'.format(fname, f'-{i + 1}' if i > 0 else ''), cal.serialize(), 'text/calendar')
-
-            email = email_filter.send_chained(event, 'message', message=email, order=order, user=user)
-
-        invoices_sent = []
-        if invoices:
-            invoices = Invoice.objects.filter(pk__in=invoices)
-            for inv in invoices:
-                if inv.file:
+    with outgoing_mail.scope_manager():
+        # Attach tickets
+        if outgoing_mail.should_attach_tickets and outgoing_mail.order:
+            with language(outgoing_mail.order.locale, outgoing_mail.event.settings.region):
+                args = []
+                attach_size = 0
+                for name, ct in get_tickets_for_order(outgoing_mail.order, base_position=outgoing_mail.orderposition):
                     try:
-                        # We try to give the invoice a more human-readable name, e.g. "Invoice_ABC-123.pdf" instead of
-                        # just "ABC-123.pdf", but we only do so if our currently selected language allows to do this
-                        # as ASCII text. For example, we would not want a "فاتورة_" prefix for our filename since this
-                        # has shown to cause deliverability problems of the email and deliverability wins.
-                        with language(order.locale if order else inv.locale, event.settings.region if event else None):
-                            filename = pgettext('invoice', 'Invoice {num}').format(num=inv.number).replace(' ', '_') + '.pdf'
-                        if not re.match("^[a-zA-Z0-9-_%./,&:# ]+$", filename):
-                            filename = inv.number.replace(' ', '_') + '.pdf'
-                        filename = re.sub("[^a-zA-Z0-9-_.]+", "_", filename)
-                        with language(inv.order.locale):
-                            email.attach(
-                                filename,
-                                inv.file.file.read(),
-                                'application/pdf'
-                            )
-                        invoices_sent.append(inv)
+                        content = ct.file.read()
+                        args.append((name, content, ct.type))
+                        attach_size += len(content)
                     except:
-                        logger.exception('Could not attach invoice to email')
-                        pass
+                        # This sometimes fails e.g. with FileNotFoundError. We haven't been able to figure out
+                        # why (probably some race condition with ticket cache invalidation?), so retry later.
+                        try:
+                            self.retry(max_retries=5, countdown=60)
+                        except MaxRetriesExceededError:
+                            # Well then, something is really wrong, let's send it without attachment before we
+                            # don't sent at all
+                            logger.exception('Could not attach invoice to email')
+                            pass
 
-        if attach_other_files:
-            for fname in attach_other_files:
-                ftype, _ = mimetypes.guess_type(fname)
-                data = default_storage.open(fname).read()
+                if attach_size < settings.FILE_UPLOAD_MAX_SIZE_EMAIL_ATTACHMENT - 1:
+                    # Do not attach more than (limit - 1 MB) in tickets (1MB space for invoice, email itself, …),
+                    # it will bounce way to often.
+                    for a in args:
+                        try:
+                            email.attach(*a)
+                        except:
+                            pass
+                else:
+                    outgoing_mail.order.log_action(
+                        'pretix.event.order.email.attachments.skipped',
+                        data={
+                            'subject': 'Attachments skipped',
+                            'message': 'Attachment have not been send because {} bytes are likely too large to arrive.'.format(attach_size),
+                            'recipient': '',
+                            'invoices': [],
+                        }
+                    )
+
+        # Attach calendar files
+        if outgoing_mail.should_attach_ical and outgoing_mail.order:
+            fname = re.sub('[^a-zA-Z0-9 ]', '-', unidecode(pgettext('attachment_filename', 'Calendar invite')))
+            icals = get_private_icals(
+                outgoing_mail.event,
+                [outgoing_mail.orderposition] if outgoing_mail.orderposition else outgoing_mail.order.positions.all()
+            )
+            for i, cal in enumerate(icals):
+                name = '{}{}.ics'.format(fname, f'-{i + 1}' if i > 0 else '')
+                content = cal.serialize()
+                mimetype = 'text/calendar'
+                email.attach(name, content, mimetype)
+
+        for inv in outgoing_mail.should_attach_invoices.all():
+            if inv.file:
+                try:
+                    # We try to give the invoice a more human-readable name, e.g. "Invoice_ABC-123.pdf" instead of
+                    # just "ABC-123.pdf", but we only do so if our currently selected language allows to do this
+                    # as ASCII text. For example, we would not want a "فاتورة_" prefix for our filename since this
+                    # has shown to cause deliverability problems of the email and deliverability wins.
+                    with language(outgoing_mail.order.locale if outgoing_mail.order else inv.locale, outgoing_mail.event.settings.region):
+                        filename = pgettext('invoice', 'Invoice {num}').format(num=inv.number).replace(' ', '_') + '.pdf'
+                    if not re.match("^[a-zA-Z0-9-_%./,&:# ]+$", filename):
+                        filename = inv.number.replace(' ', '_') + '.pdf'
+                    filename = re.sub("[^a-zA-Z0-9-_.]+", "_", filename)
+                    content = inv.file.file.read()
+                    with language(inv.order.locale):
+                        email.attach(
+                            filename,
+                            content,
+                            'application/pdf'
+                        )
+                    invoices_attached.append(inv)
+                except:
+                    logger.exception('Could not attach invoice to email')
+                    pass
+
+        for fname in outgoing_mail.should_attach_other_files:
+            ftype, _ = mimetypes.guess_type(fname)
+            data = default_storage.open(fname).read()
+            try:
+                email.attach(
+                    clean_filename(os.path.basename(fname)),
+                    data,
+                    ftype
+                )
+            except:
+                logger.exception('Could not attach file to email')
+                pass
+
+        for cf in outgoing_mail.should_attach_cached_files.all():
+            if cf.file:
                 try:
                     email.attach(
-                        clean_filename(os.path.basename(fname)),
-                        data,
-                        ftype
+                        cf.filename,
+                        cf.file.file.read(),
+                        cf.type,
                     )
                 except:
                     logger.exception('Could not attach file to email')
                     pass
 
-        if attach_cached_files:
-            for cf in CachedFile.objects.filter(id__in=attach_cached_files):
-                if cf.file:
-                    try:
-                        email.attach(
-                            cf.filename,
-                            cf.file.file.read(),
-                            cf.type,
-                        )
-                    except:
-                        logger.exception('Could not attach file to email')
-                        pass
+        if outgoing_mail.event:
+            with outgoing_mail.scope_manager():
+                email = email_filter.send_chained(
+                    outgoing_mail.event, 'message', message=email, order=outgoing_mail.order, user=outgoing_mail.user
+                )
 
-        email = global_email_filter.send_chained(event, 'message', message=email, user=user, order=order,
-                                                 organizer=organizer, customer=customer)
+        email = global_email_filter.send_chained(
+            outgoing_mail.event, 'message', message=email, user=outgoing_mail.user, order=outgoing_mail.order,
+            organizer=outgoing_mail.organizer, customer=outgoing_mail.customer
+        )
 
