diff --git a/src/pretix/base/migrations/0297_outgoingmail.py b/src/pretix/base/migrations/0297_outgoingmail.py
index edc5f36565..6f52877391 100644
--- a/src/pretix/base/migrations/0297_outgoingmail.py
+++ b/src/pretix/base/migrations/0297_outgoingmail.py
@@ -1,4 +1,5 @@
 # Generated by Django 4.2.26 on 2026-01-22 13:44
+import uuid
 
 import django.db.models.deletion
 from django.conf import settings
@@ -23,6 +24,7 @@ class Migration(migrations.Migration):
                         auto_created=True, primary_key=True, serialize=False
                     ),
                 ),
+                ("guid", models.UUIDField(db_index=True, default=uuid.uuid4)),
                 ("status", models.CharField(default="queued", max_length=200)),
                 ("created", models.DateTimeField(auto_now_add=True)),
                 ("sent", models.DateTimeField(blank=True, null=True)),
diff --git a/src/pretix/base/models/mail.py b/src/pretix/base/models/mail.py
index 50cd15d2cf..257125d165 100644
--- a/src/pretix/base/models/mail.py
+++ b/src/pretix/base/models/mail.py
@@ -19,6 +19,8 @@
 # You should have received a copy of the GNU Affero General Public License along with this program.  If not, see
 # <https://www.gnu.org/licenses/>.
 #
+import uuid
+
 from django.core.mail import get_connection
 from django.db import models
 from django.utils.translation import gettext_lazy as _
@@ -44,14 +46,17 @@ class OutgoingMail(models.Model):
     STATUS_AWAWITING_RETRY = "awaiting_retry"
     STATUS_FAILED = "failed"
     STATUS_SENT = "sent"
+    STATUS_BOUNCED = "bounced"
     STATUS_CHOICES = (
         (STATUS_QUEUED, _("queued")),
         (STATUS_INFLIGHT, _("being sent")),
         (STATUS_AWAWITING_RETRY, _("awaiting retry")),
         (STATUS_FAILED, _("failed")),
         (STATUS_SENT, _("sent")),
+        (STATUS_BOUNCED, _("bounced")),
     )
 
+    guid = models.UUIDField(db_index=True, default=uuid.uuid4)
     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)
@@ -157,6 +162,10 @@ class OutgoingMail(models.Model):
         else:
             return scopes_disabled()  # noqa
 
+    @property
+    def is_failed(self):
+        return self.status in (OutgoingMail.STATUS_FAILED, OutgoingMail.STATUS_AWAWITING_RETRY, OutgoingMail.STATUS_BOUNCED)
+
     def save(self, *args, **kwargs):
         if self.orderposition_id and not self.order_id:
             self.order = self.orderposition.order
diff --git a/src/pretix/base/services/mail.py b/src/pretix/base/services/mail.py
index d0b9352b2f..498adcfb7b 100644
--- a/src/pretix/base/services/mail.py
+++ b/src/pretix/base/services/mail.py
@@ -39,6 +39,7 @@ import mimetypes
 import os
 import re
 import smtplib
+import uuid
 import warnings
 from datetime import timedelta
 from email.mime.image import MIMEImage
@@ -213,10 +214,12 @@ def mail(email: Union[str, Sequence[str]], subject: str, template: Union[str, La
     settings_holder = event or organizer
 
     headers = headers or {}
+    guid = uuid.uuid4()
     if auto_email:
         headers['X-Auto-Response-Suppress'] = 'OOF, NRN, AutoReply, RN'
         headers['Auto-Submitted'] = 'auto-generated'
     headers.setdefault('X-Mailer', 'pretix')
+    headers.setdefault('X-PX-Correlation', str(guid))
 
     bcc = list(bcc or [])
     if settings_holder and settings_holder.settings.mail_bcc:
@@ -301,9 +304,9 @@ def mail(email: Union[str, Sequence[str]], subject: str, template: Union[str, La
             orderposition=position,
             customer=customer,
             user=user,
-            to=[email] if isinstance(email, str) else list(email),
-            cc=cc or [],
-            bcc=bcc or [],
+            to=[email.lower()] if isinstance(email, str) else [e.lower() for e in email],
+            cc=[e.lower() for e in cc] if cc else [],
+            bcc=[e.lower() for e in bcc] if bcc else [],
             subject=subject,
             body_plain=body_plain,
             body_html=body_html,
@@ -395,7 +398,6 @@ def mail_send_task(self, *args, outgoing_mail: int) -> bool:
 
     log_target, error_log_action_type = outgoing_mail.log_parameters()
     invoices_attached = []
-    actual_attachments = []
 
     with outgoing_mail.scope_manager():
         # Attach tickets
@@ -566,21 +568,21 @@ def mail_send_task(self, *args, outgoing_mail: int) -> bool:
 
                     outgoing_mail.status = OutgoingMail.STATUS_AWAWITING_RETRY
                     outgoing_mail.retry_after = now() + timedelta(seconds=retry_after)
-                    outgoing_mail.save(update_fields=["status", "error", "error_detail", "sent", "retry_after"])
+                    outgoing_mail.save(update_fields=["status", "error", "error_detail", "sent", "retry_after", "actual_attachments"])
                     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.retry_after = now() + timedelta(seconds=retry_after)
-                    outgoing_mail.save(update_fields=["status", "error", "error_detail", "sent", "retry_after"])
+                    outgoing_mail.save(update_fields=["status", "error", "error_detail", "sent", "retry_after", "actual_attachments"])
                     self.retry(max_retries=max_retries, countdown=retry_after)  # throws RetryException, ends function flow
 
