diff --git a/src/pretix/base/email.py b/src/pretix/base/email.py
index feeded31f..5e2fa5c5e 100644
--- a/src/pretix/base/email.py
+++ b/src/pretix/base/email.py
@@ -520,20 +520,20 @@ def base_placeholders(sender, **kwargs):
             lambda event: (event if not event.has_subevents or not event.subevents.exists() else event.subevents.first()).get_date_from_display()
         ),
         SimpleFunctionalMailTextPlaceholder(
-            'url_remove', ['waiting_list_entry', 'event'],
-            lambda waiting_list_entry, event: build_absolute_uri(
+            'url_remove', ['waiting_list_voucher', 'event'],
+            lambda waiting_list_voucher, event: build_absolute_uri(
                 event, 'presale:event.waitinglist.remove'
-            ) + '?voucher=' + waiting_list_entry.voucher.code,
+            ) + '?voucher=' + waiting_list_voucher.code,
             lambda event: build_absolute_uri(
                 event,
                 'presale:event.waitinglist.remove',
             ) + '?voucher=68CYU2H6ZTP3WLK5',
         ),
         SimpleFunctionalMailTextPlaceholder(
-            'url', ['waiting_list_entry', 'event'],
-            lambda waiting_list_entry, event: build_absolute_uri(
+            'url', ['waiting_list_voucher', 'event'],
+            lambda waiting_list_voucher, event: build_absolute_uri(
                 event, 'presale:event.redeem'
-            ) + '?voucher=' + waiting_list_entry.voucher.code,
+            ) + '?voucher=' + waiting_list_voucher.code,
             lambda event: build_absolute_uri(
                 event,
                 'presale:event.redeem',
diff --git a/src/pretix/base/models/waitinglist.py b/src/pretix/base/models/waitinglist.py
index 5e9002e29..98571d39b 100644
--- a/src/pretix/base/models/waitinglist.py
+++ b/src/pretix/base/models/waitinglist.py
@@ -20,6 +20,7 @@
 # <https://www.gnu.org/licenses/>.
 #
 from datetime import timedelta
+from typing import Any, Dict, Union
 
 from django.core.exceptions import ObjectDoesNotExist, ValidationError
 from django.db import models, transaction
@@ -27,14 +28,16 @@ from django.db.models import F, Q, Sum
 from django.utils.timezone import now
 from django.utils.translation import gettext_lazy as _, pgettext_lazy
 from django_scopes import ScopedManager
+from i18nfield.strings import LazyI18nString
 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 Voucher
-from pretix.base.services.mail import mail
+from pretix.base.models import User, Voucher
+from pretix.base.services.mail import SendMailException, mail, render_mail
 from pretix.base.settings import PERSON_NAME_SCHEMES
 
+from ...helpers.format import format_map
 from .base import LoggedModel
 from .event import Event, SubEvent
 from .items import Item, ItemVariation
@@ -213,15 +216,74 @@ class WaitingListEntry(LoggedModel):
             self.voucher = v
             self.save()
 
+        self.send_mail(
+            self.event.settings.mail_subject_waiting_list,
+            self.event.settings.mail_text_waiting_list,
+            get_email_context(
+                event=self.event,
+                waiting_list_entry=self,
+                waiting_list_voucher=v,
+                event_or_subevent=self.subevent or self.event,
+            ),
+            user=user,
+            auth=auth,
+        )
+
+    def send_mail(self, subject: Union[str, LazyI18nString], template: Union[str, LazyI18nString],
+                  context: Dict[str, Any]=None, log_entry_type: str='pretix.waitinglist.email.sent',
+                  user: User=None, headers: dict=None, sender: str=None, auth=None, auto_email=True,
+                  attach_other_files: list=None, attach_cached_files: list=None):
+        """
+        Sends an email to the entry's contact address.
+
+        * Call ``pretix.base.services.mail.mail`` with useful values for the ``event``, ``locale``, and ``recipient``
+          parameters.
+
+        * Create a ``LogEntry`` with the email contents.
+
+        :param subject: Subject of the email
+        :param template: LazyI18nString or template filename, see ``pretix.base.services.mail.mail`` for more details
+        :param context: Dictionary to use for rendering the template
+        :param log_entry_type: Key to be used for the log entry
+        :param user: Administrative user who triggered this mail to be sent
+        :param headers: Dictionary with additional mail headers
+        :param sender: Custom email sender.
+        """
+        if not self.email:
+            return
+
+        for k, v in self.event.meta_data.items():
+            context['meta_' + k] = v
+
         with language(self.locale, self.event.settings.region):
-            mail(
-                self.email,
-                self.event.settings.mail_subject_waiting_list,
-                self.event.settings.mail_text_waiting_list,
-                get_email_context(event=self.event, waiting_list_entry=self),
-                self.event,
-                locale=self.locale
-            )
+            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,
+                    }
+                )
 
     @staticmethod
     def clean_itemvar(event, item, variation):
diff --git a/src/pretix/control/forms/event.py b/src/pretix/control/forms/event.py
index 0885e03d6..98843b979 100644
--- a/src/pretix/control/forms/event.py
+++ b/src/pretix/control/forms/event.py
@@ -1209,8 +1209,8 @@ class MailSettingsForm(SettingsForm):
         'mail_text_resend_link': ['event', 'order'],
         'mail_subject_resend_link': ['event', 'order'],
         'mail_subject_resend_link_attendee': ['event', 'order'],
-        'mail_text_waiting_list': ['event', 'waiting_list_entry'],
-        'mail_subject_waiting_list': ['event', 'waiting_list_entry'],
+        'mail_text_waiting_list': ['event', 'waiting_list_entry', 'waiting_list_voucher'],
+        'mail_subject_waiting_list': ['event', 'waiting_list_entry', 'waiting_list_voucher'],
         'mail_text_resend_all_links': ['event', 'orders'],
         'mail_subject_resend_all_links': ['event', 'orders'],
         'mail_attach_ical_description': ['event', 'event_or_subevent'],
diff --git a/src/pretix/plugins/sendmail/forms.py b/src/pretix/plugins/sendmail/forms.py
index 67109e77d..ca23bed4b 100644
--- a/src/pretix/plugins/sendmail/forms.py
+++ b/src/pretix/plugins/sendmail/forms.py
@@ -70,14 +70,7 @@ class FormPlaceholderMixin:
         )
 