+        outgoing_mail.actual_attachments = [
+            {
+                "name": a[0],
+                "size": len(a[1]),
+                "type": a[2],
+            } for a in email.attachments
+        ]
+
+        backend = outgoing_mail.get_mail_backend()
         try:
             backend.send_messages([email])
-        except (smtplib.SMTPResponseException, smtplib.SMTPSenderRefused) as e:
-            if e.smtp_code in (101, 111, 421, 422, 431, 432, 442, 447, 452):
-                if e.smtp_code == 432 and settings.HAS_REDIS:
-                    # This is likely Microsoft Exchange Online which has a pretty bad rate limit of max. 3 concurrent
-                    # SMTP connections which is *easily* exceeded with many celery threads. Just retrying with exponential
-                    # backoff won't be good enough if we have a lot of emails, instead we'll need to make sure our retry
-                    # intervals scatter such that the email won't all be retried at the same time again and cause the
-                    # same problem.
-                    # See also https://docs.microsoft.com/en-us/exchange/troubleshoot/send-emails/smtp-submission-improvements
+        except Exception as e:
+            logger.exception('Error sending email')
+            retry_strategy = _retry_strategy(e)
+            err, err_detail = _format_error(e)
+
+            outgoing_mail.error = err
+            outgoing_mail.error_detail = err_detail
+            outgoing_mail.sent = now()
+
+            # Run retries
+            try:
+                if retry_strategy == "microsoft_concurrency" and settings.HAS_REDIS:
                     from django_redis import get_redis_connection
 
                     redis_key = "pretix_mail_retry_" + hashlib.sha1(f"{getattr(backend, 'username', '_')}@{getattr(backend, 'host', '_')}".encode()).hexdigest()
@@ -571,100 +532,59 @@ def mail_send_task(self, *args, to: List[str], subject: str, body: str, html: st
 
                     max_retries = 10
                     retry_after = min(30 + cnt * 10, 1800)
-                else:
-                    # Most likely some other kind of temporary failure, retry again (but pretty soon)
+
+                    outgoing_mail.status = OutgoingMail.STATUS_AWAWITING_RETRY
+                    outgoing_mail.save(upate_fields=["status", "error", "error_detail", "sent"])
+                    self.retry(max_retries=max_retries, countdown=retry_after)  # throws RetryException, ends function flow
+                elif retry_strategy in ("microsoft_concurrency", "quick"):
                     max_retries = 5
                     retry_after = [10, 30, 60, 300, 900, 900][self.request.retries]
+                    outgoing_mail.status = OutgoingMail.STATUS_AWAWITING_RETRY
+                    outgoing_mail.save(upate_fields=["status", "error", "error_detail", "sent"])
+                    self.retry(max_retries=max_retries, countdown=retry_after)  # throws RetryException, ends function flow
 
-                try:
-                    self.retry(max_retries=max_retries, countdown=retry_after)
-                except MaxRetriesExceededError:
-                    if log_target:
-                        log_target.log_action(
-                            error_log_action_type,
-                            data={
-                                'subject': 'SMTP code {}, max retries exceeded'.format(e.smtp_code),
-                                'message': e.smtp_error.decode() if isinstance(e.smtp_error, bytes) else str(e.smtp_error),
-                                'recipient': '',
-                                'invoices': [],
-                            }
-                        )
-                    raise e
+                elif retry_strategy == "slow":
+                    outgoing_mail.status = OutgoingMail.STATUS_AWAWITING_RETRY
+                    outgoing_mail.save(upate_fields=["status", "error", "error_detail", "sent"])
+                    self.retry(max_retries=5, countdown=[60, 300, 600, 1200, 1800, 1800][self.request.retries])  # throws RetryException, ends function flow
 