                 elif retry_strategy == "slow":
                     retry_after = [60, 300, 600, 1200, 1800, 1800][self.request.retries]
                     outgoing_mail.status = OutgoingMail.STATUS_AWAWITING_RETRY
                     outgoing_mail.retry_after = now() + timedelta(seconds=retry_after)
-                    outgoing_mail.save(update_fields=["status", "error", "error_detail", "sent", "retry_after"])
+                    outgoing_mail.save(update_fields=["status", "error", "error_detail", "sent", "retry_after", "actual_attachments"])
                     self.retry(max_retries=5, countdown=retry_after)  # throws RetryException, ends function flow
 
             except MaxRetriesExceededError:
@@ -605,14 +607,14 @@ def mail_send_task(self, *args, outgoing_mail: int) -> bool:
                 outgoing_mail.status = OutgoingMail.STATUS_FAILED
                 outgoing_mail.sent = now()
                 outgoing_mail.retry_after = None
-                outgoing_mail.save(update_fields=["status", "error", "error_detail", "sent", "retry_after"])
+                outgoing_mail.save(update_fields=["status", "error", "error_detail", "sent", "retry_after", "actual_attachments"])
                 return False
 
             # If we reach this, it's a non-retryable error
             outgoing_mail.status = OutgoingMail.STATUS_FAILED
             outgoing_mail.sent = now()
             outgoing_mail.retry_after = None
-            outgoing_mail.save(update_fields=["status", "error", "error_detail", "sent", "retry_after"])
+            outgoing_mail.save(update_fields=["status", "error", "error_detail", "sent", "retry_after", "actual_attachments"])
             for i in invoices_to_mark_transmitted:
                 i.set_transmission_failed(provider="email_pdf", data={
                     "reason": "exception",
@@ -634,7 +636,6 @@ def mail_send_task(self, *args, outgoing_mail: int) -> bool:
             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.retry_after = None
             outgoing_mail.save(update_fields=["status", "error", "error_detail", "sent", "actual_attachments", "retry_after"])
@@ -974,8 +975,13 @@ def retry_stuck_queued_mails(sender, **kwargs):
         return
 
     for m in OutgoingMail.objects.filter(
-        status=OutgoingMail.STATUS_QUEUED,
-        created__lt=now() - timedelta(hours=1),
+        Q(
+            status=OutgoingMail.STATUS_QUEUED,
+            created__lt=now() - timedelta(hours=1),
+        ) | Q(
+            status=OutgoingMail.STATUS_AWAWITING_RETRY,
+            retry_after__lt=now() - timedelta(hours=1),
+        )
     ):
         mail_send_task.apply_async(kwargs={"outgoing_mail": m.pk})
 
diff --git a/src/pretix/base/services/notifications.py b/src/pretix/base/services/notifications.py
index b63eefaeca..0a70e7c32d 100644
--- a/src/pretix/base/services/notifications.py
+++ b/src/pretix/base/services/notifications.py
@@ -19,6 +19,8 @@
 # You should have received a copy of the GNU Affero General Public License along with this program.  If not, see
 # <https://www.gnu.org/licenses/>.
 #
+import uuid
+
 import css_inline
 from django.conf import settings
 from django.template.loader import get_template
@@ -155,7 +157,9 @@ def send_notification_mail(notification: Notification, user: User):
     tpl_plain = get_template('pretixbase/email/notification.txt')
     body_plain = tpl_plain.render(ctx)
 
+    guid = uuid.uuid4()
     m = OutgoingMail.objects.create(
+        guid=guid,
         user=user,
         to=[user.email],
         subject='[{}] {}: {}'.format(
@@ -166,7 +170,12 @@ def send_notification_mail(notification: Notification, user: User):
         body_plain=body_plain,
         body_html=body_html,
         sender=settings.MAIL_FROM_NOTIFICATIONS,
-        headers={},
+        headers={
+            'X-Auto-Response-Suppress': 'OOF, NRN, AutoReply, RN',
+            'Auto-Submitted': 'auto-generated',
+            'X-Mailer': 'pretix',
+            'X-PX-Correlation': str(guid),
+        },
     )
     mail_send_task.apply_async(kwargs={
         'outgoing_mail': m.pk,
diff --git a/src/pretix/control/forms/filter.py b/src/pretix/control/forms/filter.py
index 0f3b2a1e44..258ce064ba 100644
--- a/src/pretix/control/forms/filter.py
+++ b/src/pretix/control/forms/filter.py
@@ -57,8 +57,9 @@ from pretix.base.forms.widgets import (
 from pretix.base.models import (
     Checkin, CheckinList, Device, Event, EventMetaProperty, EventMetaValue,
     Gate, Invoice, InvoiceAddress, Item, Order, OrderPayment, OrderPosition,
-    OrderRefund, Organizer, Question, QuestionAnswer, Quota, SalesChannel,
-    SubEvent, SubEventMetaValue, Team, TeamAPIToken, TeamInvite, Voucher,
+    OrderRefund, Organizer, OutgoingMail, Question, QuestionAnswer, Quota,
+    SalesChannel, SubEvent, SubEventMetaValue, Team, TeamAPIToken, TeamInvite,
+    Voucher,
 )
 from pretix.base.signals import register_payment_providers
 from pretix.base.timeframes import (
@@ -2815,3 +2816,61 @@ class DeviceFilterForm(FilterForm):
             qs = qs.order_by('-device_id')
 