 
-class MailForm(FormPlaceholderMixin, forms.Form):
-    recipients = forms.ChoiceField(
-        label=_('Send email to'),
-        widget=forms.RadioSelect,
-        initial='orders',
-        choices=[]
-    )
-    sendto = forms.MultipleChoiceField()  # overridden later
+class BaseMailForm(FormPlaceholderMixin, forms.Form):
     subject = forms.CharField(label=_("Subject"))
     message = forms.CharField(label=_("Message"))
     attachment = CachedFileField(
@@ -91,12 +84,100 @@ class MailForm(FormPlaceholderMixin, forms.Form):
         help_text=_('Sending an attachment increases the chance of your email not arriving or being sorted into spam folders. We recommend only using PDFs '
                     'of no more than 2 MB in size.'),
         max_size=settings.FILE_UPLOAD_MAX_SIZE_EMAIL_ATTACHMENT
-    )  # TODO i18n
+    )
+
+    def __init__(self, *args, **kwargs):
+        event = self.event = kwargs.pop('event')
+        context_parameters = kwargs.pop('context_parameters')
+        super().__init__(*args, **kwargs)
+        self.fields['subject'] = I18nFormField(
+            label=_('Subject'),
+            widget=I18nTextInput, required=True,
+            locales=event.settings.get('locales'),
+        )
+        self.fields['message'] = I18nFormField(
+            label=_('Message'),
+            widget=I18nTextarea, required=True,
+            locales=event.settings.get('locales'),
+        )
+        self._set_field_placeholders('subject', context_parameters)
+        self._set_field_placeholders('message', context_parameters)
+
+
+class WaitinglistMailForm(BaseMailForm):
     items = forms.ModelMultipleChoiceField(
         widget=forms.CheckboxSelectMultiple(
             attrs={'class': 'scrolling-multiple-choice'}
         ),
-        label=_('Only send to people who bought'),
+        label=pgettext_lazy('sendmail_form', 'Waiting for'),
+        required=True,
+        queryset=Item.objects.none()
+    )
+    subevent = forms.ModelChoiceField(
+        SubEvent.objects.none(),
+        label=pgettext_lazy('sendmail_form', 'Restrict to a specific event date'),
+        required=False,
+        empty_label=pgettext_lazy('subevent', 'All dates')
+    )
+    subevents_from = forms.SplitDateTimeField(
+        widget=SplitDateTimePickerWidget(),
+        label=pgettext_lazy('sendmail_form', 'Restrict to event dates starting at or after'),
+        required=False,
+    )
+    subevents_to = forms.SplitDateTimeField(
+        widget=SplitDateTimePickerWidget(),
+        label=pgettext_lazy('sendmail_form', 'Restrict to event dates starting before'),
+        required=False,
+    )
+
+    def clean(self):
+        d = super().clean()
+        if d.get('subevent') and (d.get('subevents_from') or d.get('subevents_to')):
+            raise ValidationError(pgettext_lazy('subevent', 'Please either select a specific date or a date range, not both.'))
+        if bool(d.get('subevents_from')) != bool(d.get('subevents_to')):
+            raise ValidationError(pgettext_lazy('subevent', 'If you set a date range, please set both a start and an end.'))
+        return d
+
+    def __init__(self, *args, **kwargs):
+        event = self.event = kwargs['event']
+        super().__init__(*args, **kwargs)
+
+        self.fields['items'].queryset = event.items.all()
+        if not self.initial.get('items'):
+            self.initial['items'] = event.items.all()
+
+        if event.has_subevents:
+            self.fields['subevent'].queryset = event.subevents.all()
+            self.fields['subevent'].widget = Select2(
+                attrs={
+                    'data-model-select2': 'event',
+                    'data-select2-url': reverse('control:event.subevents.select2', kwargs={
+                        'event': event.slug,
+                        'organizer': event.organizer.slug,
+                    }),
+                    'data-placeholder': pgettext_lazy('subevent', 'Date')
+                }
+            )
+            self.fields['subevent'].widget.choices = self.fields['subevent'].choices
+        else:
+            del self.fields['subevent']
+            del self.fields['subevents_from']
+            del self.fields['subevents_to']
+
+
+class OrderMailForm(BaseMailForm):
+    recipients = forms.ChoiceField(
+        label=pgettext_lazy('sendmail_from', 'Send to'),
+        widget=forms.RadioSelect,
+        initial='orders',
+        choices=[]
+    )
+    sendto = forms.MultipleChoiceField()  # overridden later
+    items = forms.ModelMultipleChoiceField(
+        widget=forms.CheckboxSelectMultiple(
+            attrs={'class': 'scrolling-multiple-choice'}
+        ),
+        label=pgettext_lazy('sendmail_form', 'Restrict to products'),
         required=True,
         queryset=Item.objects.none()
     )
@@ -105,31 +186,31 @@ class MailForm(FormPlaceholderMixin, forms.Form):
         required=False
     )
     checkin_lists = SafeModelMultipleChoiceField(queryset=CheckinList.objects.none(), required=False)  # overridden later
-    not_checked_in = forms.BooleanField(label=_("Send to customers not checked in"), required=False)
+    not_checked_in = forms.BooleanField(label=pgettext_lazy('sendmail_from', 'Restrict to recipients without check-in'), required=False)
     subevent = forms.ModelChoiceField(
         SubEvent.objects.none(),
-        label=_('Only send to customers of'),
+        label=pgettext_lazy('sendmail_form', 'Restrict to a specific event date'),
         required=False,
         empty_label=pgettext_lazy('subevent', 'All dates')
     )
     subevents_from = forms.SplitDateTimeField(
         widget=SplitDateTimePickerWidget(),
-        label=pgettext_lazy('subevent', 'Only send to customers of dates starting at or after'),
+        label=pgettext_lazy('sendmail_form', 'Restrict to event dates starting at or after'),
         required=False,
     )
     subevents_to = forms.SplitDateTimeField(
         widget=SplitDateTimePickerWidget(),
-        label=pgettext_lazy('subevent', 'Only send to customers of dates starting before'),
+        label=pgettext_lazy('sendmail_form', 'Restrict to event dates starting before'),
         required=False,
     )
     created_from = forms.SplitDateTimeField(
         widget=SplitDateTimePickerWidget(),
-        label=pgettext_lazy('subevent', 'Only send to customers with orders created after'),
+        label=pgettext_lazy('sendmail_form', 'Restrict to orders created at or after'),
         required=False,
     )
     created_to = forms.SplitDateTimeField(
         widget=SplitDateTimePickerWidget(),
-        label=pgettext_lazy('subevent', 'Only send to customers with orders created before'),
+        label=pgettext_lazy('sendmail_form', 'Restrict to orders created before'),
         required=False,
     )
     attach_tickets = forms.BooleanField(
@@ -147,7 +228,7 @@ class MailForm(FormPlaceholderMixin, forms.Form):
         return d
 
     def __init__(self, *args, **kwargs):
-        event = self.event = kwargs.pop('event')
+        event = self.event = kwargs['event']
         super().__init__(*args, **kwargs)
 
         recp_choices = [
@@ -161,18 +242,6 @@ class MailForm(FormPlaceholderMixin, forms.Form):
             ]
         self.fields['recipients'].choices = recp_choices
 
-        self.fields['subject'] = I18nFormField(
-            label=_('Subject'),
-            widget=I18nTextInput, required=True,
-            locales=event.settings.get('locales'),
-        )
-        self.fields['message'] = I18nFormField(
-            label=_('Message'),
-            widget=I18nTextarea, required=True,
-            locales=event.settings.get('locales'),
-        )
-        self._set_field_placeholders('subject', ['event', 'order', 'position_or_address'])
-        self._set_field_placeholders('message', ['event', 'order', 'position_or_address'])
         choices = [(e, l) for e, l in Order.STATUS_CHOICE if e != 'n']
         choices.insert(0, ('na', _('payment pending (except unapproved)')))
         choices.insert(0, ('pa', _('approval pending')))
@@ -181,7 +250,7 @@ class MailForm(FormPlaceholderMixin, forms.Form):
                 ('overdue', _('pending with payment overdue'))
             )
         self.fields['sendto'] = forms.MultipleChoiceField(
-            label=_("Send to customers with order status"),
+            label=pgettext_lazy('sendmail_from', 'Restrict to orders with status'),
             widget=forms.CheckboxSelectMultiple(
                 attrs={'class': 'scrolling-multiple-choice no-search'}
             ),
@@ -205,11 +274,11 @@ class MailForm(FormPlaceholderMixin, forms.Form):
                     'event': event.slug,
                     'organizer': event.organizer.slug,
                 }),
-                'data-placeholder': _('Send to customers checked in on list'),
+                'data-placeholder': pgettext_lazy('sendmail_from', 'Restrict to recipients with check-in on list')
             }
         )
         self.fields['checkin_lists'].widget.choices = self.fields['checkin_lists'].choices
-        self.fields['checkin_lists'].label = _('Send to customers checked in on list')
+        self.fields['checkin_lists'].label = pgettext_lazy('sendmail_from', 'Restrict to recipients with check-in on list')
 
         if event.has_subevents:
             self.fields['subevent'].queryset = event.subevents.all()
diff --git a/src/pretix/plugins/sendmail/signals.py b/src/pretix/plugins/sendmail/signals.py
index 4a5cd674e..6e3c7e2cf 100644
--- a/src/pretix/plugins/sendmail/signals.py
+++ b/src/pretix/plugins/sendmail/signals.py
@@ -48,10 +48,11 @@ from django_scopes import scope, scopes_disabled
 
 from pretix.base.models import SubEvent
 from pretix.base.signals import (
-    event_copy_data, logentry_display, periodic_task,
+    EventPluginSignal, event_copy_data, logentry_display, periodic_task,
 )
 from pretix.control.signals import nav_event
 from pretix.plugins.sendmail.models import ScheduledMail
+from pretix.plugins.sendmail.views import OrderSendView, WaitinglistSendView
 
 logger = logging.getLogger(__name__)
 
@@ -91,7 +92,7 @@ def control_nav_import(sender, request=None, **kwargs):
                         'event': request.event.slug,
                         'organizer': request.event.organizer.slug,
                     }),
-                    'active': (url.namespace == 'plugins:sendmail' and url.url_name == 'send'),
+                    'active': (url.namespace == 'plugins:sendmail' and url.url_name.startswith('send')),
                 },
                 {
                     'label': _('Automated emails'),
@@ -117,7 +118,8 @@ def control_nav_import(sender, request=None, **kwargs):
 @receiver(signal=logentry_display)
 def pretixcontrol_logentry_display(sender, logentry, **kwargs):
     plains = {
-        'pretix.plugins.sendmail.sent': _('Email was sent'),
+        'pretix.plugins.sendmail.sent': _('Mass email was sent to customers or attendees.'),
+        'pretix.plugins.sendmail.sent.waitinglist': _('Mass email was sent to waiting list entries.'),
         'pretix.plugins.sendmail.order.email.sent': _('The order received a mass email.'),
         'pretix.plugins.sendmail.order.email.sent.attendee': _('A ticket holder of this order received a mass email.'),
         'pretix.plugins.sendmail.rule.added': _('An email rule was created'),
@@ -219,3 +221,17 @@ def sendmail_copy_data_receiver(sender, other, item_map, **kwargs):
         r.save()
         if limit_products:
             r.limit_products.add(*[item_map[p.id] for p in limit_products if p.id in item_map])
+
+
+sendmail_view_classes = EventPluginSignal()
+"""
+This signal allows you to register subclasses of ``pretix.plugins.sendmail.views.BaseSenderView`` that should be
+discovered by this plugin.
+
+As with all plugin signals, the ``sender`` keyword will contain the event.
+"""
+
+
+@receiver(signal=sendmail_view_classes, dispatch_uid="sendmail_register_sendmail_view_classes")
+def register_view_classes(sender, **kwargs):
+    return [OrderSendView, WaitinglistSendView]
diff --git a/src/pretix/plugins/sendmail/tasks.py b/src/pretix/plugins/sendmail/tasks.py
index 0a4cdd453..af04f369d 100644
--- a/src/pretix/plugins/sendmail/tasks.py
+++ b/src/pretix/plugins/sendmail/tasks.py
@@ -44,12 +44,12 @@ from pretix.helpers.format import format_map
 