-            logger.exception('Error sending email')
+            except MaxRetriesExceededError:
+                if log_target:
+                    log_target.log_action(
+                        error_log_action_type,
+                        data={
+                            'subject': f'{err} (max retries exceeded)',
+                            'message': err_detail,
+                            'recipient': '',
+                            'invoices': [],
+                        }
+                    )
+                return False
+
+            # If we reach this, it's a non-retryable error
+            outgoing_mail.status = OutgoingMail.STATUS_FAILED
+            outgoing_mail.sent = now()
+            outgoing_mail.save(upate_fields=["status", "error", "error_detail", "sent"])
             if log_target:
                 log_target.log_action(
                     error_log_action_type,
                     data={
-                        'subject': 'SMTP code {}'.format(e.smtp_code),
-                        'message': e.smtp_error.decode() if isinstance(e.smtp_error, bytes) else str(e.smtp_error),
+                        'subject': err,
+                        'message': err_detail,
                         'recipient': '',
                         'invoices': [],
                     }
                 )
-
-            raise SendMailException('Failed to send an email to {}.'.format(to))
-        except smtplib.SMTPRecipientsRefused as e:
-            smtp_codes = [a[0] for a in e.recipients.values()]
-
-            if not any(c >= 500 for c in smtp_codes) or any(b'Message is too large' in a[1] for a in e.recipients.values()):
-                # This is not a permanent failure (mailbox full, service unavailable), retry later, but with large
-                # intervals. One would think that "Message is too lage" is a permanent failure, but apparently it is not.
-                # We have documented cases of emails to Microsoft returning the error occasionally and then later
-                # allowing the very same email.
-                try:
-                    self.retry(max_retries=5, countdown=[60, 300, 600, 1200, 1800, 1800][self.request.retries])
-                except MaxRetriesExceededError:
-                    # ignore and go on with logging the error
-                    pass
-
-            logger.exception('Error sending email')
-            if log_target:
-                message = []
-                for e, val in e.recipients.items():
-                    message.append(f'{e}: {val[0]} {val[1].decode()}')
-
-                log_target.log_action(
-                    error_log_action_type,
-                    data={
-                        'subject': 'SMTP error',
-                        'message': '\n'.join(message),
-                        'recipient': '',
-                        'invoices': [],
-                    }
-                )
-
-            raise SendMailException('Failed to send an email to {}.'.format(to))
-        except Exception as e:
-            if isinstance(e, OSError) and not isinstance(e, smtplib.SMTPNotSupportedError):
-                try:
-                    self.retry(max_retries=5, countdown=[10, 30, 60, 300, 900, 900][self.request.retries])
-                except MaxRetriesExceededError:
-                    if log_target:
-                        log_target.log_action(
-                            error_log_action_type,
-                            data={
-                                'subject': 'Internal error',
-                                'message': f'Max retries exceeded after error "{str(e)}"',
-                                'recipient': '',
-                                'invoices': [],
-                            }
-                        )
-                    raise e
-            if log_target:
-                log_target.log_action(
-                    error_log_action_type,
-                    data={
-                        'subject': 'Internal error',
-                        'message': str(e),
-                        'recipient': '',
-                        'invoices': [],
-                    }
-                )
-            logger.exception('Error sending email')
-            raise SendMailException('Failed to send an email to {}.'.format(to))
+            return False
         else:
-            for i in invoices_sent:
+            outgoing_mail.status = OutgoingMail.STATUS_SENT
+            outgoing_mail.error = None
+            outgoing_mail.error_detail = None
+            outgoing_mail.actual_attachments = actual_attachments
+            outgoing_mail.sent = now()
+            outgoing_mail.save(upate_fields=["status", "error", "error_detail", "sent", "actual_attachments"])
+
+            for i in invoices_attached:
                 if i.transmission_type == "email":
                     # Mark invoice as sent when it was sent to the requested address *either* at the time of invoice
                     # creation *or* as of right now.
@@ -675,7 +595,7 @@ def mail_send_task(self, *args, to: List[str], subject: str, body: str, html: st
                         expected_recipients.append((i.order.invoice_address.transmission_info or {}).get("transmission_email_address") or i.order.email)
                     except InvoiceAddress.DoesNotExist:
                         pass
-                    if not any(t in expected_recipients for t in to):
+                    if not any(t in expected_recipients for t in outgoing_mail.to):
                         continue
                     if i.transmission_status != Invoice.TRANSMISSION_STATUS_COMPLETED:
                         i.transmission_date = now()
@@ -684,7 +604,7 @@ def mail_send_task(self, *args, to: List[str], subject: str, body: str, html: st
                         i.transmission_info = {
                             "sent": [
                                 {
-                                    "recipients": to,
+                                    "recipients": outgoing_mail.to,
                                     "datetime": now().isoformat(),
                                 }
                             ]
@@ -696,7 +616,7 @@ def mail_send_task(self, *args, to: List[str], subject: str, body: str, html: st
                     elif i.transmission_provider == "email_pdf":
                         i.transmission_info["sent"].append(
                             {
-                                "recipients": to,
+                                "recipients": outgoing_mail.to,
                                 "datetime": now().isoformat(),
                             }
                         )
@@ -710,7 +630,7 @@ def mail_send_task(self, *args, to: List[str], subject: str, body: str, html: st
                             "transmission_provider": "email_pdf",
                             "transmission_type": "email",
                             "data": {
-                                "recipients": [to],
+                                "recipients": outgoing_mail.to,
                             },
                         }
                     )
@@ -833,3 +753,121 @@ def normalize_image_url(url):
         else:
             url = urljoin(settings.MEDIA_URL, url)
     return url
+
+
+def _autoextend_context(context, order):
+    try:
+        context.update({
+            'invoice_name': order.invoice_address.name,
+            'invoice_company': order.invoice_address.company
+        })
+    except InvoiceAddress.DoesNotExist:
+        context.update({
+            'invoice_name': '',
+            'invoice_company': ''
+        })
+
+
+def _full_sender(sender_address, event, organizer):
+    sender_address = (
+        sender_address or
+        (event.settings.get('mail_from') if event else None) or
+        (organizer.settings.get('mail_from') if organizer else None) or
+        settings.MAIL_FROM
+    )
+    if event:
+        sender_name = event.settings.mail_from_name or str(event.name)
+    elif organizer:
+        sender_name = organizer.settings.mail_from_name or str(organizer.name)
+    else:
+        sender_name = settings.PRETIX_INSTANCE_NAME
+
+    sender = formataddr((clean_sender_name(sender_name), sender_address))
+    return sender
+
+
+def _wrap_plain_body(content_plain, signature, event, order, position, no_order_links):
+    body_plain = content_plain
+    body_plain += "\r\n\r\n-- \r\n"
+
+    if signature:
+        signature = signature.format(event=event.name if event else '')
+        body_plain += signature
+        body_plain += "\r\n\r\n-- \r\n"
+
+    if event and order and position and not no_order_links:
+        body_plain += _(
+            "You are receiving this email because someone placed an order for {event} for you."
+        ).format(event=event.name)
+        body_plain += "\r\n"
+        body_plain += _(
+            "You can view your order details at the following URL:\n{orderurl}."
+        ).replace("\n", "\r\n").format(
+            event=event.name, orderurl=build_absolute_uri(
+                order.event, 'presale:event.order.position', kwargs={
+                    'order': order.code,
+                    'secret': position.web_secret,
+                    'position': position.positionid,
+                }
+            )
+        )
+    elif event and order and not no_order_links:
+        body_plain += _(
+            "You are receiving this email because you placed an order for {event}."
+        ).format(event=event.name)
+        body_plain += "\r\n"
+        body_plain += _(
+            "You can view your order details at the following URL:\n{orderurl}."
+        ).replace("\n", "\r\n").format(
+            event=event.name, orderurl=build_absolute_uri(
+                order.event, 'presale:event.order.open', kwargs={
+                    'order': order.code,
+                    'secret': order.secret,
+                    'hash': order.email_confirm_secret()
+                }
+            )
+        )
+    body_plain += "\r\n"
+
+    return body_plain
+
+
+def _retry_strategy(e: Exception):
+    if isinstance(e, (smtplib.SMTPResponseException, smtplib.SMTPSenderRefused)):
+        if e.smtp_code == 432:
+            # This is likely Microsoft Exchange Online which has a pretty bad rate limit of max. 3 concurrent
+            # SMTP connections which is *easily* exceeded with many celery threads. Just retrying with exponential
+            # backoff won't be good enough if we have a lot of emails, instead we'll need to make sure our retry
+            # intervals scatter such that the email won't all be retried at the same time again and cause the
+            # same problem.
+            # See also https://docs.microsoft.com/en-us/exchange/troubleshoot/send-emails/smtp-submission-improvements
+            return "microsoft_concurrncy"
+
+        if e.smtp_code in (101, 111, 421, 422, 431, 432, 442, 447, 452):
+            return "quick"
+
+    elif isinstance(e, smtplib.SMTPRecipientsRefused):
+        smtp_codes = [a[0] for a in e.recipients.values()]
+
+        if not any(c >= 500 for c in smtp_codes) or any(b'Message is too large' in a[1] for a in e.recipients.values()):
+            # This is not a permanent failure (mailbox full, service unavailable), retry later, but with large
+            # intervals. One would think that "Message is too lage" is a permanent failure, but apparently it is not.
+            # We have documented cases of emails to Microsoft returning the error occasionally and then later
+            # allowing the very same email.
+            return "slow"
+
+    elif isinstance(e, OSError) and not isinstance(e, smtplib.SMTPNotSupportedError):
+        # Most likely some other kind of temporary failure, retry again (but pretty soon)
+        return "quick"
+
+
+def _format_error(e: Exception):
+    if isinstance(e, (smtplib.SMTPResponseException, smtplib.SMTPSenderRefused)):
+        return 'SMTP code {}'.format(e.smtp_code), e.smtp_error.decode() if isinstance(e.smtp_error, bytes) else str(e.smtp_error)
+    elif isinstance(e, smtplib.SMTPRecipientsRefused):
+        message = []
+        for e, val in e.recipients.items():
+            message.append(f'{e}: {val[0]} {val[1].decode()}')
+        return 'SMTP recipients refudes', '\n'.join(message)
+    else:
+        return 'Internal error', str(e)

src/pretix/base/services/orders.py

@@ -90,7 +90,6 @@ from pretix.base.services.invoices import (
 from pretix.base.services.locking import (
     LOCK_TRUST_WINDOW, LockTimeoutException, lock_objects,
 )
-from pretix.base.services.mail import SendMailException
 from pretix.base.services.memberships import (
     create_membership, validate_memberships_in_order,
 )
@@ -421,33 +420,27 @@ def approve_order(order, user=None, send_mail: bool=True, auth=None, force=False
                 email_attendee_subject = order.event.settings.mail_subject_order_approved_attendee
 