         return qs
+
+
+class OutgoingMailFilterForm(FilterForm):
+    orders = {
+        'date': 'd',
+        '-date': '-d',
+    }
+    query = forms.CharField(
+        label=_('Search email address or subject'),
+        widget=forms.TextInput(attrs={
+            'placeholder': _('Search email address or subject'),
+        }),
+        required=False
+    )
+    event = forms.ModelChoiceField(
+        queryset=Event.objects.none(),
+        label=_('Event'),
+        empty_label=_('All events'),
+        required=False,
+    )
+    status = forms.ChoiceField(
+        label=_('Status'),
+        choices=[
+            ('', _('All')),
+            *OutgoingMail.STATUS_CHOICES,
+        ],
+        required=False
+    )
+
+    def __init__(self, *args, **kwargs):
+        request = kwargs.pop('request')
+        super().__init__(*args, **kwargs)
+        self.fields['event'].queryset = request.organizer.events.all()
+
+    def filter_qs(self, qs):
+        fdata = self.cleaned_data
+
+        if fdata.get('query'):
+            query = fdata.get('query')
+            qs = qs.filter(
+                Q(to__containsstring=query)
+                | Q(cc__containsstring=query)
+                | Q(bcc_containsstring=query)
+                | Q(subject__icontains=query)
+            )
+
+        if fdata.get('event'):
+            qs = qs.filter(event=fdata['event'])
+
+        if fdata.get('status'):
+            qs = qs.filter(status=fdata['status'])
+
+        if fdata.get('ordering'):
+            qs = qs.order_by(self.get_order_by())
+        else:
+            qs = qs.order_by("-created", "-pk")
+
+        return qs
diff --git a/src/pretix/control/logdisplay.py b/src/pretix/control/logdisplay.py
index 02ccce2e4c..c34cfa104a 100644
--- a/src/pretix/control/logdisplay.py
+++ b/src/pretix/control/logdisplay.py
@@ -699,6 +699,7 @@ class CoreUserImpersonatedLogEntryType(UserImpersonatedLogEntryType):
     'pretix.organizer.export.schedule.deleted': _('A scheduled export has been deleted.'),
     'pretix.organizer.export.schedule.executed': _('A scheduled export has been executed.'),
     'pretix.organizer.export.schedule.failed': _('A scheduled export has failed: {reason}.'),
+    'pretix.organizer.outgoingmails.retried': _('Failed emails have been scheduled to be retried.'),
     'pretix.giftcards.acceptance.added': _('Gift card acceptance for another organizer has been added.'),
     'pretix.giftcards.acceptance.removed': _('Gift card acceptance for another organizer has been removed.'),
     'pretix.giftcards.acceptance.acceptor.invited': _('A new gift card acceptor has been invited.'),
diff --git a/src/pretix/control/navigation.py b/src/pretix/control/navigation.py
index c3a0cbb8f9..a6e3209788 100644
--- a/src/pretix/control/navigation.py
+++ b/src/pretix/control/navigation.py
@@ -679,6 +679,15 @@ def get_organizer_navigation(request):
             'active': (url.url_name == 'organizer.datasync.failedjobs'),
         }])
 