 
 @app.task(base=ProfiledEventTask, acks_late=True)
-def send_mails(event: Event, user: int, subject: dict, message: dict, orders: list, items: list,
-               recipients: str, filter_checkins: bool, not_checked_in: bool, checkin_lists: list,
-               attachments: list = None, attach_tickets: bool = False) -> None:
+def send_mails_to_orders(event: Event, user: int, subject: dict, message: dict, objects: list, items: list,
+                         recipients: str, filter_checkins: bool, not_checked_in: bool, checkin_lists: list,
+                         attachments: list = None, attach_tickets: bool = False) -> None:
     failures = []
     user = User.objects.get(pk=user) if user else None
-    orders = Order.objects.filter(pk__in=orders, event=event)
+    orders = Order.objects.filter(pk__in=objects, event=event)
     subject = LazyI18nString(subject)
     message = LazyI18nString(message)
 
@@ -138,7 +138,7 @@ def send_mails(event: Event, user: int, subject: dict, message: dict, orders: li
                         locale=o.locale,
                         order=o,
                         attach_tickets=attach_tickets,
-                        attach_cached_files=attachments
+                        attach_cached_files=attachments,
                     )
                     o.log_action(
                         'pretix.plugins.sendmail.order.email.sent',
@@ -151,3 +151,27 @@ def send_mails(event: Event, user: int, subject: dict, message: dict, orders: li
                     )
             except SendMailException:
                 failures.append(o.email)
+
+
+@app.task(base=ProfiledEventTask, acks_late=True)
+def send_mails_to_waitinglist(event: Event, user: int, subject: dict, message: dict, objects: list,
+                              attachments: list = None) -> None:
+    user = User.objects.get(pk=user) if user else None
+    entries = event.waitinglistentries.filter(pk__in=objects).select_related(
+        'subevent'
+    )
+    subject = LazyI18nString(subject)
+    message = LazyI18nString(message)
+
+    for e in entries:
+        e.send_mail(
+            subject,
+            message,
+            get_email_context(
+                event=e.event,
+                waiting_list_entry=e,
+                event_or_subevent=e.subevent or e.event,
+            ),
+            user=user,
+            attach_cached_files=attachments,
+        )
diff --git a/src/pretix/plugins/sendmail/templates/pretixplugins/sendmail/history.html b/src/pretix/plugins/sendmail/templates/pretixplugins/sendmail/history.html
index 57480a9f2..970ba287e 100644
--- a/src/pretix/plugins/sendmail/templates/pretixplugins/sendmail/history.html
+++ b/src/pretix/plugins/sendmail/templates/pretixplugins/sendmail/history.html
@@ -22,33 +22,7 @@
                         {% if log.display %}
                             <br/><span class="fa fa-comment-o fa-fw"></span> {{ log.display }}
                         {% endif %}
-                        <br/><span class="fa fa-tag fa-fw"></span> {% trans "Sent to orders:" %}
-                        {% for status in log.parsed_data.sendto %}
-                            {{ status }}{% if forloop.revcounter > 1 %},{% endif %}
-                        {% endfor %}
-                        {% if log.pdata.items %}
-                            <br/><span class="fa fa-shopping-cart fa-fw"></span> {{ log.pdata.items|join:", " }}
-                        {% endif %}
-                        {% if log.pdata.filter_checkins %}
-                            {% if log.pdata.not_checked_in %}
-                                <br/><span class="fa fa-check-square-o fa-fw"></span> {% trans "All customers not checked in" %}
-                            {% endif %}
-                            {% if log.pdata.checkin_lists %}
-                                <br/><span class="fa fa-check-square-o fa-fw"></span> {{ log.pdata.checkin_lists|join:", " }}
-                            {% endif %}
-                        {% endif %}
-                        {% if log.pdata.subevent_obj %}
-                            <br/><span class="fa fa-calendar fa-fw"></span> {{ log.pdata.subevent_obj }}
-                        {% elif log.pdata.subevents_from %}
-                            <br/><span class="fa fa-calendar fa-fw"></span> {{ log.pdata.subevents_from }} – {{ log.pdata.subevents_to }}
-                        {% endif %}
-                        {% if log.pdata.recipients == "attendees" %}
-                            <br/><span class="fa fa-envelope fa-fw"></span> {% trans "Attendee contact addresses" %}
-                        {% elif log.pdata.recipients == "both" %}
-                            <br/><span class="fa fa-envelope fa-fw"></span> {% trans "All contact addresses" %}
-                        {% else%}
-                            <br/><span class="fa fa-envelope fa-fw"></span> {% trans "Order contact addresses" %}
-                        {% endif %}
+                        {{ log.view.rendered_data }}
                     </p>
                     <p>
                         {% for locale, value in log.pdata.locales.items %}
@@ -58,7 +32,7 @@
                             <pre>{{ value.message|linebreaksbr }}</pre>
                         {% endfor %}
                     </p>
-                    <a href="{% url 'plugins:sendmail:send' organizer=request.event.organizer.slug event=request.event.slug %}?from_log={{ log.id }}">{% trans "Send a new email based on this" %}</a>
+                    <a href="{{ log.view.url }}?from_log={{ log.id }}">{% trans "Send a new email based on this" %}</a>
                 </li>
             {% endfor %}
         </ul>
diff --git a/src/pretix/plugins/sendmail/templates/pretixplugins/sendmail/history_fragment_orders.html b/src/pretix/plugins/sendmail/templates/pretixplugins/sendmail/history_fragment_orders.html
new file mode 100644
index 000000000..ebfb6ca27
--- /dev/null
+++ b/src/pretix/plugins/sendmail/templates/pretixplugins/sendmail/history_fragment_orders.html
@@ -0,0 +1,28 @@
+{% load i18n %}
+<br/><span class="fa fa-tag fa-fw"></span> {% trans "Sent to orders:" %}
+{% for status in log.parsed_data.sendto %}
+    {{ status }}{% if forloop.revcounter > 1 %},{% endif %}
+{% endfor %}
+{% if log.pdata.items %}
+    <br/><span class="fa fa-shopping-cart fa-fw"></span> {{ log.pdata.items|join:", " }}
+{% endif %}
+{% if log.pdata.filter_checkins %}
+    {% if log.pdata.not_checked_in %}
+        <br/><span class="fa fa-check-square-o fa-fw"></span> {% trans "All customers not checked in" %}
+    {% endif %}
+    {% if log.pdata.checkin_lists %}
+        <br/><span class="fa fa-check-square-o fa-fw"></span> {{ log.pdata.checkin_lists|join:", " }}
+    {% endif %}
+{% endif %}
+{% if log.pdata.subevent_obj %}
+    <br/><span class="fa fa-calendar fa-fw"></span> {{ log.pdata.subevent_obj }}
+{% elif log.pdata.subevents_from %}
+    <br/><span class="fa fa-calendar fa-fw"></span> {{ log.pdata.subevents_from }} – {{ log.pdata.subevents_to }}
+{% endif %}
+{% if log.pdata.recipients == "attendees" %}
+    <br/><span class="fa fa-envelope fa-fw"></span> {% trans "Attendee contact addresses" %}
+{% elif log.pdata.recipients == "both" %}
+    <br/><span class="fa fa-envelope fa-fw"></span> {% trans "All contact addresses" %}
+{% else%}
+    <br/><span class="fa fa-envelope fa-fw"></span> {% trans "Order contact addresses" %}
+{% endif %}
diff --git a/src/pretix/plugins/sendmail/templates/pretixplugins/sendmail/history_fragment_waitinglist.html b/src/pretix/plugins/sendmail/templates/pretixplugins/sendmail/history_fragment_waitinglist.html
new file mode 100644
index 000000000..8bea24ac7
--- /dev/null
+++ b/src/pretix/plugins/sendmail/templates/pretixplugins/sendmail/history_fragment_waitinglist.html
@@ -0,0 +1,9 @@
+{% load i18n %}
+{% if log.pdata.items %}
+    <br/><span class="fa fa-shopping-cart fa-fw"></span> {{ log.pdata.items|join:", " }}
+{% endif %}
+{% if log.pdata.subevent_obj %}
+    <br/><span class="fa fa-calendar fa-fw"></span> {{ log.pdata.subevent_obj }}
+{% elif log.pdata.subevents_from %}
+    <br/><span class="fa fa-calendar fa-fw"></span> {{ log.pdata.subevents_from }} – {{ log.pdata.subevents_to }}
+{% endif %}
diff --git a/src/pretix/plugins/sendmail/templates/pretixplugins/sendmail/index.html b/src/pretix/plugins/sendmail/templates/pretixplugins/sendmail/index.html
new file mode 100644
index 000000000..e491905a9
--- /dev/null
+++ b/src/pretix/plugins/sendmail/templates/pretixplugins/sendmail/index.html
@@ -0,0 +1,16 @@
+{% extends "pretixcontrol/event/base.html" %}
+{% load i18n %}
+{% block title %}{% trans "Send out emails" %}{% endblock %}
+{% block content %}
+    <h1>{% trans "Send out emails" %}</h1>
+    <div class="list-group large-link-group">
+        {% for view in views %}
+            <a class="list-group-item" href="{{ view.url }}">
+                <h4>{{ view.title }}</h4>
+                <p>
+                    {{ view.description }}
+                </p>
+            </a>
+        {% endfor %}
+    </div>
+{% endblock %}
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 4250aa6c7..c562fb959 100644
--- a/src/pretix/plugins/sendmail/templates/pretixplugins/sendmail/send_form.html
+++ b/src/pretix/plugins/sendmail/templates/pretixplugins/sendmail/send_form.html
@@ -4,7 +4,10 @@
 {% load humanize %}
 {% block title %}{% trans "Send out emails" %}{% endblock %}
 {% block content %}
-    <h1>{% trans "Send out emails" %}</h1>
+    <h1>
+        {% trans "Send out emails" %}
+        <small>{{ view_title }}</small>
+    </h1>
     {% block inner %}
         <form class="form-horizontal" method="post" action="" enctype="multipart/form-data">
             {% csrf_token %}
@@ -20,40 +23,16 @@
             {% bootstrap_form_errors form %}
             <fieldset>
                 <legend>{% trans "Recipients" %}</legend>
-                {% bootstrap_field form.recipients layout='horizontal' %}
-                {% bootstrap_field form.sendto layout='horizontal' %}
-                {% if form.subevent %}
-                    {% bootstrap_field form.subevent layout='horizontal' %}
-                    {% bootstrap_field form.subevents_from layout='horizontal' %}
-                    {% bootstrap_field form.subevents_to layout='horizontal' %}
-                {% endif %}
-                {% bootstrap_field form.created_from layout='horizontal' %}
-                {% bootstrap_field form.created_to layout='horizontal' %}
-                {% bootstrap_field form.items layout='horizontal' %}
-                <div class="row">
-                    <div class="col-md-9 col-md-offset-3">
-                        <div class="panel-group">
-                            <div class="panel panel-default">
-                                <div class="panel-heading">
-                                    <label data-toggle="collapse" data-target="#checkin_filter">
-                                        {{ form.filter_checkins }} {{ form.filter_checkins.label }}
-                                    </label>
-                                </div>
-                                <div id="checkin_filter" class="panel-body panel-collapse collapse {% if form.filter_checkins.value %} in {% else %} out {% endif %}">
-                                    {% bootstrap_field form.not_checked_in layout='horizontal' %}
-                                    {% bootstrap_field form.checkin_lists layout='horizontal' %}
-                                </div>
-                            </div>
-                        </div>
-                    </div>
-                </div>
+                {% include form_fragment_name with form=form %}
             </fieldset>
             <fieldset {% if is_preview %}class="hidden"{% endif %}>
                 <legend>{% trans "Content" %}</legend>
                 {% bootstrap_field form.subject layout='horizontal' %}
                 {% bootstrap_field form.message layout='horizontal' %}
                 {% bootstrap_field form.attachment layout='horizontal' %}
-                {% bootstrap_field form.attach_tickets layout='horizontal' %}
+                {% if form.attach_tickets %}
+                    {% bootstrap_field form.attach_tickets layout='horizontal' %}
+                {% endif %}
             </fieldset>
             {% if is_preview %}
             <fieldset>
@@ -97,12 +76,7 @@
                     </button>
                     <button type="submit" class="btn btn-danger btn-save" name="action" value="send">
                         <span class="fa fa-send" aria-hidden="true"></span>
-                        {% trans "Send" %}
-                        ({% blocktrans trimmed with number=order_count|default_if_none:0|intcomma count c=order_count|default_if_none:0 %}
-                            {{ number }} matching order
-                        {% plural %}
-                            {{ number }} matching orders
-                        {% endblocktrans %})
+                        {% trans "Send" %} ({{ match_size }})
                     </button>
                 {% endif %}
             </div>
diff --git a/src/pretix/plugins/sendmail/templates/pretixplugins/sendmail/send_form_fragment_orders.html b/src/pretix/plugins/sendmail/templates/pretixplugins/sendmail/send_form_fragment_orders.html
new file mode 100644
index 000000000..2bb3e4bf3
--- /dev/null
+++ b/src/pretix/plugins/sendmail/templates/pretixplugins/sendmail/send_form_fragment_orders.html
@@ -0,0 +1,29 @@
+{% load i18n %}
+{% load bootstrap3 %}
+{% bootstrap_field form.recipients layout='horizontal' %}
+{% bootstrap_field form.sendto layout='horizontal' %}
+{% if form.subevent %}
+    {% bootstrap_field form.subevent layout='horizontal' %}
+    {% bootstrap_field form.subevents_from layout='horizontal' %}
+    {% bootstrap_field form.subevents_to layout='horizontal' %}
+{% endif %}
+{% bootstrap_field form.created_from layout='horizontal' %}
+{% bootstrap_field form.created_to layout='horizontal' %}
+{% bootstrap_field form.items layout='horizontal' %}
+<div class="row">
+    <div class="col-md-9 col-md-offset-3">
+        <div class="panel-group">
+            <div class="panel panel-default">
+                <div class="panel-heading">
+                    <label data-toggle="collapse" data-target="#checkin_filter">
+                        {{ form.filter_checkins }} {{ form.filter_checkins.label }}
+                    </label>
+                </div>
+                <div id="checkin_filter" class="panel-body panel-collapse collapse {% if form.filter_checkins.value %} in {% else %} out {% endif %}">
+                    {% bootstrap_field form.not_checked_in layout='horizontal' %}
+                    {% bootstrap_field form.checkin_lists layout='horizontal' %}
+                </div>
+            </div>
+        </div>
+    </div>
+</div>
diff --git a/src/pretix/plugins/sendmail/templates/pretixplugins/sendmail/send_form_fragment_waitinglist.html b/src/pretix/plugins/sendmail/templates/pretixplugins/sendmail/send_form_fragment_waitinglist.html
new file mode 100644
index 000000000..ac2731bae
--- /dev/null
+++ b/src/pretix/plugins/sendmail/templates/pretixplugins/sendmail/send_form_fragment_waitinglist.html
@@ -0,0 +1,8 @@
+{% load i18n %}
+{% load bootstrap3 %}
+{% bootstrap_field form.items layout='horizontal' %}
+{% if form.subevent %}
+    {% bootstrap_field form.subevent layout='horizontal' %}
+    {% bootstrap_field form.subevents_from layout='horizontal' %}
+    {% bootstrap_field form.subevents_to layout='horizontal' %}
+{% endif %}
diff --git a/src/pretix/plugins/sendmail/urls.py b/src/pretix/plugins/sendmail/urls.py
index ae58d2be9..d972f438d 100644
--- a/src/pretix/plugins/sendmail/urls.py
+++ b/src/pretix/plugins/sendmail/urls.py
@@ -40,8 +40,12 @@ from . import views
 from .api import RuleViewSet
 