             email_context = get_email_context(event=order.event, order=order)
-            try:
-                order.send_mail(
-                    email_subject, email_template, email_context,
-                    'pretix.event.order.email.order_approved', user,
-                    attach_tickets=True,
-                    attach_ical=order.event.settings.mail_attach_ical and (
-                        not order.event.settings.mail_attach_ical_paid_only or
-                        order.total == Decimal('0.00') or
-                        order.valid_if_pending
-                    ),
-                    invoices=[invoice] if invoice and transmit_invoice_mail else []
-                )
-            except SendMailException:
-                logger.exception('Order approved email could not be sent')
+            order.send_mail(
+                email_subject, email_template, email_context,
+                'pretix.event.order.email.order_approved', user,
+                attach_tickets=True,
+                attach_ical=order.event.settings.mail_attach_ical and (
+                    not order.event.settings.mail_attach_ical_paid_only or
+                    order.total == Decimal('0.00') or
+                    order.valid_if_pending
+                ),
+                invoices=[invoice] if invoice and transmit_invoice_mail else []
+            )
 
             if email_attendees:
                 for p in order.positions.all():
                     if p.addon_to_id is None and p.attendee_email and p.attendee_email != order.email:
                         email_attendee_context = get_email_context(event=order.event, order=order, position=p)
-                        try:
-                            p.send_mail(
-                                email_attendee_subject, email_attendee_template, email_attendee_context,
-                                'pretix.event.order.email.order_approved', user,
-                                attach_tickets=True,
-                            )
-                        except SendMailException:
-                            logger.exception('Order approved email could not be sent to attendee')
+                        p.send_mail(
+                            email_attendee_subject, email_attendee_template, email_attendee_context,
+                            'pretix.event.order.email.order_approved', user,
+                            attach_tickets=True,
+                        )
 
     return order.pk
 
@@ -484,13 +477,10 @@ def deny_order(order, comment='', user=None, send_mail: bool=True, auth=None):
             email_template = order.event.settings.mail_text_order_denied
             email_subject = order.event.settings.mail_subject_order_denied
             email_context = get_email_context(event=order.event, order=order, comment=comment)
-            try:
-                order.send_mail(
-                    email_subject, email_template, email_context,
-                    'pretix.event.order.email.order_denied', user
-                )
-            except SendMailException:
-                logger.exception('Order denied email could not be sent')
+            order.send_mail(
+                email_subject, email_template, email_context,
+                'pretix.event.order.email.order_denied', user
+            )
 
     return order.pk
 
@@ -637,14 +627,11 @@ def _cancel_order(order, user=None, send_mail: bool=True, api_token=None, device
                 email_template = order.event.settings.mail_text_order_canceled
                 email_subject = order.event.settings.mail_subject_order_canceled
                 email_context = get_email_context(event=order.event, order=order, comment=comment or "")
-                try:
-                    order.send_mail(
-                        email_subject, email_template, email_context,
-                        'pretix.event.order.email.order_canceled', user,
-                        invoices=transmit_invoices_mail,
-                    )
-                except SendMailException:
-                    logger.exception('Order canceled email could not be sent')
+                order.send_mail(
+                    email_subject, email_template, email_context,
+                    'pretix.event.order.email.order_canceled', user,
+                    invoices=transmit_invoices_mail,
+                )
 
     for p in order.payments.filter(state__in=(OrderPayment.PAYMENT_STATE_CREATED, OrderPayment.PAYMENT_STATE_PENDING)):
         try:
@@ -1099,46 +1086,40 @@ def _order_placed_email(event: Event, order: Order, email_template, subject_temp
                         log_entry: str, invoice, payments: List[OrderPayment], is_free=False):
     email_context = get_email_context(event=event, order=order, payments=payments)
 
-    try:
-        order.send_mail(
-            subject_template, email_template, email_context,
-            log_entry,
-            invoices=[invoice] if invoice else [],
-            attach_tickets=True,
-            attach_ical=event.settings.mail_attach_ical and (
-                not event.settings.mail_attach_ical_paid_only or
-                is_free or
-                order.valid_if_pending
-            ),
-            attach_other_files=[a for a in [
-                event.settings.get('mail_attachment_new_order', as_type=str, default='')[len('file://'):]
-            ] if a],
-        )
-    except SendMailException:
-        logger.exception('Order received email could not be sent')
+    order.send_mail(
+        subject_template, email_template, email_context,
+        log_entry,
+        invoices=[invoice] if invoice else [],
+        attach_tickets=True,
+        attach_ical=event.settings.mail_attach_ical and (
+            not event.settings.mail_attach_ical_paid_only or
+            is_free or
+            order.valid_if_pending
+        ),
+        attach_other_files=[a for a in [
+            event.settings.get('mail_attachment_new_order', as_type=str, default='')[len('file://'):]
+        ] if a],
+    )
 
 
 def _order_placed_email_attendee(event: Event, order: Order, position: OrderPosition, email_template, subject_template,
                                  log_entry: str, is_free=False):
     email_context = get_email_context(event=event, order=order, position=position)
 
-    try:
-        position.send_mail(
-            subject_template, email_template, email_context,
-            log_entry,
-            invoices=[],
-            attach_tickets=True,
-            attach_ical=event.settings.mail_attach_ical and (
-                not event.settings.mail_attach_ical_paid_only or
-                is_free or
-                order.valid_if_pending
-            ),
-            attach_other_files=[a for a in [
-                event.settings.get('mail_attachment_new_order', as_type=str, default='')[len('file://'):]
-            ] if a],
-        )
-    except SendMailException:
-        logger.exception('Order received email could not be sent to attendee')
+    position.send_mail(
+        subject_template, email_template, email_context,
+        log_entry,
+        invoices=[],
+        attach_tickets=True,
+        attach_ical=event.settings.mail_attach_ical and (
+            not event.settings.mail_attach_ical_paid_only or
+            is_free or
+            order.valid_if_pending
+        ),
+        attach_other_files=[a for a in [
+            event.settings.get('mail_attachment_new_order', as_type=str, default='')[len('file://'):]
+        ] if a],
+    )
 
 
 def _perform_order(event: Event, payment_requests: List[dict], position_ids: List[str],
@@ -1460,13 +1441,10 @@ def send_expiry_warnings(sender, **kwargs):
                         email_template = settings.mail_text_order_pending_warning
                         email_subject = settings.mail_subject_order_pending_warning
 
-                    try:
-                        o.send_mail(
-                            email_subject, email_template, email_context,
-                            'pretix.event.order.email.expire_warning_sent'
-                        )
-                    except SendMailException:
-                        logger.exception('Reminder email could not be sent')
+                    o.send_mail(
+                        email_subject, email_template, email_context,
+                        'pretix.event.order.email.expire_warning_sent'
+                    )
 