+        nav.append({
+            'label': _('Outgoing emails'),
+            'url': reverse('control:organizer.outgoingmails', kwargs={
+                'organizer': request.organizer.slug,
+            }),
+            'active': 'organizer.outgoingmail' in url.url_name,
+            'icon': 'send',
+        })
+
     merge_in(nav, sorted(
         sum((list(a[1]) for a in nav_organizer.send(request.organizer, request=request, organizer=request.organizer)),
             []),
diff --git a/src/pretix/control/templates/pretixcontrol/organizers/outgoing_mail.html b/src/pretix/control/templates/pretixcontrol/organizers/outgoing_mail.html
new file mode 100644
index 0000000000..ae033f3043
--- /dev/null
+++ b/src/pretix/control/templates/pretixcontrol/organizers/outgoing_mail.html
@@ -0,0 +1,192 @@
+{% extends "pretixcontrol/organizers/base.html" %}
+{% load i18n %}
+{% load bootstrap3 %}
+{% load urlreplace %}
+{% load icon %}
+{% load compress %}
+{% load static %}
+{% block inner %}
+    <h1>
+        {% trans "Outgoing email" %}
+    </h1>
+    <div class="panel panel-default">
+        <div class="panel-heading">
+            <h3 class="panel-title">{% trans "Email details" %}</h3>
+        </div>
+        <div class="panel-body">
+            <div class="row">
+                <div class="col-lg-7 col-md-12">
+
+                    <dl class="dl-horizontal">
+                        <dt>{% trans "From" context "email" %}</dt>
+                        <dd>{{ mail.sender }}</dd>
+                        <dt>{% trans "To" context "email" %}</dt>
+                        <dd>{{ mail.to|join:", " }}</dd>
+                        {% if mail.cc %}
+                            <dt>{% trans "Cc" context "email" %}</dt>
+                            <dd>{{ mail.cc|join:", " }}</dd>
+                        {% endif %}
+                        {% if mail.bcc %}
+                            <dt>{% trans "Bcc" context "email" %}</dt>
+                            <dd>{{ mail.bcc|join:", " }}</dd>
+                        {% endif %}
+                        <dt>{% trans "Subject" %}</dt>
+                        <dd>{{ mail.subject }}</dd>
+                        <dt>{% trans "Status" %}</dt>
+                        <dd>
+                            {% if mail.status == "queued" %}
+                                <span class="label label-info">{% icon "clock" %} {% trans "queued" %}</span>
+                            {% elif mail.status == "inflight" %}
+                                <span class="label label-info">{% icon "send" %} {% trans "being sent" %}</span>
+                            {% elif mail.status == "awaiting_retry" %}
+                                <span class="label label-warning">{% icon "repeat" %} {% trans "will be retried" %}</span>
+                            {% elif mail.status == "failed" %}
+                                <span class="label label-danger">{% icon "warning" %} {% trans "failed" %}</span>
+                            {% elif mail.status == "bounced" %}
+                                <span class="label label-danger">{% icon "ban" %} {% trans "bounced" %}</span>
+                            {% elif mail.status == "sent" %}
+                                <span class="label label-success">{% icon "check" %} {% trans "sent" %}</span>
+                            {% endif %}
+                        </dd>
+                        <dt>{% trans "Creation" %}</dt>
+                        <dd>{{ mail.created|date:"SHORT_DATETIME_FORMAT" }}</dd>
+                        {% if mail.sent %}
+                            <dt>{% trans "Sent" %}</dt>
+                            <dd>{{ mail.sent|date:"SHORT_DATETIME_FORMAT" }}</dd>
+                        {% endif %}
+                        {% if mail.retry_after and mail.status == "awaiting_retry" %}
+                            <dt>{% trans "Next attempt (estimate)" %}</dt>
+                            <dd>{{ mail.retry_after|date:"SHORT_DATETIME_FORMAT" }}</dd>
+                        {% endif %}
+                        {% if mail.event %}
+                            <dt>{% trans "Event" %}</dt>
+                            <dd>
+                                <a href="{% url "control:event.index" organizer=request.organizer.slug event=mail.event.slug %}">
+                                    {{ mail.event }}
+                                </a>
+                            </dd>
+                        {% endif %}
+                        {% if mail.order %}
+                            <dt>{% trans "Order" %}</dt>
+                            <dd>
+                                <a href="{% url "control:event.order" organizer=request.organizer.slug event=mail.event.slug code=mail.order.code %}">
+                                    {{ mail.order.code }}</a>{% if mail.orderposition %}-
+                                {{ mail.orderposition.positionid }}{% endif %}
+                            </dd>
+                        {% endif %}
+                        {% if mail.customer %}
+                            <dt>{% trans "Customer" %}</dt>
+                            <dd>
+                                {% icon "user fa-fw" %}
+                                <a href="{% url "control:organizer.customer" organizer=request.organizer.slug customer=mail.customer.identifier %}">
+                                    {{ mail.customer }}
+                                </a>
+                            </dd>
+                        {% endif %}
+                    </dl>
+                </div>
+                {% if mail.actual_attachments %}
+                    <div class="col-lg-5 col-md-12">
+                        <strong>{% trans "Attachments" %}</strong><br>
+                        <ul class="list-unstyled">
+                            {% for a in mail.actual_attachments %}
+                                <li>
+                                    {% if a.type == "text/calendar" %}
+                                        {% icon "calendar-plus-o fa-fw" %}
+                                    {% elif a.type == "application/pdf" %}
+                                        {% icon "file-pdf-o fa-fw" %}
+                                    {% elif "image/" in a.type %}
+                                        {% icon "file-image-o fa-fw" %}
+                                    {% elif "msword" in a.type or "document" in a.type %}
+                                        {% icon "file-word-o fa-fw" %}
+                                    {% elif "excel" in a.type or "spreadsheet" in a.type %}
+                                        {% icon "file-excel-o fa-fw" %}
+                                    {% elif "powerpoint" in a.type or "presentation" in a.type %}
+                                        {% icon "file-powerpoint-o fa-fw" %}