 urlpatterns = [
-    re_path(r'^control/event/(?P<organizer>[^/]+)/(?P<event>[^/]+)/sendmail/$', views.SenderView.as_view(),
+    re_path(r'^control/event/(?P<organizer>[^/]+)/(?P<event>[^/]+)/sendmail/$', views.IndexView.as_view(),
             name='send'),
+    re_path(r'^control/event/(?P<organizer>[^/]+)/(?P<event>[^/]+)/sendmail/orders/$', views.OrderSendView.as_view(),
+            name='send.orders'),
+    re_path(r'^control/event/(?P<organizer>[^/]+)/(?P<event>[^/]+)/sendmail/waitinglist/$', views.WaitinglistSendView.as_view(),
+            name='send.waitinglist'),
     re_path(r'^control/event/(?P<organizer>[^/]+)/(?P<event>[^/]+)/sendmail/history/', views.EmailHistoryView.as_view(),
             name='history'),
     re_path(r'^control/event/(?P<organizer>[^/]+)/(?P<event>[^/]+)/sendmail/rules/create', views.CreateRule.as_view(),
diff --git a/src/pretix/plugins/sendmail/views.py b/src/pretix/plugins/sendmail/views.py
index 957107238..602a21847 100644
--- a/src/pretix/plugins/sendmail/views.py
+++ b/src/pretix/plugins/sendmail/views.py
@@ -38,15 +38,17 @@ import logging
 import bleach
 import dateutil
 from django.contrib import messages
+from django.contrib.humanize.templatetags.humanize import intcomma
 from django.db import transaction
 from django.db.models import Count, Exists, Max, Min, OuterRef, Q
 from django.http import Http404, HttpResponseRedirect
 from django.shortcuts import get_object_or_404, redirect
+from django.template.loader import get_template
 from django.urls import reverse
 from django.utils.functional import cached_property
 from django.utils.timezone import now
-from django.utils.translation import gettext_lazy as _
-from django.views.generic import DeleteView, FormView, ListView
+from django.utils.translation import gettext_lazy as _, ngettext
+from django.views.generic import DeleteView, FormView, ListView, TemplateView
 
 from pretix.base.email import get_available_placeholders
 from pretix.base.i18n import LazyI18nString, language
@@ -55,7 +57,9 @@ from pretix.base.models.event import SubEvent
 from pretix.base.templatetags.rich_text import markdown_compile_email
 from pretix.control.permissions import EventPermissionRequiredMixin
 from pretix.control.views import CreateView, PaginationMixin, UpdateView
-from pretix.plugins.sendmail.tasks import send_mails
+from pretix.plugins.sendmail.tasks import (
+    send_mails_to_orders, send_mails_to_waitinglist,
+)
 
 from ...helpers.format import format_map
 from . import forms
@@ -64,59 +68,104 @@ from .models import Rule, ScheduledMail
 logger = logging.getLogger('pretix.plugins.sendmail')
 