 
 @receiver(signal=periodic_task)
@@ -1527,14 +1505,11 @@ def send_download_reminders(sender, **kwargs):
                 email_template = event.settings.mail_text_download_reminder
                 email_subject = event.settings.mail_subject_download_reminder
                 email_context = get_email_context(event=event, order=o)
-                try:
-                    o.send_mail(
-                        email_subject, email_template, email_context,
-                        'pretix.event.order.email.download_reminder_sent',
-                        attach_tickets=True
-                    )
-                except SendMailException:
-                    logger.exception('Reminder email could not be sent')
+                o.send_mail(
+                    email_subject, email_template, email_context,
+                    'pretix.event.order.email.download_reminder_sent',
+                    attach_tickets=True
+                )
 
                 if event.settings.mail_send_download_reminder_attendee:
                     for p in positions:
@@ -1548,14 +1523,11 @@ def send_download_reminders(sender, **kwargs):
                             email_template = event.settings.mail_text_download_reminder_attendee
                             email_subject = event.settings.mail_subject_download_reminder_attendee
                             email_context = get_email_context(event=event, order=o, position=p)
-                            try:
-                                o.send_mail(
-                                    email_subject, email_template, email_context,
-                                    'pretix.event.order.email.download_reminder_sent',
-                                    attach_tickets=True, position=p
-                                )
-                            except SendMailException:
-                                logger.exception('Reminder email could not be sent to attendee')
+                            o.send_mail(
+                                email_subject, email_template, email_context,
+                                'pretix.event.order.email.download_reminder_sent',
+                                attach_tickets=True, position=p
+                            )
 
 
 def notify_user_changed_order(order, user=None, auth=None, invoices=[]):
@@ -1563,13 +1535,10 @@ def notify_user_changed_order(order, user=None, auth=None, invoices=[]):
         email_template = order.event.settings.mail_text_order_changed
         email_context = get_email_context(event=order.event, order=order)
         email_subject = order.event.settings.mail_subject_order_changed
-        try:
-            order.send_mail(
-                email_subject, email_template, email_context,
-                'pretix.event.order.email.order_changed', user, auth=auth, invoices=invoices, attach_tickets=True,
-            )
-        except SendMailException:
-            logger.exception('Order changed email could not be sent')
+        order.send_mail(
+            email_subject, email_template, email_context,
+            'pretix.event.order.email.order_changed', user, auth=auth, invoices=invoices, attach_tickets=True,
+        )
 
 
 class OrderChangeManager:

src/pretix/base/services/shredder.py

@@ -48,7 +48,7 @@ from django.utils.translation import gettext_lazy as _
 
 from pretix.base.i18n import language
 from pretix.base.models import CachedFile, Event, User, cachedfile_name
-from pretix.base.services.mail import SendMailException, mail
+from pretix.base.services.mail import mail
 from pretix.base.services.tasks import ProfiledEventTask
 from pretix.base.shredder import ShredError
 from pretix.celery_app import app
@@ -171,21 +171,18 @@ def shred(self, event: Event, fileid: str, confirm_code: str, user: int=None, lo
 
     if user:
         with language(user.locale):
-            try:
-                mail(
-                    user.email,
-                    _('Data shredding completed'),
-                    'pretixbase/email/shred_completed.txt',
-                    {
-                        'user': user,
-                        'organizer': event.organizer.name,
-                        'event': str(event.name),
-                        'start_time': date_format(parse(indexdata['time']).astimezone(event.timezone), 'SHORT_DATETIME_FORMAT'),
-                        'shredders': ', '.join([str(s.verbose_name) for s in shredders])
-                    },
-                    event=None,
-                    user=user,
-                    locale=user.locale,
-                )
-            except SendMailException:
-                pass  # Already logged
+            mail(
+                user.email,
+                _('Data shredding completed'),
+                'pretixbase/email/shred_completed.txt',
+                {
+                    'user': user,
+                    'organizer': event.organizer.name,
+                    'event': str(event.name),
+                    'start_time': date_format(parse(indexdata['time']).astimezone(event.timezone), 'SHORT_DATETIME_FORMAT'),
+                    'shredders': ', '.join([str(s.verbose_name) for s in shredders])
+                },
+                event=None,
+                user=user,
+                locale=user.locale,
+            )

src/pretix/control/views/auth.py

@@ -65,7 +65,6 @@ from pretix.base.forms.auth import (
 )
 from pretix.base.metrics import pretix_failed_logins, pretix_successful_logins
 from pretix.base.models import TeamInvite, U2FDevice, User, WebAuthnDevice
-from pretix.base.services.mail import SendMailException
 from pretix.helpers.http import get_client_ip, redirect_to_url
 from pretix.helpers.security import handle_login_source
 
@@ -342,9 +341,6 @@ class Forgot(TemplateView):
             except User.DoesNotExist:
                 logger.warning('Backend password reset for unregistered e-mail \"' + email + '\" requested.')
 
-            except SendMailException:
-                logger.exception('Sending password reset email to \"' + email + '\" failed.')
-
             except RepeatedResetDenied:
                 pass
 

src/pretix/control/views/orders.py

@@ -96,9 +96,7 @@ from pretix.base.services.invoices import (
     invoice_qualified, regenerate_invoice, transmit_invoice,
 )
 from pretix.base.services.locking import LockTimeoutException
-from pretix.base.services.mail import (
-    SendMailException, prefix_subject, render_mail,
-)
+from pretix.base.services.mail import prefix_subject, render_mail
 from pretix.base.services.orders import (
     OrderChangeManager, OrderError, approve_order, cancel_order, deny_order,
     extend_order, mark_order_expired, mark_order_refunded,
@@ -1054,10 +1052,6 @@ class OrderPaymentConfirm(OrderView):
                 messages.error(self.request, str(e))
             except PaymentException as e:
                 messages.error(self.request, str(e))
-            except SendMailException:
-                messages.warning(self.request,
-                                 _('The payment has been marked as complete, but we were unable to send a '
-                                   'confirmation mail.'))
             else:
                 messages.success(self.request, _('The payment has been marked as complete.'))
         else:
@@ -1527,9 +1521,6 @@ class OrderTransition(OrderView):
                     'message': str(e)
                 })
                 messages.error(self.request, str(e))
-            except SendMailException:
-                messages.warning(self.request, _('The order has been marked as paid, but we were unable to send a '
-                                                 'confirmation mail.'))
             else:
                 messages.success(self.request, _('The payment has been created successfully.'))
         elif self.order.cancel_allowed() and to == 'c':
@@ -1748,15 +1739,11 @@ class OrderResendLink(OrderView):
     permission = 'can_change_orders'
 
     def post(self, *args, **kwargs):
-        try:
-            if 'position' in kwargs:
-                p = get_object_or_404(self.order.positions, pk=kwargs['position'])
-                p.resend_link(user=self.request.user)
-            else:
-                self.order.resend_link(user=self.request.user)
-        except SendMailException:
-            messages.error(self.request, _('There was an error sending the mail. Please try again later.'))
-            return redirect(self.get_order_url())
+        if 'position' in kwargs:
+            p = get_object_or_404(self.order.positions, pk=kwargs['position'])
+            p.resend_link(user=self.request.user)
+        else:
+            self.order.resend_link(user=self.request.user)
 