+                                    {% elif "pkpass" in a.type %}
+                                        {% icon "qrcode fa-fw" %}
+                                    {% else %}
+                                        {% icon "file-o fa-fw" %}
+                                    {% endif %}
+                                    {{ a.name }}
+                                    <span class="text-muted">
+                                        ({{ a.size|filesizeformat }})
+                                    </span>
+                                </li>
+                            {% endfor %}
+                        </ul>
+                    </div>
+                {% endif %}
+            </div>
+        </div>
+    </div>
+    <div>
+        <ul class="nav nav-tabs" role="tablist">
+            {% if mail.is_failed %}
+                <li role="presentation" class="active">
+                    <a href="#tab-error" role="tab" data-toggle="tab">
+                        <span class="fa fa-warning"></span>
+                        {% trans "Error" %}
+                    </a>
+                </li>
+            {% endif %}
+            {% if mail.body_html %}
+                <li role="presentation"
+                    {% if not mail.is_failed %}class="active"{% endif %}>
+                    <a href="#tab-html" role="tab" data-toggle="tab">
+                        <span class="fa fa-eye"></span>
+                        {% trans "HTML content" %}
+                    </a>
+                </li>
+            {% endif %}
+            <li role="presentation"
+                {% if not mail.is_failed and not mail.body_html %}class="active"{% endif %}>
+                <a href="#tab-text" role="tab" data-toggle="tab">
+                    <span class="fa fa-file-text-o"></span>
+                    {% trans "Text content" %}
+                </a>
+            </li>
+            <li role="presentation">
+                <a href="#tab-headers" role="tab" data-toggle="tab">
+                    <span class="fa fa-code"></span>
+                    {% trans "Headers" %}
+                </a>
+            </li>
+        </ul>
+
+        <div class="tab-content">
+            {% if mail.is_failed %}
+                <div role="tabpanel" class="tab-pane active" id="tab-error">
+                    <strong>
+                        {{ mail.error }}
+                    </strong>
+                    <pre>{{ mail.error_detail }}</pre>
+                </div>
+            {% endif %}
+            {% if mail.body_html %}
+                <div role="tabpanel"
+                     class="tab-pane {% if not mail.is_failed %}active{% endif %}"
+                     id="tab-html">
+                    {{ data_url|json_script:"mail_body_html" }}
+                </div>
+            {% endif %}
+            <div role="tabpanel"
+                 class="tab-pane {% if not mail.is_failed and not mail.body_html %}active{% endif %}"
+                 id="tab-text">
+                <pre><code>{{ mail.body_plain }}</code></pre>
+            </div>
+            <div role="tabpanel"
+                 class="tab-pane"
+                 id="tab-headers">
+                <pre><code>{% for k, v in mail.headers.items %}{{ k }}: {{ v }}<br>{% endfor %}</code></pre>
+                <p class="text-muted">
+                    {% trans "Additional headers will be added by the mail server and are not visible here." %}
+                </p>
+            </div>
+        </div>
+
+    </div>
+    {% compress js %}
+        <script type="text/javascript" src="{% static "pretixcontrol/js/ui/outgoingmail.js" %}"></script>
+    {% endcompress %}
+{% endblock %}
diff --git a/src/pretix/control/templates/pretixcontrol/organizers/outgoing_mails.html b/src/pretix/control/templates/pretixcontrol/organizers/outgoing_mails.html
new file mode 100644
index 0000000000..1384e2a440
--- /dev/null
+++ b/src/pretix/control/templates/pretixcontrol/organizers/outgoing_mails.html
@@ -0,0 +1,174 @@
+{% extends "pretixcontrol/organizers/base.html" %}
+{% load i18n %}
+{% load bootstrap3 %}
+{% load urlreplace %}
+{% load icon %}
+{% block inner %}
+    <h1>
+        {% trans "Outgoing emails" %}
+    </h1>
+    <p>
+        {% blocktrans trimmed with days=days %}
+            This is an overview of all emails sent by your organizer account in the last {{ days }} days.
+        {% endblocktrans %}
+    </p>
+    {% if mails|length == 0 and not filter_form.filtered %}
+        <div class="empty-collection">
+            <p>
+                {% blocktrans trimmed %}
+                    You haven't sent any emails recently.
+                {% endblocktrans %}
+            </p>
+        </div>
+    {% else %}
+        <div class="panel panel-default">
+            <div class="panel-heading">
+                <h3 class="panel-title">{% trans "Filter" %}</h3>
+            </div>
+            <form class="panel-body filter-form" action="" method="get">
+                <div class="row">
+                    <div class="col-md-4 col-sm-6 col-xs-12">
+                        {% bootstrap_field filter_form.query %}
+                    </div>
+                    <div class="col-md-3 col-sm-6 col-xs-12">
+                        {% bootstrap_field filter_form.status %}
+                    </div>
+                    <div class="col-md-5 col-sm-6 col-xs-12">
+                        {% bootstrap_field filter_form.event %}
+                    </div>
+                </div>
+                <div class="text-right">
+                    <button class="btn btn-primary btn-lg" type="submit">
+                        <span class="fa fa-filter"></span>
+                        {% trans "Filter" %}
+                    </button>
+                </div>
+            </form>
+        </div>
+        <form action="{% url "control:organizer.outgoingmails.bulk_action" organizer=request.organizer.slug %}" method="post">
+            {% csrf_token %}
+            {% for field in filter_form %}
+                {{ field.as_hidden }}
+            {% endfor %}
+            <div class="table-responsive">
+                <table class="table table-condensed table-hover table-quotas">
+                    <thead>
+                    <tr>
+                        <th>
+                            <label aria-label="{% trans "select all rows for batch-operation" %}"
+                                   class="batch-select-label"><input type="checkbox" data-toggle-table/></label>
+                        </th>
+                        <th>{% trans "Subject" %}</th>
+                        <th>{% trans "Recipients" %}</th>
+                        <th>{% trans "Context" %}</th>
+                        <th>{% trans "Status" %}</th>
+                        <th>{% trans "Date" %}