 
-class SenderView(EventPermissionRequiredMixin, FormView):
+class IndexView(EventPermissionRequiredMixin, TemplateView):
+    template_name = 'pretixplugins/sendmail/index.html'
+    permission = 'can_change_orders'
+
+    def get_context_data(self, **kwargs):
+        from .signals import sendmail_view_classes
+        classes = []
+        for recv, resp in sendmail_view_classes.send(self.request.event):
+            if isinstance(resp, (list, tuple)):
+                classes += resp
+            else:
+                classes.append(resp)
+        return super().get_context_data(**kwargs, views=[
+            {
+                'title': cls.TITLE,
+                'description': cls.DESCRIPTION,
+                'url': cls.get_url(self.request.event)
+            } for cls in classes
+        ])
+
+
+class BaseSenderView(EventPermissionRequiredMixin, FormView):
+    # These parameters usually SHOULD NOT be overridden
     template_name = 'pretixplugins/sendmail/send_form.html'
     permission = 'can_change_orders'
-    form_class = forms.MailForm
+
+    # These parameters MUST be overridden by subclasses
+    form_fragment_name = None
+    context_parameters = ['event']
+    task = None
+
+    # These parameters MUST be overriden by subclasses in a way that allows static access
+
+    ACTION_TYPE = None
+    TITLE = ""
+    DESCRIPTION = ""
+
+    # The following methods MUST be overridden by subclasses
+
+    @staticmethod
+    def get_url(self, event):
+        """Returns the URL for this view for a given event."""
+        raise NotImplementedError
+
+    def get_object_queryset(self, form):
+        """Returns a queryset of objects that will become recipients."""
+        return Order.objects.none()
+
+    def describe_match_size(self, cnt):
+        """Returns a short human-readable description of the recipient set, such as '3 attendees'."""
+        raise NotImplementedError
+
+    @classmethod
+    def show_history_meta_data(cls, logentry, _cache_store):
+        """Returns an HTML component for the history view."""
+        raise NotImplementedError
+
+    # The following methods MAY be overridden by subclasses
+
+    def initial_from_logentry(self, logentry):
+        return {
+            'message': LazyI18nString(logentry.parsed_data['message']),
+            'subject': LazyI18nString(logentry.parsed_data['subject']),
+        }
+
+    def get_success_url(self):
+        return self.request.get_full_path()
+
+    def get_task_kwargs(self, form, objects):
+        kwargs = {
+            'event': self.request.event.pk,
+            'user': self.request.user.pk,
+            'subject': form.cleaned_data['subject'].data,
+            'message': form.cleaned_data['message'].data,
+            'objects': [o.pk for o in objects],
+        }
+        attachment = form.cleaned_data.get('attachment')
+        if attachment is not None and attachment is not False:
+            kwargs['attachments'] = [form.cleaned_data['attachment'].id]
+        return kwargs
+
+    # The following methods SHOULD NOT Be overridden by subclasses, but in some cases it may be necessary
 
     def get_form_kwargs(self):
         kwargs = super().get_form_kwargs()
         kwargs['event'] = self.request.event
+        kwargs['context_parameters'] = self.context_parameters
         if 'from_log' in self.request.GET:
             try:
                 from_log_id = self.request.GET.get('from_log')
                 logentry = LogEntry.objects.get(
                     id=from_log_id,
                     event=self.request.event,
-                    action_type='pretix.plugins.sendmail.sent'
+                    action_type=self.ACTION_TYPE
                 )
                 kwargs['initial'] = {
-                    'recipients': logentry.parsed_data.get('recipients', 'orders'),
-                    'message': LazyI18nString(logentry.parsed_data['message']),
-                    'subject': LazyI18nString(logentry.parsed_data['subject']),
-                    'sendto': logentry.parsed_data['sendto'],
+                    **self.initial_from_logentry(logentry),
                 }
-                if 'items' in logentry.parsed_data:
-                    kwargs['initial']['items'] = self.request.event.items.filter(
-                        id__in=[a['id'] for a in logentry.parsed_data['items']]
-                    )
-                elif logentry.parsed_data.get('item'):
-                    kwargs['initial']['items'] = self.request.event.items.filter(
-                        id=logentry.parsed_data['item']['id']
-                    )
-                if 'checkin_lists' in logentry.parsed_data:
-                    kwargs['initial']['checkin_lists'] = self.request.event.checkin_lists.filter(
-                        id__in=[c['id'] for c in logentry.parsed_data['checkin_lists']]
-                    )
-                kwargs['initial']['filter_checkins'] = logentry.parsed_data.get('filter_checkins', False)
-                kwargs['initial']['not_checked_in'] = logentry.parsed_data.get('not_checked_in', False)
-                if logentry.parsed_data.get('subevents_from'):
-                    kwargs['initial']['subevents_from'] = dateutil.parser.parse(logentry.parsed_data['subevents_from'])
-                if logentry.parsed_data.get('subevents_to'):
-                    kwargs['initial']['subevents_to'] = dateutil.parser.parse(logentry.parsed_data['subevents_to'])
-                if logentry.parsed_data.get('created_from'):
-                    kwargs['initial']['created_from'] = dateutil.parser.parse(logentry.parsed_data['created_from'])
-                if logentry.parsed_data.get('created_to'):
-                    kwargs['initial']['created_to'] = dateutil.parser.parse(logentry.parsed_data['created_to'])
-                if logentry.parsed_data.get('attach_tickets'):
-                    kwargs['initial']['attach_tickets'] = logentry.parsed_data['attach_tickets']
-                if logentry.parsed_data.get('subevent'):
-                    try:
-                        kwargs['initial']['subevent'] = self.request.event.subevents.get(
-                            pk=logentry.parsed_data['subevent']['id']
-                        )
-                    except SubEvent.DoesNotExist:
-                        pass
             except LogEntry.DoesNotExist:
                 raise Http404(_('You supplied an invalid log entry ID'))
         return kwargs
@@ -126,6 +175,170 @@ class SenderView(EventPermissionRequiredMixin, FormView):
         return super().form_invalid(form)
 