         messages.success(self.request, _('The email has been queued to be sent.'))
         return redirect(self.get_order_url())
@@ -2399,24 +2386,18 @@ class OrderSendMail(EventPermissionRequiredMixin, OrderViewMixin, FormView):
             }
             return self.get(self.request, *self.args, **self.kwargs)
         else:
-            try:
-                order.send_mail(
-                    form.cleaned_data['subject'], email_template,
-                    email_context, 'pretix.event.order.email.custom_sent',
-                    self.request.user, auto_email=False,
-                    attach_tickets=form.cleaned_data.get('attach_tickets', False),
-                    invoices=form.cleaned_data.get('attach_invoices', []),
-                    attach_other_files=[a for a in [
-                        self.request.event.settings.get('mail_attachment_new_order', as_type=str, default='')[len('file://'):]
-                    ] if a] if form.cleaned_data.get('attach_new_order', False) else [],
-                )
-                messages.success(self.request,
-                                 _('Your message has been queued and will be sent to {}.'.format(order.email)))
-            except SendMailException:
-                messages.error(
-                    self.request,
-                    _('Failed to send mail to the following user: {}'.format(order.email))
-                )
+            order.send_mail(
+                form.cleaned_data['subject'], email_template,
+                email_context, 'pretix.event.order.email.custom_sent',
+                self.request.user, auto_email=False,
+                attach_tickets=form.cleaned_data.get('attach_tickets', False),
+                invoices=form.cleaned_data.get('attach_invoices', []),
+                attach_other_files=[a for a in [
+                    self.request.event.settings.get('mail_attachment_new_order', as_type=str, default='')[len('file://'):]
+                ] if a] if form.cleaned_data.get('attach_new_order', False) else [],
+            )
+            messages.success(self.request,
+                             _('Your message has been queued and will be sent to {}.'.format(order.email)))
             return super(OrderSendMail, self).form_valid(form)
 
     def get_success_url(self):
@@ -2469,23 +2450,19 @@ class OrderPositionSendMail(OrderSendMail):
             }
             return self.get(self.request, *self.args, **self.kwargs)
         else:
-            try:
-                position.send_mail(
-                    form.cleaned_data['subject'],
-                    email_template,
-                    email_context,
-                    'pretix.event.order.position.email.custom_sent',
-                    self.request.user,
-                    attach_tickets=form.cleaned_data.get('attach_tickets', False),
-                    attach_other_files=[a for a in [
-                        self.request.event.settings.get('mail_attachment_new_order', as_type=str, default='')[len('file://'):]
-                    ] if a] if form.cleaned_data.get('attach_new_order', False) else [],
-                )
-                messages.success(self.request,
-                                 _('Your message has been queued and will be sent to {}.'.format(position.attendee_email)))
-            except SendMailException:
-                messages.error(self.request,
-                               _('Failed to send mail to the following user: {}'.format(position.attendee_email)))
+            position.send_mail(
+                form.cleaned_data['subject'],
+                email_template,
+                email_context,
+                'pretix.event.order.position.email.custom_sent',
+                self.request.user,
+                attach_tickets=form.cleaned_data.get('attach_tickets', False),
+                attach_other_files=[a for a in [
+                    self.request.event.settings.get('mail_attachment_new_order', as_type=str, default='')[len('file://'):]
+                ] if a] if form.cleaned_data.get('attach_new_order', False) else [],
+            )
+            messages.success(self.request,
+                             _('Your message has been queued and will be sent to {}.'.format(position.attendee_email)))
             return super(OrderSendMail, self).form_valid(form)
 
 

src/pretix/control/views/organizer.py

@@ -102,7 +102,7 @@ from pretix.base.plugins import (
     PLUGIN_LEVEL_ORGANIZER,
 )
 from pretix.base.services.export import multiexport, scheduled_organizer_export
-from pretix.base.services.mail import SendMailException, mail, prefix_subject
+from pretix.base.services.mail import mail, prefix_subject
 from pretix.base.signals import register_multievent_data_exporters
 from pretix.base.templatetags.rich_text import markdown_compile_email
 from pretix.base.views.tasks import AsyncAction
@@ -1036,24 +1036,21 @@ class TeamMemberView(OrganizerDetailViewMixin, OrganizerPermissionRequiredMixin,
         return ctx
 
     def _send_invite(self, instance):
-        try:
-            mail(
-                instance.email,
-                _('pretix account invitation'),
-                'pretixcontrol/email/invitation.txt',
-                {
-                    'user': self,
-                    'organizer': self.request.organizer.name,
-                    'team': instance.team.name,
-                    'url': build_global_uri('control:auth.invite', kwargs={
-                        'token': instance.token
-                    })
-                },
-                event=None,
-                locale=self.request.LANGUAGE_CODE
-            )
-        except SendMailException:
-            pass  # Already logged
+        mail(
+            instance.email,
+            _('pretix account invitation'),
+            'pretixcontrol/email/invitation.txt',
+            {
+                'user': self,
+                'organizer': self.request.organizer.name,
+                'team': instance.team.name,
+                'url': build_global_uri('control:auth.invite', kwargs={
+                    'token': instance.token
+                })
+            },
+            event=None,
+            locale=self.request.LANGUAGE_CODE
+        )
 
     @transaction.atomic
     def post(self, request, *args, **kwargs):

src/pretix/control/views/users.py

@@ -41,7 +41,6 @@ from hijack import signals
 
 from pretix.base.auth import get_auth_backends
 from pretix.base.models import User
-from pretix.base.services.mail import SendMailException
 from pretix.control.forms.filter import UserFilterForm
 from pretix.control.forms.users import UserEditForm
 from pretix.control.permissions import AdministratorPermissionRequiredMixin
@@ -139,11 +138,7 @@ class UserResetView(AdministratorPermissionRequiredMixin, RecentAuthenticationRe
 
     def post(self, request, *args, **kwargs):
         self.object = get_object_or_404(User, pk=self.kwargs.get("id"))
-        try:
-            self.object.send_password_reset()
-        except SendMailException:
-            messages.error(request, _('There was an error sending the mail. Please try again later.'))
-            return redirect(self.get_success_url())
+        self.object.send_password_reset()
 
         self.object.log_action('pretix.control.auth.user.forgot_password.mail_sent',
                                user=request.user)

src/pretix/helpers/security.py

@@ -32,7 +32,7 @@ from django_countries.fields import Country
 from geoip2.errors import AddressNotFoundError
 
 from pretix.base.i18n import language
-from pretix.base.services.mail import SendMailException, mail
+from pretix.base.services.mail import mail
 from pretix.helpers.http import get_client_ip
 from pretix.helpers.urls import build_absolute_uri
 