+                            <a href="?{% url_replace request 'ordering' '-date' %}"><i
+                                    class="fa fa-caret-down"></i></a>
+                            <a href="?{% url_replace request 'ordering' 'date' %}"><i class="fa fa-caret-up"></i></a>
+                        </th>
+                        <th></th>
+                    </tr>
+                    {% if page_obj.paginator.num_pages > 1 %}
+                        <tr class="table-select-all warning hidden">
+                            <td>
+                                <input type="checkbox" name="__ALL" id="__all"
+                                       data-results-total="{{ page_obj.paginator.count }}">
+                            </td>
+                            <td colspan="7">
+                                <label for="__all">
+                                    {% trans "Select all results on other pages as well" %}
+                                </label>
+                            </td>
+                        </tr>
+                    {% endif %}
+                    </thead>
+                    <tbody>
+                    {% for m in mails %}
+                        <tr>
+                            <td>
+                                <label aria-label="{% trans "select row for batch-operation" %}"
+                                       class="batch-select-label"><input type="checkbox" name="outgoingmail"
+                                                                         class="batch-select-checkbox"
+                                                                         value="{{ m.pk }}"/></label>
+                            </td>
+                            <td>
+                                <a href="{% url "control:organizer.outgoingmail" organizer=request.organizer.slug mail=m.id %}">
+                                    {{ m.subject }}
+                                </a>
+                            </td>
+                            <td>
+                                {{ m.to|join:", " }}
+                                {% if m.cc %}
+                                    <br><small class="text-muted">{% trans "Cc" context "email" %}: {{ m.cc|join:", " }}</small>
+                                {% endif %}
+                                {% if m.bcc %}
+                                    <br><small class="text-muted">{% trans "Bcc" context "email" %} {{ m.bcc|join:", " }}</small>
+                                {% endif %}
+                            </td>
+                            <td>
+                                {% if m.event %}
+                                    <div>
+                                        {% icon "calendar fa-fw" %}
+                                        <a href="{% url "control:event.index" organizer=request.organizer.slug event=m.event.slug %}">
+                                            {{ m.event }}
+                                        </a>
+                                    </div>
+                                {% endif %}
+                                {% if m.order %}
+                                    <div>
+                                        {% icon "shopping-cart fa-fw" %}
+                                        <a href="{% url "control:event.order" organizer=request.organizer.slug event=m.event.slug code=m.order.code %}">
+                                            {{ m.order.code }}</a>{% if m.orderposition %}-{{ m.orderposition.positionid }}{% endif %}
+                                    </div>
+                                {% endif %}
+                                {% if m.customer %}
+                                    <div>
+                                        {% icon "user fa-fw" %}
+                                        <a href="{% url "control:organizer.customer" organizer=request.organizer.slug customer=m.customer.identifier %}">
+                                            {{ m.customer }}
+                                        </a>
+                                    </div>
+                                {% endif %}
+                            </td>
+                            <td>
+                                {% if m.status == "queued" %}
+                                    <span class="label label-info">{% icon "clock" %} {% trans "queued" %}</span>
+                                {% elif m.status == "inflight" %}
+                                    <span class="label label-info">{% icon "send" %} {% trans "being sent" %}</span>
+                                {% elif m.status == "awaiting_retry" %}
+                                    <span class="label label-warning">{% icon "repeat" %} {% trans "will be retried" %}</span>
+                                {% elif m.status == "failed" %}
+                                    <span class="label label-danger">{% icon "warning" %} {% trans "failed" %}</span>
+                                {% elif m.status == "bounced" %}
+                                    <span class="label label-danger">{% icon "ban" %} {% trans "bounced" %}</span>
+                                {% elif m.status == "sent" %}
+                                    <span class="label label-success">{% icon "check" %} {% trans "sent" %}</span>
+                                {% endif %}
+                            </td>
+                            <td>
+                                {{ m.created|date:"SHORT_DATETIME_FORMAT" }}
+                                {% if m.sent %}
+                                    <br>
+                                    <small class="text-muted">{% trans "Sent:" %} {{ m.sent|date:"SHORT_DATETIME_FORMAT" }}</small>
+                                {% endif %}
+                            </td>
+                            <td class="text-right flip">
+                                <a href="{% url "control:organizer.outgoingmail" organizer=request.organizer.slug mail=m.id %}"
+                                   class="btn btn-default btn-sm">{% icon "eye" %}</a>
+                            </td>
+                        </tr>
+                    {% endfor %}
+                    </tbody>
+                </table>
+            </div>
+            <div class="batch-select-actions">
+                <button type="submit" class="btn btn-primary btn-save" name="action" value="retry">
+                    {% icon "repeat" %}
+                    {% trans "Retry failed" %}
+                </button>
+            </div>
+        </form>
+        {% include "pretixcontrol/pagination.html" %}
+    {% endif %}
+{% endblock %}
diff --git a/src/pretix/control/urls.py b/src/pretix/control/urls.py
index d310572e30..9d92c90815 100644
--- a/src/pretix/control/urls.py
+++ b/src/pretix/control/urls.py
@@ -38,8 +38,9 @@ from django.views.generic.base import RedirectView
 
