diff --git a/src/pretix/base/models/orders.py b/src/pretix/base/models/orders.py
index 8854151403..7ac8beff17 100644
--- a/src/pretix/base/models/orders.py
+++ b/src/pretix/base/models/orders.py
@@ -1199,6 +1199,8 @@ class Order(LockModel, LoggedModel):
                         '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 [],
                     }
                 )
 
@@ -2857,6 +2859,8 @@ class OrderPosition(AbstractPosition):
                         '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': [],
                     }
                 )
 
diff --git a/src/pretix/base/models/waitinglist.py b/src/pretix/base/models/waitinglist.py
index df5d979922..2b9b48df75 100644
--- a/src/pretix/base/models/waitinglist.py
+++ b/src/pretix/base/models/waitinglist.py
@@ -286,6 +286,8 @@ class WaitingListEntry(LoggedModel):
                         '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 [],
                     }
                 )
 
diff --git a/src/pretix/control/templates/pretixcontrol/order/mail_history.html b/src/pretix/control/templates/pretixcontrol/order/mail_history.html
index e3f72f5437..ade4baed66 100644
--- a/src/pretix/control/templates/pretixcontrol/order/mail_history.html
+++ b/src/pretix/control/templates/pretixcontrol/order/mail_history.html
@@ -51,6 +51,41 @@
                                 {{ log.parsed_data.subject }}</strong>
                         </p>
                         <pre>{{ log.parsed_data.message }}</pre>
+                        <ul class="list-unstyled">
+                            {% if log.parsed_data.attach_tickets %}
+                                <li><span class="fa fa-files-o fa-fw"></span> {% trans "Tickets" %}</li>
+                            {% endif %}
+                            {% if log.parsed_data.attach_ical %}
+                                <li><span class="fa fa-calendar-o fa-fw"></span> {% trans "Calendar invite" %}</li>
+                            {% endif %}
+                            {% if log.parsed_data.invoices %}
+                                {% for i in log.parsed_invoices %}
+                                    <li>
+                                        <span class="fa fa-file-o fa-fw"></span>
+                                        <a href="{% url "control:event.invoice.download" invoice=i.pk event=request.event.slug organizer=request.event.organizer.slug %}" target="_blank">
+                                            {% if i.is_cancellation %}{% trans "Cancellation" context "invoice" %}{% else %}{% trans "Invoice" %}{% endif %}
+                                            {{ i.number }}
+                                        </a>
+                                    </li>
+                                {% endfor %}
+                            {% endif %}
+                            {% if log.parsed_data.attach_other_files %}
+                                {% for f in log.parsed_other_files %}
+                                    <li>
+                                        <span class="fa fa-file-o fa-fw"></span>
+                                        {{ f }}
+                                    </li>
+                                {% endfor %}
+                            {% endif %}
+                            {% if log.parsed_data.attach_cached_files %}
+                                {% for f in log.parsed_data.attach_cached_files %}
+                                    <li>
+                                        <span class="fa fa-file-o fa-fw"></span>
+                                        {{ f }}
+                                    </li>
+                                {% endfor %}
+                            {% endif %}
+                        </ul>
                     {% endif %}
                 </li>
             {% endfor %}
diff --git a/src/pretix/control/views/orders.py b/src/pretix/control/views/orders.py
index 82bd4ca600..6b97bbc1ed 100644
--- a/src/pretix/control/views/orders.py
+++ b/src/pretix/control/views/orders.py
@@ -135,6 +135,7 @@ from pretix.control.views import PaginationMixin
 from pretix.helpers import OF_SELF
 from pretix.helpers.compat import CompatDeleteView
 from pretix.helpers.format import SafeFormatter, format_map
+from pretix.helpers.hierarkey import clean_filename
 from pretix.helpers.safedownload import check_token
 from pretix.presale.signals import question_form_fields
 
@@ -2461,6 +2462,20 @@ class OrderEmailHistory(EventPermissionRequiredMixin, OrderViewMixin, ListView):
         )
         return qs
 
+    def get_context_data(self, **kwargs):
+        ctx = super().get_context_data(**kwargs)
+        for l in ctx["logs"]:
+            if l.parsed_data.get("invoices"):
+                l.parsed_invoices = Invoice.objects.filter(
+                    event=self.request.event,
+                    pk__in=l.parsed_data["invoices"],
+                )
+            if l.parsed_data.get("attach_other_files"):
+                l.parsed_other_files = [
+                    clean_filename(os.path.basename(f)) for f in l.parsed_data["attach_other_files"]
+                ]
+        return ctx
+
 