@@ -159,21 +159,18 @@ def handle_login_source(user, request):
         })
         if user.known_login_sources.count() > 1:
             # Do not send on first login or first login after introduction of this feature:
-            try:
-                with language(user.locale):
-                    mail(
-                        user.email,
-                        _('Login from new source detected'),
-                        'pretixcontrol/email/login_notice.txt',
-                        {
-                            'source': src,
-                            'country': Country(str(country)).name if country else _('Unknown country'),
-                            'instance': settings.PRETIX_INSTANCE_NAME,
-                            'url': build_absolute_uri('control:user.settings')
-                        },
-                        event=None,
-                        user=user,
-                        locale=user.locale
-                    )
-            except SendMailException:
-                pass  # Not much we can do
+            with language(user.locale):
+                mail(
+                    user.email,
+                    _('Login from new source detected'),
+                    'pretixcontrol/email/login_notice.txt',
+                    {
+                        'source': src,
+                        'country': Country(str(country)).name if country else _('Unknown country'),
+                        'instance': settings.PRETIX_INSTANCE_NAME,
+                        'url': build_absolute_uri('control:user.settings')
+                    },
+                    event=None,
+                    user=user,
+                    locale=user.locale
+                )

src/pretix/plugins/banktransfer/tasks.py

@@ -54,7 +54,6 @@ from pretix.base.models import (
 )
 from pretix.base.payment import PaymentException
 from pretix.base.services.locking import LockTimeoutException
-from pretix.base.services.mail import SendMailException
 from pretix.base.services.orders import change_payment_provider
 from pretix.base.services.tasks import TransactionAwareTask
 from pretix.celery_app import app
@@ -70,13 +69,10 @@ def notify_incomplete_payment(o: Order):
         email_context = get_email_context(event=o.event, order=o, pending_sum=o.pending_sum)
         email_subject = o.event.settings.mail_subject_order_incomplete_payment
 
-        try:
-            o.send_mail(
-                email_subject, email_template, email_context,
-                'pretix.event.order.email.expire_warning_sent'
-            )
-        except SendMailException:
-            logger.exception('Reminder email could not be sent')
+        o.send_mail(
+            email_subject, email_template, email_context,
+            'pretix.event.order.email.expire_warning_sent'
+        )
 
 
 def cancel_old_payments(order):
@@ -279,9 +275,6 @@ def _handle_transaction(trans: BankTransaction, matches: tuple, event: Event = N
         except Quota.QuotaExceededException:
             # payment confirmed but order status could not be set, no longer problem of this plugin
             cancel_old_payments(order)
-        except SendMailException:
-            # payment confirmed but order status could not be set, no longer problem of this plugin
-            cancel_old_payments(order)
         else:
             cancel_old_payments(order)
 

src/pretix/plugins/banktransfer/views.py

@@ -58,7 +58,6 @@ from localflavor.generic.forms import BICFormField, IBANFormField
 
 from pretix.base.forms.widgets import DatePickerWidget
 from pretix.base.models import Event, Order, OrderPayment, OrderRefund, Quota
-from pretix.base.services.mail import SendMailException
 from pretix.base.settings import SettingsSandbox
 from pretix.base.templatetags.money import money_filter
 from pretix.control.permissions import (
@@ -160,11 +159,6 @@ class ActionView(View):
             p.confirm(user=self.request.user)
         except Quota.QuotaExceededException:
             pass
-        except SendMailException:
-            return JsonResponse({
-                'status': 'error',
-                'message': _('Problem sending email.')
-            })
         trans.state = BankTransaction.STATE_VALID
         trans.save()
         trans.order.payments.filter(

src/pretix/plugins/paypal/payment.py

@@ -57,7 +57,6 @@ from pretix.base.decimal import round_decimal
 from pretix.base.forms import SecretKeySettingsField
 from pretix.base.models import Event, Order, OrderPayment, OrderRefund, Quota
 from pretix.base.payment import BasePaymentProvider, PaymentException
-from pretix.base.services.mail import SendMailException
 from pretix.base.settings import SettingsSandbox
 from pretix.multidomain.urlreverse import build_absolute_uri
 from pretix.plugins.paypal.api import Api
@@ -468,9 +467,6 @@ class Paypal(BasePaymentProvider):
             payment_obj.confirm()
         except Quota.QuotaExceededException as e:
             raise PaymentException(str(e))
-
-        except SendMailException:
-            messages.warning(request, _('There was an error sending the confirmation mail.'))
         return None
 
     def payment_pending_render(self, request, payment) -> str:

src/pretix/plugins/paypal2/payment.py

@@ -54,7 +54,6 @@ from pretix.base.forms import SecretKeySettingsField
 from pretix.base.forms.questions import guess_country
 from pretix.base.models import Event, Order, OrderPayment, OrderRefund, Quota
 from pretix.base.payment import BasePaymentProvider, PaymentException
-from pretix.base.services.mail import SendMailException
 from pretix.base.settings import SettingsSandbox
 from pretix.helpers import OF_SELF
 from pretix.helpers.urls import build_absolute_uri as build_global_uri
@@ -821,9 +820,6 @@ class PaypalMethod(BasePaymentProvider):
                 payment.confirm()
             except Quota.QuotaExceededException as e:
                 raise PaymentException(str(e))
-
-            except SendMailException:
-                messages.warning(request, _('There was an error sending the confirmation mail.'))
         finally:
             if 'payment_paypal_oid' in request.session:
                 del request.session['payment_paypal_oid']

src/pretix/plugins/sendmail/models.py

@@ -38,7 +38,6 @@ from pretix.base.models import (
     fields,
 )
 from pretix.base.models.base import LoggingMixin
-from pretix.base.services.mail import SendMailException
 
 
 class ScheduledMail(models.Model):
@@ -180,13 +179,10 @@ class ScheduledMail(models.Model):
                         invoice_address=ia,
                         event_or_subevent=self.subevent or e,
                     )
-                    try:
-                        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
-                    except SendMailException:
-                        ...  # ¯\_(ツ)_/¯
+                    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:
@@ -195,31 +191,28 @@ class ScheduledMail(models.Model):
                         positions = [p for p in positions if p.subevent_id == self.subevent_id]
 
                     for p in positions:
-                        try:
-                            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
-                        except SendMailException:
-                            ...  # ¯\_(ツ)_/¯
+                        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

@@ -41,7 +41,7 @@ from pretix.base.i18n import language
 from pretix.base.models import (
     CachedFile, Checkin, Event, InvoiceAddress, Order, User,
 )
-from pretix.base.services.mail import SendMailException, mail
+from pretix.base.services.mail import mail
 from pretix.base.services.tasks import ProfiledEventTask
 from pretix.celery_app import app
 from pretix.helpers.format import format_map
@@ -53,7 +53,6 @@ def send_mails_to_orders(event: Event, user: int, subject: dict, message: dict,
                          recipients: str, filter_checkins: bool, not_checked_in: bool, checkin_lists: list,
                          attachments: list = None, attach_tickets: bool = False,
                          attach_ical: bool = False) -> None:
-    failures = []
     user = User.objects.get(pk=user) if user else None
     orders = Order.objects.filter(pk__in=objects, event=event)
     subject = LazyI18nString(subject)
@@ -114,70 +113,64 @@ def send_mails_to_orders(event: Event, user: int, subject: dict, message: dict,
                 if subevents_to and p.subevent.date_from >= subevents_to:
                     continue
 