 from pretix.control.views import (
     auth, checkin, dashboards, datasync, discounts, event, geo,
-    global_settings, item, main, modelimport, oauth, orders, organizer, pdf,
-    search, shredder, subevents, typeahead, user, users, vouchers, waitinglist,
+    global_settings, item, mail, main, modelimport, oauth, orders, organizer,
+    pdf, search, shredder, subevents, typeahead, user, users, vouchers,
+    waitinglist,
 )
 
 urlpatterns = [
@@ -240,6 +241,9 @@ urlpatterns = [
             name='organizer.gate.edit'),
     re_path(r'^organizer/(?P<organizer>[^/]+)/gate/(?P<gate>[^/]+)/delete$', organizer.GateDeleteView.as_view(),
             name='organizer.gate.delete'),
+    re_path(r'^organizer/(?P<organizer>[^/]+)/outgoingmails$', mail.OutgoingMailListView.as_view(), name='organizer.outgoingmails'),
+    re_path(r'^organizer/(?P<organizer>[^/]+)/outgoingmail/bulk_action$', mail.OutgoingMailBulkAction.as_view(), name='organizer.outgoingmails.bulk_action'),
+    re_path(r'^organizer/(?P<organizer>[^/]+)/outgoingmail/(?P<mail>[0-9]+)/$', mail.OutgoingMailDetailView.as_view(), name='organizer.outgoingmail'),
     re_path(r'^organizer/(?P<organizer>[^/]+)/teams$', organizer.TeamListView.as_view(), name='organizer.teams'),
     re_path(r'^organizer/(?P<organizer>[^/]+)/team/add$', organizer.TeamCreateView.as_view(), name='organizer.team.add'),
     re_path(r'^organizer/(?P<organizer>[^/]+)/team/(?P<team>[^/]+)/$', organizer.TeamMemberView.as_view(),
diff --git a/src/pretix/control/views/mail.py b/src/pretix/control/views/mail.py
new file mode 100644
index 0000000000..a8a439bb41
--- /dev/null
+++ b/src/pretix/control/views/mail.py
@@ -0,0 +1,159 @@
+#
+# This file is part of pretix (Community Edition).
+#
+# Copyright (C) 2014-2020  Raphael Michel and contributors
+# Copyright (C) 2020-today pretix 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/>.
+#
+import base64
+import logging
+
+from django.conf import settings
+from django.contrib import messages
+from django.core.exceptions import BadRequest
+from django.db import transaction
+from django.shortcuts import get_object_or_404, redirect
+from django.urls import reverse
+from django.utils.functional import cached_property
+from django.utils.translation import ngettext
+from django.views import View
+from django.views.generic import DetailView, ListView
+
+from pretix.base.middleware import _merge_csp, _parse_csp, _render_csp
+from pretix.base.models import OutgoingMail
+from pretix.base.services.mail import mail_send_task
+from pretix.control.forms.filter import OutgoingMailFilterForm
+from pretix.control.permissions import OrganizerPermissionRequiredMixin
+from pretix.control.views.organizer import OrganizerDetailViewMixin
+
+logger = logging.getLogger(__name__)
+
+
+class OutgoingMailQueryMixin:
+
+    @cached_property
+    def request_data(self):
+        if self.request.method == "POST":
+            d = self.request.POST
+        else:
+            d = self.request.GET
+        d = d.copy()
+        return d
+
+    @cached_property
+    def filter_form(self):
+        return OutgoingMailFilterForm(
+            data=self.request_data,
+            request=self.request,
+        )
+
+    def get_queryset(self):
+        qs = self.request.organizer.outgoing_mails.select_related(
+            'event', 'order', 'orderposition', 'customer'
+        )
+
+        if 'outgoingmail' in self.request_data and '__ALL' not in self.request_data:
+            qs = qs.filter(
+                id__in=self.request_data.getlist('outgoingmail')
+            )
+        elif self.request.method == 'GET' or '__ALL' in self.request_data:
+            if self.filter_form.is_valid():
+                qs = self.filter_form.filter_qs(qs)
+        else:
+            raise BadRequest("No mails selected")
+
+        return qs
+
+
+class OutgoingMailListView(OutgoingMailQueryMixin, OrganizerDetailViewMixin, OrganizerPermissionRequiredMixin, ListView):
+    model = OutgoingMail
+    template_name = 'pretixcontrol/organizers/outgoing_mails.html'
+    # Assume "the highest" permission level for now because emails could belog to any event, order, or customer.
+    # We plan to add a special permissoin in the future
+    permission = 'can_change_organizer_settings'
+    context_object_name = 'mails'
+    paginate_by = 100
+
+    def get_context_data(self, **kwargs):
+        ctx = super().get_context_data(**kwargs)
+        ctx['filter_form'] = self.filter_form
+        ctx['days'] = int(settings.OUTGOING_MAIL_RETENTION / (24 * 3600))
+        return ctx
+
+
+class OutgoingMailDetailView(OrganizerDetailViewMixin, OrganizerPermissionRequiredMixin, DetailView):
+    model = OutgoingMail
+    template_name = 'pretixcontrol/organizers/outgoing_mail.html'
+    permission = 'can_change_organizer_settings'
+    context_object_name = 'mail'
+
+    def get_object(self, queryset=None):
+        return get_object_or_404(OutgoingMail, organizer=self.request.organizer, pk=self.kwargs.get('mail'))
+
+    def dispatch(self, request, *args, **kwargs):
+        response = super().dispatch(request, *args, **kwargs)
+        if 'Content-Security-Policy' in response:
+            h = _parse_csp(response['Content-Security-Policy'])
+        else:
+            h = {}
+        csps = {
+            'frame-src': ['data:'],
+        }
+        _merge_csp(h, csps)
+        response['Content-Security-Policy'] = _render_csp(h)
+        return response
+
+    def get_context_data(self, **kwargs):
+        ctx = super().get_context_data(**kwargs)
+        if self.object.body_html:
+            ctx['data_url'] = "data:text/html;charset=utf-8;base64," + base64.b64encode(self.object.body_html.encode()).decode()
+        return ctx
+
+
+class OutgoingMailBulkAction(OutgoingMailQueryMixin, OrganizerPermissionRequiredMixin, OrganizerDetailViewMixin, View):
+    permission = 'can_change_organizer_settings'
+
+    @transaction.atomic
+    def post(self, request, *args, **kwargs):
+        if request.POST.get('action') == 'retry':
+            ids = set(
+                self.get_queryset().filter(status=OutgoingMail.STATUS_FAILED).values_list("pk", flat=True)
+            )
+            with transaction.atomic():
+                OutgoingMail.objects.filter(pk__in=ids).update(
+                    status=OutgoingMail.STATUS_QUEUED,
+                    sent=None,
+                )
+                self.request.organizer.log_action(
+                    'pretix.organizer.outgoingmails.retried', user=self.request.user, data={
+                        'mails': list(ids)
+                    }, save=False
+                )
+            for i in ids:
+                mail_send_task.apply_async(kwargs={"outgoing_mail": i})
+
+            messages.success(request, ngettext(
+                "A retry of one email was scheduled.",
+                "A retry of {num} emails was scheduled.",
+                len(ids),
+            ).format(num=len(ids)))
+        return redirect(self.get_success_url())
+
+    def get_success_url(self) -> str:
+        return reverse('control:organizer.outgoingmails', kwargs={
+            'organizer': self.request.organizer.slug,
+        })
diff --git a/src/pretix/helpers/database.py b/src/pretix/helpers/database.py
index 6caf7499f6..1289f4f1af 100644
--- a/src/pretix/helpers/database.py
+++ b/src/pretix/helpers/database.py
@@ -25,7 +25,7 @@ from django.conf import settings
 from django.core.exceptions import FieldDoesNotExist, ImproperlyConfigured
 from django.db import connection, transaction
 from django.db.models import (
-    Aggregate, Expression, F, Field, Lookup, OrderBy, Value,
+    Aggregate, Expression, F, Field, JSONField, Lookup, OrderBy, Value,
 )
 from django.utils.functional import lazy
 