     def form_valid(self, form):
+        objects = self.get_object_queryset(form)
+        ocnt = objects.count()
+
+        self.output = {}
+        if not ocnt:
+            messages.error(self.request, _('There are no matching recipients for your selection.'))
+            self.request.POST = self.request.POST.copy()
+            self.request.POST.pop("action", "")
+            return self.get(self.request, *self.args, **self.kwargs)
+
+        if self.request.POST.get("action") != "send":
+            for l in self.request.event.settings.locales:
+                with language(l, self.request.event.settings.region):
+                    context_dict = {}
+                    for k, v in get_available_placeholders(self.request.event, self.context_parameters).items():
+                        context_dict[k] = '<span class="placeholder" title="{}">{}</span>'.format(
+                            _('This value will be replaced based on dynamic parameters.'),
+                            v.render_sample(self.request.event)
+                        )
+
+                    subject = bleach.clean(form.cleaned_data['subject'].localize(l), tags=[])
+                    preview_subject = format_map(subject, context_dict)
+                    message = form.cleaned_data['message'].localize(l)
+                    preview_text = markdown_compile_email(format_map(message, context_dict))
+
+                    self.output[l] = {
+                        'subject': _('Subject: {subject}').format(subject=preview_subject),
+                        'html': preview_text,
+                        'attachment': form.cleaned_data.get('attachment')
+                    }
+
+            self.object_count = ocnt
+            return self.get(self.request, *self.args, **self.kwargs)
+
+        self.task.apply_async(
+            kwargs=self.get_task_kwargs(form, objects)
+        )
+        self.request.event.log_action(
+            self.ACTION_TYPE,
+            user=self.request.user,
+            data=dict(form.cleaned_data)
+        )
+        messages.success(self.request, _('Your message has been queued and will be sent to the contact addresses of %s '
+                                         'in the next few minutes.') % self.describe_match_size(len(objects)))
+
+        return redirect(self.get_success_url())
+
+    def get_context_data(self, *args, **kwargs):
+        ctx = super().get_context_data(*args, **kwargs)
+        ctx['output'] = getattr(self, 'output', None)
+        ctx['match_size'] = self.describe_match_size(getattr(self, 'object_count', None))
+        ctx['form_fragment_name'] = self.form_fragment_name
+        ctx['is_preview'] = self.request.method == 'POST' and self.request.POST.get('action') == 'preview' and ctx['form'].is_valid()
+        ctx['view_title'] = self.TITLE
+        return ctx
+
+    def get_form(self, form_class=None):
+        f = super().get_form(form_class)
+        if self.request.method == 'POST' and self.request.POST.get('action') == 'preview':
+            if f.is_valid():
+                for fname, field in f.fields.items():
+                    field.widget.attrs['disabled'] = 'disabled'
+        return f
+
+
+class OrderSendView(BaseSenderView):
+    form_class = forms.OrderMailForm
+    form_fragment_name = "pretixplugins/sendmail/send_form_fragment_orders.html"
+    context_parameters = ['event', 'order', 'position_or_address']
+    task = send_mails_to_orders
+
+    ACTION_TYPE = 'pretix.plugins.sendmail.sent'
+    TITLE = _("Orders or attendees")
+    DESCRIPTION = _("Send an email to every customer, or to every person a ticket has been "
+                    "purchased for, or a combination of both.")
+
+    @classmethod
+    def show_history_meta_data(cls, logentry, _cache_store):
+        if 'itemcache' not in _cache_store:
+            _cache_store['itemcache'] = {
+                i.pk: str(i) for i in logentry.event.items.all()
+            }
+        if 'checkin_list_cache' not in _cache_store:
+            _cache_store['checkin_list_cache'] = {
+                i.pk: str(i) for i in logentry.event.checkin_lists.all()
+            }
+        if 'status' not in _cache_store:
+            status = dict(Order.STATUS_CHOICE)
+            status['overdue'] = _('pending with payment overdue')
+            status['na'] = _('payment pending (except unapproved)')
+            status['pa'] = _('approval pending')
+            status['r'] = status['c']
+            _cache_store['status'] = status
+
+        tpl = get_template('pretixplugins/sendmail/history_fragment_orders.html')
+        logentry.pdata['sendto'] = [
+            _cache_store['status'][s] for s in logentry.pdata['sendto']
+        ]
+        logentry.pdata['items'] = [
+            _cache_store['itemcache'].get(i['id'], '?') for i in logentry.pdata.get('items', [])
+        ]
+        logentry.pdata['checkin_lists'] = [
+            _cache_store['checkin_list_cache'].get(i['id'], '?')
+            for i in logentry.pdata.get('checkin_lists', []) if i['id'] in _cache_store['checkin_list_cache']
+        ]
+        if logentry.pdata.get('subevent'):
+            try:
+                logentry.pdata['subevent_obj'] = logentry.event.subevents.get(pk=logentry.pdata['subevent']['id'])
+            except SubEvent.DoesNotExist:
+                pass
+        return tpl.render({
+            'log': logentry,
+        })
+
+    @classmethod
+    def get_url(cls, event):
+        return reverse(
+            'plugins:sendmail:send.orders',
+            kwargs={
+                'event': event.slug,
+                'organizer': event.organizer.slug,
+            }
+        )
+
+    def initial_from_logentry(self, logentry: LogEntry):
+        initial = super().initial_from_logentry(logentry)
+        if 'recipients' in logentry.parsed_data:
+            initial['recipients'] = logentry.parsed_data.get('recipients', 'orders')
+        if 'sendto' in logentry.parsed_data:
+            initial['sendto'] = logentry.parsed_data.get('recipients', 'sendto')
+        if 'items' in logentry.parsed_data:
+            initial['items'] = self.request.event.items.filter(
+                id__in=[a['id'] for a in logentry.parsed_data['items']]
+            )
+        elif logentry.parsed_data.get('item'):
+            initial['items'] = self.request.event.items.filter(
+                id=logentry.parsed_data['item']['id']
+            )
+        if 'checkin_lists' in logentry.parsed_data:
+            initial['checkin_lists'] = self.request.event.checkin_lists.filter(
+                id__in=[c['id'] for c in logentry.parsed_data['checkin_lists']]
+            )
+        initial['filter_checkins'] = logentry.parsed_data.get('filter_checkins', False)
+        initial['not_checked_in'] = logentry.parsed_data.get('not_checked_in', False)
+        if logentry.parsed_data.get('subevents_from'):
+            initial['subevents_from'] = dateutil.parser.parse(logentry.parsed_data['subevents_from'])
+        if logentry.parsed_data.get('subevents_to'):
+            initial['subevents_to'] = dateutil.parser.parse(logentry.parsed_data['subevents_to'])
+        if logentry.parsed_data.get('created_from'):
+            initial['created_from'] = dateutil.parser.parse(logentry.parsed_data['created_from'])
+        if logentry.parsed_data.get('created_to'):
+            initial['created_to'] = dateutil.parser.parse(logentry.parsed_data['created_to'])
+        if logentry.parsed_data.get('attach_tickets'):
+            initial['attach_tickets'] = logentry.parsed_data['attach_tickets']
+        if logentry.parsed_data.get('subevent'):
+            try:
+                initial['subevent'] = self.request.event.subevents.get(
+                    pk=logentry.parsed_data['subevent']['id']
+                )
+            except SubEvent.DoesNotExist:
+                pass
+        return initial
+
+    def get_object_queryset(self, form):
         qs = Order.objects.filter(event=self.request.event)
         statusq = Q(status__in=form.cleaned_data['sendto'])
         if 'overdue' in form.cleaned_data['sendto']:
@@ -189,88 +402,111 @@ class SenderView(EventPermissionRequiredMixin, FormView):
         if form.cleaned_data.get('created_to'):
             opq = opq.filter(order__datetime__lt=form.cleaned_data.get('created_to'))
 
-        orders = orders.annotate(match_pos=Exists(opq)).filter(match_pos=True).distinct()
+        return orders.annotate(match_pos=Exists(opq)).filter(match_pos=True).distinct()
 
-        ocnt = orders.count()
+    def describe_match_size(self, cnt):
+        return ngettext(
+            '%(number)s matching order',
+            '%(number)s matching orders',
+            cnt or 0,
+        ) % {
+            'number': intcomma(cnt or 0),
+        }
 