 class AnswerDownload(EventPermissionRequiredMixin, OrderViewMixin, ListView):
     permission = 'can_view_orders'
diff --git a/src/pretix/plugins/sendmail/tasks.py b/src/pretix/plugins/sendmail/tasks.py
index c5b8792899..08ae713e73 100644
--- a/src/pretix/plugins/sendmail/tasks.py
+++ b/src/pretix/plugins/sendmail/tasks.py
@@ -38,7 +38,9 @@ from i18nfield.strings import LazyI18nString
 
 from pretix.base.email import get_email_context
 from pretix.base.i18n import language
-from pretix.base.models import Checkin, Event, InvoiceAddress, Order, User
+from pretix.base.models import (
+    CachedFile, Checkin, Event, InvoiceAddress, Order, User,
+)
 from pretix.base.services.mail import SendMailException, mail
 from pretix.base.services.tasks import ProfiledEventTask
 from pretix.celery_app import app
@@ -56,6 +58,7 @@ def send_mails_to_orders(event: Event, user: int, subject: dict, message: dict,
     orders = Order.objects.filter(pk__in=objects, event=event)
     subject = LazyI18nString(subject)
     message = LazyI18nString(message)
+    attachments_for_log = [cf.filename for cf in CachedFile.objects.filter(pk__in=attachments)] if attachments else []
 
     for o in orders:
         send_to_order = recipients in ('both', 'orders')
@@ -134,7 +137,11 @@ def send_mails_to_orders(event: Event, user: int, subject: dict, message: dict,
                                 '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
+                                'recipient': p.attendee_email,
+                                'attach_tickets': attach_tickets,
+                                'attach_ical': attach_ical,
+                                'attach_other_files': [],
+                                'attach_cached_files': attachments_for_log,
                             }
                         )
                 except SendMailException:
@@ -162,7 +169,11 @@ def send_mails_to_orders(event: Event, user: int, subject: dict, message: dict,
                         data={
                             'subject': format_map(subject.localize(o.locale), email_context),
                             'message': format_map(message.localize(o.locale), email_context),
-                            'recipient': o.email
+                            'recipient': o.email,
+                            'attach_tickets': attach_tickets,
+                            'attach_ical': attach_ical,
+                            'attach_other_files': [],
+                            'attach_cached_files': attachments_for_log,
                         }
                     )
             except SendMailException:
diff --git a/src/pretix/plugins/sendmail/templates/pretixplugins/sendmail/send_form.html b/src/pretix/plugins/sendmail/templates/pretixplugins/sendmail/send_form.html
index 308009a56b..9ba3dbc1db 100644
--- a/src/pretix/plugins/sendmail/templates/pretixplugins/sendmail/send_form.html
+++ b/src/pretix/plugins/sendmail/templates/pretixplugins/sendmail/send_form.html
@@ -45,27 +45,28 @@
                         <div lang="{{ locale }}" class="mail-preview">
                             <strong>{{ out.subject|safe }}</strong><br><br>
                             {{ out.html|safe }}
-                            {% if out.attachment %}
-                                <p>
-                                    <a href="{% url 'cachedfile.download' id=out.attachment.id %}" class="btn btn-default"
-                                            target="_blank">
-                                        <span class="fa fa-file" aria-hidden="true"></span>
-                                        {{ out.attachment.filename }}
-                                    </a>
-                                </p>
-                            {% endif %}
-                            {% if form.cleaned_data.attach_tickets %}
-                                <p>
-                                    <span class="fa fa-file" aria-hidden="true"></span>
-                                    {% trans "Tickets" %}
-                                </p>
-                            {% endif %}
-                            {% if form.cleaned_data.attach_ical %}
-                                <p>
-                                    <span class="fa fa-file" aria-hidden="true"></span>
-                                    {% trans "Attach calendar files" %}
-                                </p>
-                            {% endif %}
+                            <ul class="list-unstyled">
+                                {% if out.attachment %}
+                                    <li>
+                                        <span class="fa fa-file-o fa-fw" aria-hidden="true"></span>
+                                        <a href="{% url 'cachedfile.download' id=out.attachment.id %}" target="_blank">
+                                            {{ out.attachment.filename }}
+                                        </a>
+                                    </li>
+                                {% endif %}
+                                {% if form.cleaned_data.attach_tickets %}
+                                    <li>
+                                        <span class="fa fa-file-o fa-fw" aria-hidden="true"></span>
+                                        {% trans "Tickets" %}
+                                    </li>
+                                {% endif %}
+                                {% if form.cleaned_data.attach_ical %}
+                                    <li>
+                                        <span class="fa fa-calendar-o fa-fw" aria-hidden="true"></span>
+                                        {% trans "Attach calendar files" %}
+                                    </li>
+                                {% endif %}
+                            </ul>
                         </div>
                     {% endfor %}
                 </div>