@@ -154,6 +154,19 @@ class NotEqual(Lookup):
         return '%s <> %s' % (lhs, rhs), params
 
 
+@JSONField.register_lookup
+class ContainsString(Lookup):
+    lookup_name = 'containsstring'
+
+    def as_sql(self, compiler, connection):
+        if connection.vendor != "postgresql":
+            raise NotImplementedError("Lookup in JSON Array not supported on this database")
+        lhs, lhs_params = self.process_lhs(compiler, connection)
+        rhs, rhs_params = self.process_rhs(compiler, connection)
+        params = lhs_params + rhs_params
+        return '%s ? %s' % (lhs, rhs), params
+
+
 class PostgresWindowFrame(Expression):
     template = "%(frame_type)s BETWEEN %(start)s AND %(end)s"
 
diff --git a/src/pretix/static/pretixcontrol/js/ui/outgoingmail.js b/src/pretix/static/pretixcontrol/js/ui/outgoingmail.js
new file mode 100644
index 0000000000..d82803bafb
--- /dev/null
+++ b/src/pretix/static/pretixcontrol/js/ui/outgoingmail.js
@@ -0,0 +1,42 @@
+function is_sandbox_supported() {
+    const iframe = document.createElement('iframe');
+    return 'sandbox' in iframe;
+}
+
+function safe_render(url, parent) {
+    const height = (
+        window.innerHeight - parent.parent().get(0).getBoundingClientRect().top - document.querySelector("footer").getBoundingClientRect().height - 20
+    ) + "px";
+
+    const iframe = (
+        // Per the HTML spec, a data: URL in an iframe is treated as its own origin:
+        // https://github.com/whatwg/html/pull/1756
+        // It is unclear, if Firefox complies, and the behaviour around data URLs is quite wild:
+        // https://github.com/whatwg/html/issues/12091
+        // Together with the sandbox attribute disallowing all JavaScript, and the fact
+        // that we sanitize the HTML before we even save it to the database, this should
+        // still be the safest way to render HTML in the context of our backend.
+        $("<iframe>")
+            .height(height)
+            .attr("class", "html-email")
+            .attr("src", url)
+            .attr("sandbox", "allow-popups allow-popups-to-escape-sandbox")
+            .attr("csp", "script-src 'none'; font-src 'none'; connect-src 'none'; form-action 'none'")  // respected only by chrome
+            .prop("credentialless", true)  // respected only by chrome
+    );
+
+    console.log(parent, iframe);
+    parent.append(iframe);
+}
+
+$(function () {
+    const script_element = $("#mail_body_html");
+    if (!script_element.length) return;
+    if (!is_sandbox_supported()) {
+        // Browser is too old for <iframe sandbox>
+        $(script_element.parent()).text("Please switch to a modern browser to view HTML content safely.");
+        return;
+    }
+
+    safe_render(JSON.parse(script_element.html()), script_element.parent());
+});
diff --git a/src/pretix/static/pretixcontrol/scss/_mail_preview.scss b/src/pretix/static/pretixcontrol/scss/_mail_preview.scss
index d97152cc01..0856cc6699 100644
--- a/src/pretix/static/pretixcontrol/scss/_mail_preview.scss
+++ b/src/pretix/static/pretixcontrol/scss/_mail_preview.scss
@@ -91,3 +91,8 @@ div.mail-preview {
     text-align: right;
   }
 }
+
+iframe.html-email {
+  border: 0;
+  width: 100%;
+}
\ No newline at end of file