-                try:
-                    with language(o.locale, event.settings.region):
-                        email_context = get_email_context(event=event, order=o, invoice_address=ia, position=p)
-                        mail(
-                            p.attendee_email,
-                            subject,
-                            message,
-                            email_context,
-                            event,
-                            locale=o.locale,
-                            order=o,
-                            position=p,
-                            attach_tickets=attach_tickets,
-                            attach_ical=attach_ical,
-                            attach_cached_files=attachments
-                        )
-                        o.log_action(
-                            'pretix.plugins.sendmail.order.email.sent.attendee',
-                            user=user,
-                            data={
-                                'position': p.positionid,
-                                'subject': format_map(subject.localize(o.locale), email_context),
-                                'message': format_map(message.localize(o.locale), email_context),
-                                'recipient': p.attendee_email,
-                                'attach_tickets': attach_tickets,
-                                'attach_ical': attach_ical,
-                                'attach_other_files': [],
-                                'attach_cached_files': attachments_for_log,
-                            }
-                        )
-                except SendMailException:
-                    failures.append(p.attendee_email)
-
-        if send_to_order and o.email:
-            try:
                 with language(o.locale, event.settings.region):
-                    email_context = get_email_context(event=event, order=o, invoice_address=ia)
+                    email_context = get_email_context(event=event, order=o, invoice_address=ia, position=p)
                     mail(
-                        o.email,
+                        p.attendee_email,
                         subject,
                         message,
                         email_context,
                         event,
                         locale=o.locale,
                         order=o,
+                        position=p,
                         attach_tickets=attach_tickets,
                         attach_ical=attach_ical,
-                        attach_cached_files=attachments,
+                        attach_cached_files=attachments
                     )
                     o.log_action(
-                        'pretix.plugins.sendmail.order.email.sent',
+                        'pretix.plugins.sendmail.order.email.sent.attendee',
                         user=user,
                         data={
+                            'position': p.positionid,
                             'subject': format_map(subject.localize(o.locale), email_context),
                             'message': format_map(message.localize(o.locale), email_context),
-                            'recipient': o.email,
+                            'recipient': p.attendee_email,
                             'attach_tickets': attach_tickets,
                             'attach_ical': attach_ical,
                             'attach_other_files': [],
                             'attach_cached_files': attachments_for_log,
                         }
                     )
-            except SendMailException:
-                failures.append(o.email)
+
+        if send_to_order and o.email:
+            with language(o.locale, event.settings.region):
+                email_context = get_email_context(event=event, order=o, invoice_address=ia)
+                mail(
+                    o.email,
+                    subject,
+                    message,
+                    email_context,
+                    event,
+                    locale=o.locale,
+                    order=o,
+                    attach_tickets=attach_tickets,
+                    attach_ical=attach_ical,
+                    attach_cached_files=attachments,
+                )
+                o.log_action(
+                    'pretix.plugins.sendmail.order.email.sent',
+                    user=user,
+                    data={
+                        'subject': format_map(subject.localize(o.locale), email_context),
+                        'message': format_map(message.localize(o.locale), email_context),
+                        'recipient': o.email,
+                        'attach_tickets': attach_tickets,
+                        'attach_ical': attach_ical,
+                        'attach_other_files': [],
+                        'attach_cached_files': attachments_for_log,
+                    }
+                )
 
 
 @app.task(base=ProfiledEventTask, acks_late=True)

src/pretix/plugins/stripe/payment.py

@@ -71,7 +71,6 @@ from pretix.base.payment import (
     BasePaymentProvider, PaymentException, WalletQueries,
 )
 from pretix.base.plugins import get_all_plugins
-from pretix.base.services.mail import SendMailException
 from pretix.base.settings import SettingsSandbox
 from pretix.helpers import OF_SELF
 from pretix.helpers.countries import CachedCountries
@@ -980,9 +979,6 @@ class StripeMethod(BasePaymentProvider):
                     payment.confirm()
                 except Quota.QuotaExceededException as e:
                     raise PaymentException(str(e))
-
-                except SendMailException:
-                    raise PaymentException(_('There was an error sending the confirmation mail.'))
             elif intent.status == 'processing':
                 if request:
                     messages.warning(request, _('Your payment is pending completion. We will inform you as soon as the '

src/pretix/presale/checkoutflow.py

@@ -1643,11 +1643,6 @@ class ConfirmStep(CartMixin, AsyncAction, TemplateFlowStep):
         order = Order.objects.get(id=value)
         return self.get_order_url(order)
 
-    def get_error_message(self, exception):
-        if exception.__class__.__name__ == 'SendMailException':
-            return _('There was an error sending the confirmation mail. Please try again later.')
-        return super().get_error_message(exception)
-
     def get_error_url(self):
         return self.get_step_url(self.request)
 

src/pretix/presale/views/order.py

@@ -75,7 +75,6 @@ from pretix.base.services.invoices import (
     generate_cancellation, generate_invoice, invoice_pdf, invoice_pdf_task,
     invoice_qualified,
 )
-from pretix.base.services.mail import SendMailException
 from pretix.base.services.orders import (
     OrderChangeManager, OrderError, _try_auto_refund, cancel_order,
     change_payment_provider, error_messages,
@@ -595,10 +594,7 @@ class OrderPayChangeMethod(EventViewMixin, OrderDetailMixin, TemplateView):
                 amount=Decimal('0.00'),
                 fee=None
             )
-            try:
-                p.confirm()
-            except SendMailException:
-                pass
+            p.confirm()
         else:
             p._mark_order_paid(
                 payment_refund_sum=self.order.payment_refund_sum

src/pretix/presale/views/user.py

@@ -32,8 +32,6 @@
 # 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 django.conf import settings
 from django.contrib import messages
 from django.utils.functional import cached_property
@@ -42,7 +40,7 @@ from django.views import View
 from django.views.generic import TemplateView
 
 from pretix.base.email import get_email_context
-from pretix.base.services.mail import INVALID_ADDRESS, SendMailException, mail
+from pretix.base.services.mail import INVALID_ADDRESS, mail
 from pretix.helpers.http import redirect_to_url
 from pretix.multidomain.urlreverse import eventreverse
 from pretix.presale.forms.user import ResendLinkForm
@@ -83,13 +81,7 @@ class ResendLinkView(EventViewMixin, TemplateView):
         subject = self.request.event.settings.mail_subject_resend_all_links
         template = self.request.event.settings.mail_text_resend_all_links
         context = get_email_context(event=self.request.event, orders=orders)
-        try:
-            mail(user, subject, template, context, event=self.request.event, locale=self.request.LANGUAGE_CODE)
-        except SendMailException:
-            logger = logging.getLogger('pretix.presale.user')
-            logger.exception('A mail resending order links to {} could not be sent.'.format(user))
-            messages.error(self.request, _('We have trouble sending emails right now, please check back later.'))
-            return self.get(request, *args, **kwargs)
+        mail(user, subject, template, context, event=self.request.event, locale=self.request.LANGUAGE_CODE)
 
         messages.success(self.request, _('If there were any orders by this user, they will receive an email with their order codes.'))
         return redirect_to_url(eventreverse(self.request.event, 'presale:event.index'))

src/pretix/testutils/mail.py

@@ -0,0 +1,10 @@
+import smtplib
+
+from django.core.mail.backends.locmem import EmailBackend
+
+
+class FailingEmailBackend(EmailBackend):
+    def send_messages(self, email_messages):
+        raise smtplib.SMTPRecipientsRefused({
+            'recipient@example.org': (450, b'Recipient unknown')
+        })