-        self.output = {}
-        if not ocnt:
-            messages.error(self.request, _('There are no orders matching this selection.'))
-            self.request.POST = self.request.POST.copy()
-            self.request.POST.pop("action", "")
-            return self.get(self.request, *self.args, **self.kwargs)
-
-        if self.request.POST.get("action") != "send":
-            for l in self.request.event.settings.locales:
-                with language(l, self.request.event.settings.region):
-                    context_dict = {}
-                    for k, v in get_available_placeholders(self.request.event, ['event', 'order',
-                                                                                'position_or_address']).items():
-                        context_dict[k] = '<span class="placeholder" title="{}">{}</span>'.format(
-                            _('This value will be replaced based on dynamic parameters.'),
-                            v.render_sample(self.request.event)
-                        )
-
-                    subject = bleach.clean(form.cleaned_data['subject'].localize(l), tags=[])
-                    preview_subject = format_map(subject, context_dict)
-                    message = form.cleaned_data['message'].localize(l)
-                    preview_text = markdown_compile_email(format_map(message, context_dict))
-
-                    self.output[l] = {
-                        'subject': _('Subject: {subject}').format(subject=preview_subject),
-                        'html': preview_text,
-                        'attachment': form.cleaned_data.get('attachment')
-                    }
-
-            self.order_count = ocnt
-            return self.get(self.request, *self.args, **self.kwargs)
-
-        kwargs = {
+    def get_task_kwargs(self, form, objects):
+        kwargs = super().get_task_kwargs(form, objects)
+        kwargs.update({
             'recipients': form.cleaned_data['recipients'],
-            'event': self.request.event.pk,
-            'user': self.request.user.pk,
-            'subject': form.cleaned_data['subject'].data,
-            'message': form.cleaned_data['message'].data,
-            'orders': [o.pk for o in orders],
             'items': [i.pk for i in form.cleaned_data.get('items')],
             'not_checked_in': form.cleaned_data.get('not_checked_in'),
             'checkin_lists': [i.pk for i in form.cleaned_data.get('checkin_lists')],
             'filter_checkins': form.cleaned_data.get('filter_checkins'),
             'attach_tickets': form.cleaned_data.get('attach_tickets'),
+        })
+        return kwargs
+
+
+class WaitinglistSendView(BaseSenderView):
+    form_class = forms.WaitinglistMailForm
+    form_fragment_name = "pretixplugins/sendmail/send_form_fragment_waitinglist.html"
+    context_parameters = ['event', 'waiting_list_entry', 'event_or_subevent']
+    task = send_mails_to_waitinglist
+
+    ACTION_TYPE = 'pretix.plugins.sendmail.sent.waitinglist'
+    TITLE = _("Waiting list")
+    DESCRIPTION = _("Send an email to every person currently waiting to receive a voucher through the waiting "
+                    "list feature.")
+
+    @classmethod
+    def show_history_meta_data(cls, logentry, _cache_store):
+        if 'itemcache' not in _cache_store:
+            _cache_store['itemcache'] = {
+                i.pk: str(i) for i in logentry.event.items.all()
+            }
+
+        tpl = get_template('pretixplugins/sendmail/history_fragment_waitinglist.html')
+        logentry.pdata['items'] = [
+            _cache_store['itemcache'].get(i['id'], '?') for i in logentry.pdata.get('items', [])
+        ]
+        if logentry.pdata.get('subevent'):
+            try:
+                logentry.pdata['subevent_obj'] = logentry.event.subevents.get(pk=logentry.pdata['subevent']['id'])
+            except SubEvent.DoesNotExist:
+                pass
+        return tpl.render({
+            'log': logentry,
+        })
+
+    @classmethod
+    def get_url(cls, event):
+        return reverse(
+            'plugins:sendmail:send.waitinglist',
+            kwargs={
+                'event': event.slug,
+                'organizer': event.organizer.slug,
+            }
+        )
+
+    def initial_from_logentry(self, logentry: LogEntry):
+        initial = super().initial_from_logentry(logentry)
+        if 'items' in logentry.parsed_data:
+            initial['items'] = self.request.event.items.filter(
+                id__in=[a['id'] for a in logentry.parsed_data['items']]
+            )
+        if logentry.parsed_data.get('subevents_from'):
+            initial['subevents_from'] = dateutil.parser.parse(logentry.parsed_data['subevents_from'])
+        if logentry.parsed_data.get('subevents_to'):
+            initial['subevents_to'] = dateutil.parser.parse(logentry.parsed_data['subevents_to'])
+        if logentry.parsed_data.get('subevent'):
+            try:
+                initial['subevent'] = self.request.event.subevents.get(
+                    pk=logentry.parsed_data['subevent']['id']
+                )
+            except SubEvent.DoesNotExist:
+                pass
+        return initial
+
+    def get_object_queryset(self, form):
+        qs = self.request.event.waitinglistentries.filter(voucher__isnull=True)
+
+        qs = qs.filter(item__in=[i.pk for i in form.cleaned_data.get('items')])
+        if form.cleaned_data.get('subevent'):
+            qs = qs.filter(subevent=form.cleaned_data.get('subevent'))
+        if form.cleaned_data.get('subevents_from'):
+            qs = qs.filter(subevent__date_from__gte=form.cleaned_data.get('subevents_from'))
+        if form.cleaned_data.get('subevents_to'):
+            qs = qs.filter(subevent__date_from__lt=form.cleaned_data.get('subevents_to'))
+
+        return qs
+
+    def describe_match_size(self, cnt):
+        return ngettext(
+            '%(number)s waiting list entry',
+            '%(number)s waiting list entries',
+            cnt or 0,
+        ) % {
+            'number': intcomma(cnt or 0),
         }
-        attachment = form.cleaned_data.get('attachment')
-        if attachment is not None and attachment is not False:
-            kwargs['attachments'] = [form.cleaned_data['attachment'].id]
-
-        send_mails.apply_async(
-            kwargs=kwargs
-        )
-        self.request.event.log_action('pretix.plugins.sendmail.sent',
-                                      user=self.request.user,
-                                      data=dict(form.cleaned_data))
-        messages.success(self.request, _('Your message has been queued and will be sent to the contact addresses of %d '
-                                         'orders in the next few minutes.') % len(orders))
-
-        return redirect(
-            'plugins:sendmail:send',
-            event=self.request.event.slug,
-            organizer=self.request.event.organizer.slug
-        )
-
-    def get_context_data(self, *args, **kwargs):
-        ctx = super().get_context_data(*args, **kwargs)
-        ctx['output'] = getattr(self, 'output', None)
-        ctx['order_count'] = getattr(self, 'order_count', None)
-        ctx['is_preview'] = self.request.method == 'POST' and self.request.POST.get('action') == 'preview' and ctx['form'].is_valid()
-        return ctx
-
-    def get_form(self, form_class=None):
-        f = super().get_form(form_class)
-        if self.request.method == 'POST' and self.request.POST.get('action') == 'preview':
-            if f.is_valid():
-                for fname, field in f.fields.items():
-                    field.widget.attrs['disabled'] = 'disabled'
-        return f
 
 
 class EmailHistoryView(EventPermissionRequiredMixin, ListView):
@@ -280,27 +516,30 @@ class EmailHistoryView(EventPermissionRequiredMixin, ListView):
     context_object_name = 'logs'
     paginate_by = 5
 
+    @cached_property
+    def type_map(self):
+        from .signals import sendmail_view_classes
+        classes = []
+        for recv, resp in sendmail_view_classes.send(self.request.event):
+            if isinstance(resp, (list, tuple)):
+                classes += resp
+            else:
+                classes.append(resp)
+        return {
+            cls.ACTION_TYPE: cls
+            for cls in classes
+        }
+
     def get_queryset(self):
         qs = LogEntry.objects.filter(
             event=self.request.event,
-            action_type='pretix.plugins.sendmail.sent'
+            action_type__in=self.type_map.keys(),
         ).select_related('event', 'user')
         return qs
 
     def get_context_data(self, **kwargs):
         ctx = super().get_context_data()
-
-        itemcache = {
-            i.pk: str(i) for i in self.request.event.items.all()
-        }
-        checkin_list_cache = {
-            i.pk: str(i) for i in self.request.event.checkin_lists.all()
-        }
-        status = dict(Order.STATUS_CHOICE)
-        status['overdue'] = _('pending with payment overdue')
-        status['na'] = _('payment pending (except unapproved)')
-        status['pa'] = _('approval pending')
-        status['r'] = status['c']
+        _cache = {}
         for log in ctx['logs']:
             log.pdata = log.parsed_data
             log.pdata['locales'] = {}
@@ -309,21 +548,11 @@ class EmailHistoryView(EventPermissionRequiredMixin, ListView):
                     'message': msg,
                     'subject': log.pdata['subject'][locale]
                 }
-            log.pdata['sendto'] = [
-                status[s] for s in log.pdata['sendto']
-            ]
-            log.pdata['items'] = [
-                itemcache.get(i['id'], '?') for i in log.pdata.get('items', [])
-            ]
-            log.pdata['checkin_lists'] = [
-                checkin_list_cache.get(i['id'], '?')
-                for i in log.pdata.get('checkin_lists', []) if i['id'] in checkin_list_cache
-            ]
-            if log.pdata.get('subevent'):
-                try:
-                    log.pdata['subevent_obj'] = self.request.event.subevents.get(pk=log.pdata['subevent']['id'])
-                except SubEvent.DoesNotExist:
-                    pass
+            log.view = {
+                'url': self.type_map[log.action_type].get_url(self.request.event),
+                'title': self.type_map[log.action_type].TITLE,
+                'rendered_data': self.type_map[log.action_type].show_history_meta_data(log, _cache)
+            }
 
         return ctx
 
diff --git a/src/pretix/static/pretixcontrol/scss/main.scss b/src/pretix/static/pretixcontrol/scss/main.scss
index 512b56b50..9fb0ca74e 100644
--- a/src/pretix/static/pretixcontrol/scss/main.scss
+++ b/src/pretix/static/pretixcontrol/scss/main.scss
@@ -792,6 +792,27 @@ tbody th {
     background: $table-bg-hover;
 }
 
+.large-link-group {
+    a.list-group-item {
+        &::before {
+            font-family: FontAwesome;
+            font-size: 30px;
+            content: $fa-var-chevron-right;
+            float: right;
+            color: $link-color;
+        }
+        h4 {
+            color: $link-color;
+        }
+        &:hover &::before {
+            color: $link-hover-color;
+        }
+        &:hover h4 {
+            color: $link-hover-color;
+        }
+    }
+}
+
 
 .withoutjs {
     display: none !important;
diff --git a/src/tests/plugins/sendmail/test_sendmail.py b/src/tests/plugins/sendmail/test_sendmail.py
index cd25e0248..ff7ef79c9 100644
--- a/src/tests/plugins/sendmail/test_sendmail.py
+++ b/src/tests/plugins/sendmail/test_sendmail.py
@@ -68,13 +68,21 @@ def subevent(event):
     event.has_subevents = True
     event.save()
     se = event.subevents.create(name='se1', date_from=now())
-
     return se
 
 
+@pytest.fixture
+def waitinglistentry(event, item):
+    return event.waitinglistentries.create(
+        item=item,
+        created=now(),
+        email='john@example.org',
+    )
+
+
 @pytest.mark.django_db
 def test_sendmail_view(logged_in_client, sendmail_url, expected=200):
-    response = logged_in_client.get(sendmail_url)
+    response = logged_in_client.get(sendmail_url + 'orders/')
 
     assert response.status_code == expected
 
@@ -82,7 +90,7 @@ def test_sendmail_view(logged_in_client, sendmail_url, expected=200):
 @pytest.mark.django_db
 def test_sendmail_simple_case(logged_in_client, sendmail_url, event, order, pos):
     djmail.outbox = []
-    response = logged_in_client.post(sendmail_url,
+    response = logged_in_client.post(sendmail_url + 'orders/',
                                      {'sendto': 'na',
                                       'action': 'send',
                                       'recipients': 'orders',
@@ -109,7 +117,7 @@ def test_sendmail_simple_case(logged_in_client, sendmail_url, event, order, pos)
 @pytest.mark.django_db
 def test_sendmail_email_not_sent_if_order_not_match(logged_in_client, sendmail_url, event, order, pos):
     djmail.outbox = []
-    response = logged_in_client.post(sendmail_url,
+    response = logged_in_client.post(sendmail_url + 'orders/',
                                      {'sendto': 'p',
                                       'action': 'send',
                                       'recipients': 'orders',
@@ -126,7 +134,7 @@ def test_sendmail_email_not_sent_if_order_not_match(logged_in_client, sendmail_u
 @pytest.mark.django_db
 def test_sendmail_preview(logged_in_client, sendmail_url, event, order, pos):
     djmail.outbox = []
-    response = logged_in_client.post(sendmail_url,
+    response = logged_in_client.post(sendmail_url + 'orders/',
                                      {'sendto': 'na',
                                       'recipients': 'orders',
                                       'items': pos.item_id,
@@ -144,7 +152,7 @@ def test_sendmail_preview(logged_in_client, sendmail_url, event, order, pos):
 @pytest.mark.django_db
 def test_sendmail_invalid_data(logged_in_client, sendmail_url, event, order, pos):
     djmail.outbox = []
-    response = logged_in_client.post(sendmail_url,
+    response = logged_in_client.post(sendmail_url + 'orders/',
                                      {'sendto': 'na',
                                       'action': 'send',
                                       'recipients': 'orders',
@@ -172,7 +180,7 @@ def test_sendmail_multi_locales(logged_in_client, sendmail_url, event, item):
                                  locale='de')
         OrderPosition.objects.create(order=o, item=item, price=13)
 
-    response = logged_in_client.post(sendmail_url,
+    response = logged_in_client.post(sendmail_url + 'orders/',
                                      {'sendto': 'p',
                                       'action': 'send',
                                       'recipients': 'orders',
@@ -211,7 +219,7 @@ def test_sendmail_subevents(logged_in_client, sendmail_url, event, order, pos):
     op.save()
 
     djmail.outbox = []
-    response = logged_in_client.post(sendmail_url,
+    response = logged_in_client.post(sendmail_url + 'orders/',
                                      {'sendto': 'na',
                                       'action': 'send',
                                       'recipients': 'orders',
@@ -226,7 +234,7 @@ def test_sendmail_subevents(logged_in_client, sendmail_url, event, order, pos):
     assert len(djmail.outbox) == 1
 
     djmail.outbox = []
-    response = logged_in_client.post(sendmail_url,
+    response = logged_in_client.post(sendmail_url + 'orders/',
                                      {'sendto': 'na',
                                       'action': 'send',
                                       'recipients': 'orders',
@@ -248,7 +256,7 @@ def test_sendmail_subevents(logged_in_client, sendmail_url, event, order, pos):
 @pytest.mark.django_db
 def test_sendmail_placeholder(logged_in_client, sendmail_url, event, order, pos):
     djmail.outbox = []
-    response = logged_in_client.post(sendmail_url,
+    response = logged_in_client.post(sendmail_url + 'orders/',
                                      {'sendto': 'na',
                                       'recipients': 'orders',
                                       'items': pos.item_id,
@@ -272,7 +280,7 @@ def test_sendmail_attendee_mails(logged_in_client, sendmail_url, event, order, p
     p.save()
 
     djmail.outbox = []
-    response = logged_in_client.post(sendmail_url,
+    response = logged_in_client.post(sendmail_url + 'orders/',
                                      {'sendto': 'na',
                                       'action': 'send',
                                       'recipients': 'attendees',
@@ -297,7 +305,7 @@ def test_sendmail_both_mails(logged_in_client, sendmail_url, event, order, pos):
     p.save()
 
     djmail.outbox = []
-    response = logged_in_client.post(sendmail_url,
+    response = logged_in_client.post(sendmail_url + 'orders/',
                                      {'sendto': 'na',
                                       'action': 'send',
                                       'recipients': 'both',
@@ -325,7 +333,7 @@ def test_sendmail_both_but_same_address(logged_in_client, sendmail_url, event, o
     p.save()
 
     djmail.outbox = []
-    response = logged_in_client.post(sendmail_url,
+    response = logged_in_client.post(sendmail_url + 'orders/',
                                      {'sendto': 'na',
                                       'action': 'send',
                                       'recipients': 'both',
@@ -350,7 +358,7 @@ def test_sendmail_attendee_fallback(logged_in_client, sendmail_url, event, order
     p.save()
 
     djmail.outbox = []
-    response = logged_in_client.post(sendmail_url,
+    response = logged_in_client.post(sendmail_url + 'orders/',
                                      {'sendto': 'na',
                                       'action': 'send',
                                       'recipients': 'attendees',
@@ -380,7 +388,7 @@ def test_sendmail_attendee_product_filter(logged_in_client, sendmail_url, event,
         )
 
         djmail.outbox = []
-        response = logged_in_client.post(sendmail_url,
+        response = logged_in_client.post(sendmail_url + 'orders/',
                                          {'sendto': 'na',
                                           'action': 'send',
                                           'recipients': 'attendees',
@@ -409,7 +417,7 @@ def test_sendmail_attendee_checkin_filter(logged_in_client, sendmail_url, event,
         Checkin.objects.create(position=pos2, list=chkl2)
 
     djmail.outbox = []
-    response = logged_in_client.post(sendmail_url,
+    response = logged_in_client.post(sendmail_url + 'orders/',
                                      {'sendto': 'na',
                                       'action': 'send',
                                       'recipients': 'attendees',
@@ -428,7 +436,7 @@ def test_sendmail_attendee_checkin_filter(logged_in_client, sendmail_url, event,
     assert '/order/' not in djmail.outbox[0].body
 
     djmail.outbox = []
-    response = logged_in_client.post(sendmail_url,
+    response = logged_in_client.post(sendmail_url + 'orders/',
                                      {'sendto': 'na',
                                       'action': 'send',
                                       'recipients': 'attendees',
@@ -447,7 +455,7 @@ def test_sendmail_attendee_checkin_filter(logged_in_client, sendmail_url, event,
     assert '/order/' not in djmail.outbox[0].body
 
     djmail.outbox = []
-    response = logged_in_client.post(sendmail_url,
+    response = logged_in_client.post(sendmail_url + 'orders/',
                                      {'sendto': 'na',
                                       'action': 'send',
                                       'recipients': 'attendees',
@@ -467,7 +475,7 @@ def test_sendmail_attendee_checkin_filter(logged_in_client, sendmail_url, event,
 
     # Test that filtering is ignored if filter_checkins is not set
     djmail.outbox = []
-    response = logged_in_client.post(sendmail_url,
+    response = logged_in_client.post(sendmail_url + 'orders/',
                                      {'sendto': 'na',
                                       'action': 'send',
                                       'recipients': 'attendees',
@@ -489,7 +497,7 @@ def test_sendmail_attendee_checkin_filter(logged_in_client, sendmail_url, event,
 
     # Test that filtering is ignored if filter_checkins is not set
     djmail.outbox = []
-    response = logged_in_client.post(sendmail_url,
+    response = logged_in_client.post(sendmail_url + 'orders/',
                                      {'sendto': 'na',
                                       'action': 'send',
                                       'recipients': 'attendees',
@@ -508,3 +516,28 @@ def test_sendmail_attendee_checkin_filter(logged_in_client, sendmail_url, event,
     assert '/order/' not in djmail.outbox[1].body
     to_emails = set(*zip(*[mail.to for mail in djmail.outbox]))
     assert to_emails == {'attendee1@dummy.test', 'attendee2@dummy.test'}
+
+
+@pytest.mark.django_db
+def test_waitinglist_sendmail_simple_case(logged_in_client, sendmail_url, event, waitinglistentry):
+    djmail.outbox = []
+    response = logged_in_client.post(sendmail_url + 'waitinglist/',
+                                     {'action': 'send',
+                                      'items': waitinglistentry.item_id,
+                                      'subject_0': 'Test subject',
+                                      'message_0': 'This is a test file for sending mails.',
+                                      },
+                                     follow=True)
+    assert response.status_code == 200
+    assert 'alert-success' in response.rendered_content
+
+    assert len(djmail.outbox) == 1
+    assert djmail.outbox[0].to == [waitinglistentry.email]
+    assert djmail.outbox[0].subject == 'Test subject'
+    assert 'This is a test file for sending mails.' in djmail.outbox[0].body
+
+    url = sendmail_url + 'history/'
+    response = logged_in_client.get(url)
+
+    assert response.status_code == 200
+    assert 'Test subject' in response.rendered_content